night boat tours in chicago

Private Events

• Accessibility
• Terms Of Use
• Privacy Policy

Help us win Best Boat Tour in USA Today's Best of 2024 poll! Vote every day here !

Architecture Tour

TripAdvisor users rank the Chicago Architecture Center River Cruise aboard Chicago's First Lady as the city's #1 boat tour.

There’s one sure recipe to make your business or social event even more memorable – just add water and Chicago’s First Lady!

Recalling the handsome elegance of 20th century luxury yachts, our vessels are sure to make an impression. Choose from seven perfectly sized ships for your private event.

Your wedding is the start of your lifelong journey together, so begin that journey in a truly memorable way - a wedding cruise down the Chicago River.

Evening River Cruise

Experience our renowned daytime CAC River Cruise in the glow of the setting sun. Take in the city’s magnificent architecture bathed in golden light as it begins its transition from day to night.

“The very best city tour I have been on in my life! We were in America for a month and this was our best morning.” - JurassicBill TripAdvisor, Dorset UK

- Latest Articles -

A Memorable Mother's Day in Chicago

This Mother’s Day, embark on a beautiful day celebrating Mom with all the best Chicago has to offer.…

Vote Today To Make Chicago’s #1 Boat Tour The #1 Boat Tour In The U.S.

Show your Chicago Pride by voting the Chicago Architecture Center Boat Tour aboard Chicago’s First Lady,…

Top Occasions to Celebrate on the Chicago River

The Chicago River, with its winding beauty amidst the city’s architectural wonders, offers a unique backdrop…

See Our Full Blog

"What an amazing experience, this tour brings all the beautiful architecture and history to life.” - Rachel M Yelp, Arizona, USA

Awesome, you're subscribed!

Thanks for subscribing! Look out for your first newsletter in your inbox soon!

The best of Chicago for free.

Sign up for our email to enjoy Chicago without spending a thing (as well as some options when you’re feeling flush).

Déjà vu! We already have this email. Try another?

By entering your email address you agree to our Terms of Use and Privacy Policy and consent to receive emails from Time Out about news, events, offers and partner promotions.

Love the mag?

Our newsletter hand-delivers the best bits to your inbox. Sign up to unlock our digital magazines and also receive the latest news, events, offers and partner promotions.

• Things to Do
• Food & Drink
• Time Out Market
• Coca-Cola Foodmarks
• Attractions
• Los Angeles

Get us in your inbox

🙌 Awesome, you're subscribed!

The 15 best boat tours in Chicago

See the skyline from dazzling new vantage points aboard one of the best boat tours in Chicago

Sure, walks along Michigan Avenue and State Street are nice and rooftop bars offer plenty of pretty sights – but the best way to see downtown Chicago is from the water. Both the Chicago River and Lake Michigan offer unparalleled vantage points for taking in the city’s world-famous architecture and the breathtaking Chicago skyline , with many of the tours providing unique insights into the city’s culture and history.

From architecture tours and history lessons to  straightforward sightseeing affairs , romantic excursions and pirate-themed family fun, there's a Chicago cruise for every groove. Below we’ve got the essential list of the city’s finest waterborne tours, including tall-mast ships and glitzy speed boats. Bon voyage!  

RECOMMENDED: Find more to explore with the best things to do in Chicago Plan your trip with the  best hotels in Chicago

How do we determine the cream of the crop? Our staff picks combine the top, most recent reviews with some of our personal favorites to make sure you get the best deal on the web. Throughout this article, you may notice some affiliate links – these have no influence on our editorial content – we pinky swear. For more information, see our  affiliate guidelines .

An email you’ll actually love

Best Chicago boat tours

1.  1.5-Hour Guided Architecture River Cruise

Departing from Navy Pier's Polk Bros Park or the northeast corner of the Michigan Avenue Bridge, this 60-minute trip packs in all of the architectural sights that visitors want to see. Tour guides highlight more than 40 towering Chicago landmarks, including the Tribune Tower, the Wrigley Building, and Marina City (a.k.a. "The Corncobs" or " The Wilco Building "). 

Don't miss:  Locally sourced food and drink from the boat bar.  

2.  Seadog River and Lake Architectural Tour

There are few more iconic Chicago sights than seeing the bright yellow Seadog speeding around town. Combining speed and sightseeing, Seadog’s architecture tour whizzes guests past the likes of the Willis Tower and Lyric Opera, all while arming you with an impressive load of facts about the Windy City. And after this blustery 75-minute tour has finished traversing the Chicago River, it ends with a thrilling whizz across Lake Michigan, past Museum Campus, and Grant Park. This one departs from Seadog’s dock at Navy Pier throughout the summer months.

Don't miss:  Local beer, spirits and Garrett's Popcorn at the boat bar.

3.  Wendella: Chicago's Original Family-Friendly Architecture Tour

If you're weighing your options, Wendella's architecture tour (which it claims is Chicago's original ) is another way to explore all of the beautiful structures that line the river. Over the course of the 90-minute tour, you'll navigate all three branches of the Chicago River, while your guide fills you in on the stories behind some of the skyline's most prominent edifices. This tour departs from the Wendella Dock, located at the northwest corner of the Michigan Avenue Bridge at the foot of the Wrigley Building.

Don't miss: Live commentary from the tour guide, with material to entertain the whole family. 

4.  1.5-Hour Romantic Sunset Cruise

How do you end the perfect day of sightseeing? With the perfect sunset, obvs. Setting off from Wendella Dock (at the northwest corner of the Michigan Avenue Bridge at the foot of the Wrigley Building), this 90-minute cruise will breeze along Lake Michigan as the glint of the sun on Chicago's skyscrapers is replaced by twinkling city lights. 

Don't miss: Toasting to the end of the day with wine, local beer and hand-crafted cocktails.

5.  Tall Ship Windy Architecture & Skyline Sailing Tour

Let the wind carry you to stunning views of the city from aboard the Tall Ship Windy, a four-masted, 148-foot topsail schooner. The 75-minute trip cruise brings guests on a scenic route running along the Lake Michigan shoreline, where you can take in lovely skyline vistas and glimpses of the sunset. Head to the onboard bar to find snacks and drinks for sale. 

Don't miss:  Bring the kids for the special pirate-themed cruise, featuring  tales of swashbuckling  on the Great Lakes.  

6.  Seadog Speedboat Tour

If you balk at the idea of traipsing around museums and galleries all day with just your legs for locomotion, this whistle-stop boat ride is the tour for you. See every worthy Chicago landmark in 30 minutes on Seadog’s speedboat, which can sometimes feel like a floating rollercoaster. Launching from Navy Pier, the captain will efficiently guide you (with a running commentary) around Lake Michigan, past Museum Campus, Magnificent Mile, Grant Park, and more.

Don't miss: Upgrade to the Extreme Thrill Ride, which includes full 360° spins and more. 

7.  Lake Michigan Skyline Sightseeing Cruise

Want to see Chicago from the water but don't have much time to spare? You can peep the skyline in just 30 minutes on Shoreline's Classic Lake Tour, which departs from Navy Pier and boasts some of the best views you'll find on Lake Michigan. The commentary on the city's architecture and history is pre-recorded, so you won't miss out on any information because your guide ran out of time (and if you've heard it before, you can sit back and enjoy those sweet, sweet sights).

Don't miss: Proceeding straight to the boarding line with a barcode that lets you skip the ticket office. 

8.  Lake Michigan Gourmet Dinner Cruise

Enjoy a three-course gourmet dinner on the water in the Odyssey Chicago, where you can enjoy breathtaking views of the skyline surrounding you. Departing from Navy Pier, this cruise includes a dinner with freshly prepared entrées, mains, and desserts. The 2.5 or 3-hour ride takes you around Lake Michigan, with a cash bar to keep the drinks flowing throughout your meal.

Don't miss: The live DJ set and unlimited tea and coffee.

9.  Chicago's Lake Michigan Kayak Tour

If you want to couple a workout with your sightseeing, consider touring Lake Michigan by kayak. The rental lasts one hour and if you've never kayaked before, don't worry – tandem kayaks are available for less experienced guests. The meeting point is at Ohio Street Beach and you'll be provided with a life jacket on arrival before paddling out onto Chicago's most incredible river view.

Don't miss: Take a break along the urban beachfront, with the chance to also rent stand-up paddle boards.  

10.  Lake Michigan Buffet Brunch Cruise

If you're looking for dinner with a view, you could do worse than watching the sunset against the skyline aboard this 2.5 or 3-hour Lake Michigan brunch, lunch, or dinner cruise. Grab a group of friends and book a table – ideally one with a window-facing view—for a buffet-style meal before making your way to the dancefloor for an evening of DJ-curated music. Unlimited coffee, tea, and water will be on hand.

Don't miss: Creative signature cocktails at the bar. 

11.  Lake Michigan Odyssey Gourmet Lunch Cruise

Why settle for lunch at a land-bound restaurant when you could eat your meal on Lake Michigan? The Odyssey's lunch cruise includes a three-course meal and all the coffee, hot tea, iced tea and water you can drink. Visit the cash bar to buy wine, beer and cocktails and enjoy the views on this two-hour tour.

Don't miss: Dance on the top deck to tunes played out by the onboard DJ. 

12.  Chicago Fireboat Tours Historical and Architectural Cruise

Hosted on the bright red Fred A. Busse Fireboat – which served the Chicago Fire Department until 1981 – this architectural tour of the Chicago River lasts anywhere from 90 minutes to two hours. A docent will fill you in on the history of buildings lining the river as well as the story of the boat you've boarded, which formerly traveled the city's waterways to fight fires. 

Don't miss: Check out the vintage firefighting artifacts and photos on board. 

13.  Lady Grebe Chicago River Experience

Want to feel extra posh? Grab a group of up to six friends and book a private cruise aboard Lady Grebe, a 48-foot vintage yacht that can be reserved for two-hour trips along the Chicago River. The reservation comes with a premium drinks package and you can also opt to kick things up a notch with picnic baskets full of food or full-service catering. 

Don't miss:  Book a Chicago Architecture Center docent to give a guided tour for an educational twist.

14.  Chicago Electric Boat Company Tour

Go your own way. Be your own captain. That’s what’s on offer with this Chicago River tour. The Chicago Electric Boat Company lets passengers steer the ship themselves (if they’ve got a valid driver’s license and watched a 10-minute tutorial, that is), allowing total freedom on the Windy City’s waterways. If you’re looking to still have some kind of tour, you can hire a personal tour guide—and we haven’t even gotten to the best bit. These boats are all electric, so they’re a little bit more environmentally friendly, too.

Don't miss: Hot tub boat rentals are also available.

15.  Chicago Architecture Center River Cruise Aboard Chicago’s First Lady

There's a reason the Chicago Architecture Foundation's beloved tour has been named the Best Boat Tour in the U.S.  The center’s official tour goes into detail on more than 50 buildings both on the riverfront and beyond. In doing so, they give a fascinating history of the city and those that built it—plus you can easily upgrade your ticket to include entry to just Chicago Architecture Center itself. It’s a proper design enthusiast’s dream. This one leaves from the Chicago First Lady Cruises dock and lasts around 90 minutes. 

Don't miss:  Gather friends for the serene evening cruise for just a few dollars more.

GYG Chicago TTD

[image] [title]

Discover Time Out original video

• Press office
• Investor relations
• Work for Time Out
• Editorial guidelines
• Privacy notice
• Do not sell my information
• Cookie policy
• Accessibility statement
• Terms of use
• Copyright agent
• Modern slavery statement
• Manage cookies
• Advertising

Time Out products

• Time Out Worldwide

Time Out magazine

Chicago Architecture Center River Cruise Aboard Chicago's First Lady

The only Chicago River Cruise named to the Top 10 Boat Tours in North America—3 years in a row!

Buy tickets

“So worth it. This was a highlight of our trip. Just beautiful. Very interesting info, too! We learned a lot and had a great time.” - Mandfamily404

“An absolute pleasure! Best money spent, great time enjoyed by all. The scenery was spectacular, family friendly, romantic, and so easy to do. We went back to back.” - Anthony D

“Amazing experience - fantastic commentary!! Would definitely recommend to anyone visiting Chicago. A must-do trip.” -Dalesboy

#1 Rated Boat Cruise in Chicago!

Led by the Chicago Architecture Center's expertly trained docent volunteers, this 90-minute cruise reveals fascinating stories behind Chicago's majestic buildings in a way no other tour can.

Learn about the architects who created our city's magnificent buildings—and the stories behind them. Experience why the CAC's boat cruise is rated the best year after year.

This classic tour aboard the city's most luxurious fleet, is a must for out-of-town visitors and Chicagoans alike.

Tickets start at $53.85.

Get More Info

EVENING CRUISES AVAILABLE

The city's most popular tour is now offered in the evening. Serene and bathed in softer light, the city's architecture takes on a whole new life in the setting sun.

VISIT THE CENTER

For the ultimate Chicago architecture experience, take the river cruise AND visit the Chicago Architecture Center—you'll save $9!

NOW IN 4 LANGUAGES

Continental French, Latin American Spanish, Japanese and Korean translation available via the "Listen Everywhere" app.

Highlights of this tour

Chicago Riverwalk

1 w. lower wacker drive.

Strolling along Chicago’s beautiful Riverwalk, it’s hard to imagine just how much things have changed…

Skidmore, Owings & Merrill

Architect/firm.

Skidmore, Owings & Merrill (SOM) was founded in 1936 by Louis Skidmore and Nathaniel Owings. Partner…

trunnion bascule bridge

trunnion is a French word for "stump" or pivot point; bascule is a French word for "see-saw"; a trunnion…

Tribune Tower

435 n. michigan ave..

In 1922, on the occasion of its 75th anniversary, the Chicago Tribune announced an international competition…

London Guarantee Building

360 n. michigan ave..

Located where Fort Dearborn once stood, the London Guarantee & Accident Building is one of four structures…

330 North Wabash / AMA Plaza (IBM Plaza)

330 n. wabash ave..

One of the last American projects designed by Ludwig Mies van der Rohe, this powerful Modernist structure…

Ludwig Mies van der Rohe

It’s difficult to imagine what the skyline of Chicago might look like without architect Ludwig Mies van…

Arts and Crafts

The Arts and Crafts movement originated in England in the mid-19th century as an antidote to the dehumanizing…

150 North Riverside

150 n. riverside.

Gravity-defying 150 North Riverside has already taken its rightful place among Chicago’s architectural…

a large vertical, concrete pier, cast in place and used in a foundation where the soil is unstable

333 West Wacker

333 w. wacker dr..

When you’ve got it, you’ve got it—and 333 West Wacker has it.

Apple Michigan Avenue

401 n. michigan ave..

Foster + Partners’ Apple Michigan Avenue store is an impressive, airy glass box with a curved-edge…

Merchandise Mart

222 w. merchandise mart plaza.

Size has always mattered in the Midwest.

THE 5 BEST Chicago Night Tours

Night tours in chicago.

• Sightseeing Tours
• Historical & Heritage Tours
• Night Tours
• Up to 1 hour
• 1 to 4 hours
• 4 hours to 1 day
• 5.0 of 5 bubbles
• 4.0 of 5 bubbles & up
• 3.0 of 5 bubbles & up
• 2.0 of 5 bubbles & up
• Likely to Sell Out
• The ranking of tours, activities, and experiences available on Tripadvisor is determined by several factors including the revenue generated by Tripadvisor from these bookings, the frequency of user clicks, and the volume and quality of customer reviews. Occasionally, newly listed offerings may be prioritized and appear higher in the list. The specific placement of these new listings may vary.

1. Chicago: Gangsters and Ghosts Walking Tour

2. Chicago 3D Fireworks Cruise

3. Chicago by Night: 90 Minute River and Lakefront Cruise

4. Chicago Evening Crime Tour by Bus

5. Big Bus Chicago: Sunset Tour by Open-Top Bus

6. Chicago Hauntings Original Ghost Bus Tour

7. Private Evening Sail in Chicago Ending with Navy Pier Fireworks

Keep the fun going with other experiences in the area.

Murder Mystery Detective Experience Skokie, Il

Best of the West Brewery Excursion with beer tastings

Explore Naperville with a Scavenger Hunt by Zombie Scavengers

Fun Scavenger Hunt in Joliet by Zombie Scavengers

Sunday Afternoon Countryside Cruise (Winery, Distillery, and Brewery)

Elgin City Scavenger Hunt Excursion by Zombie Scavengers

Unique Scavenger Hunt Experience in Aurora by Zombie Scavengers

New Buffalo Bash Scavenger Hunt

Downtown Kenosha Urban Art and Photography Walking Tour

What travelers are saying.

Protect Your Trip »

The 7 best chicago boat tours of 2024: river & lake cruises.

Enjoy architectural boat tours, kayak excursions, speedboat rides and more.

Best Chicago Boat Tours

Courtesy of Tall Ship Windy

If you're hoping to see as much of Chicago as you can in a short amount of time, you may want to sign up for a boat tour. During each tour, you'll learn the historical significance of the skyline's iconic buildings while enjoying breathtaking views of the Windy City. Considering traveler reviews and expert opinion, U.S. News selected the best Chicago boat tours, ranging from an architectural boat tour on the river to a thrilling speedboat ride on Lake Michigan.

Editor’s Pick: Wendella Boats – Chicago River Architecture Tour

Price: Adults from $44; kids from $20 Duration: 1.5 hours

U.S. News independently paid to send Cortney Fries , an award-winning writer based in Chicago, on this tour to provide readers with an unbiased, first-hand perspective of what to expect. The Wendella Boats Chicago River Architecture Tour was selected by our team as an Editor’s Pick thanks to its popularity and favorable user reviews.

Cruise three branches of the Chicago River as you take in views of famous Chicago landmarks, such as the Willis Tower and Merchandise Mart. A knowledgeable guide provides an overview of the architecture and interesting lessons in Chicago history along the way. For instance, did you know that the Lyric Opera House was built in the shape of a giant throne, or that the Chicago River is the only natural river reversed by humankind? Learn about: the four stars on the Chicago flag and what they represent, the legend of the O’Leary cow starting the Great Chicago Fire, the statue atop the Chicago Board of Trade and Chicago’s famous drawbridges.

Refreshments and snacks are sold on board. Sit on the top deck to listen to the live tour with unobstructed views, but bring a jacket or sun hat if it’s cool or sunny. Climate-controlled seating is offered below, as are restrooms. Tours are generally available daily beginning at 9:30 a.m., with multiple departures throughout the day and evening. If you’re short on time or traveling with kids, the 45-minute version of this architecture tour may be your best option.

Cortney Fries

Why we love it:

• The Chicago River Architecture Tour is one of the best ways to learn about and explore Chicago sans crowds. 
• Guides are engaging, informative and also provide ideas for other places to visit during your trip. 
• Tours depart from Michigan Avenue near the Wrigley Building, where there are plenty of shopping and dining options nearby. Arrive early so you can enjoy the area and give yourself enough time to find parking.

– Cortney Fries

Check prices & availability on:

Tall Ship Windy – Chicago Skyline Sail

Price: Adults from $49; kids from $39 Duration: 75 minutes

Tall Ship Windy's Chicago Skyline Sail introduces you to the beauty and splendor of Chicago's world-famous buildings aboard the company's four-masted schooner. On the sightseeing tour, you'll learn interesting facts about the history of this renowned waterfront and its skyline, as well as the people who built it. Travelers love the experience, describing the crew and the schooner as incredible. They recommend booking one of the sunset sails for photo-worthy views.

Tours depart from Navy Pier daily from May through September at 1, 3, 5 and 7 p.m. Note that the 1 p.m. sail is all about the history of piracy in the area. Tall Ship Windy also offers nighttime cruises on select days to correspond with Navy Pier's seasonal Fireworks at the Pier show.

Chicago Architecture Foundation Center River Cruise

Price: Adults from $54; kids from $24 Duration: 1.5 hours

Hop aboard Chicago's First Lady for a tour of the Windy City's spectacular skyline. With one of the Chicago Architecture Center's volunteer docents guiding your trip, you'll learn the architectural and cultural history of more than 50 of Chicago's iconic buildings. Boats are equipped with open-air upper decks, climate-controlled lower cabins, full-service bars and restrooms. Travelers say this architectural boat tour is not to be missed and describe it as a family-friendly experience with spectacular views. They also rave about the insightful, entertaining tour guides who provide a wealth of information.

Cruises generally depart daily from 9 a.m. to 8 p.m., though exact times may vary by day. For an additional $5, you can gain access to the Chicago Architecture Center (which saves you $9 on center admission).

Getty Images

City Experiences by Hornblower – Chicago Seadog Lakefront Speedboat Tour

Price: Adults from $35; children from $25 Duration: 30 minutes

This speedboat tour departs from popular Navy Pier, taking travelers on a fast-paced, 30-minute ride along Lake Michigan's shores. During the cruise, an expert guide will share the history of Chicago and the landmarks that created its iconic skyline. Along with the entertaining commentary, you'll enjoy photo-worthy views of lakefront attractions. Reviewers rave about the tour, saying that the views are superb and the speedboat makes for a thrilling ride.

The tour, which operates from March through October or early November, departs hourly every day starting as early as 11 a.m.; exact departure times vary by day. Keep in mind that the tour is not recommended for pregnant women or people with neck or back injuries. Prefer a more low-key ride? The company also offers brunch, lunch and dinner cruises on larger vessels, along with architectural boat tours.

Urban Kayaks – Historic Chicago Tour

Price: Singles from $65; tandems from $130 Duration: 2 hours

Travelers angling for an active way to see the Chicago River should book this guided kayak outing. You'll learn about Chicago's contemporary urban landscape – and the historical significance of many of its buildings – while you paddle alongside an expert guide. What's more, the tour is suitable for novice and experienced kayakers alike. According to the company, you should expect to get wet and will want to dress accordingly. Reviewers enjoy seeing the city from their kayaks and say you'll pass beautiful and romantic views along the way. They also appreciate the attentive, friendly guides.

Tours are available daily at 11 a.m. and 3 p.m. from May through September. If you'd rather paddle the lake, consider renting a kayak from the company or signing up for its paddleboarding class.

Shoreline Sightseeing – Skyline Lake Tour

Price: Adults from $30; kids from $12 Duration: 30 minutes

Sit back, relax and take in the dramatic scenery of the Chicago skyline with this tour of Lake Michigan. The prerecorded narration will help you learn about Chicago's most famous buildings, such as the Willis Tower, and how they came to life. Along the short cruise, you'll have just enough time to take in the views and enjoy a drink or snack from the bar. Visitors love the tour for the views and history lesson, though some complain it was difficult to hear the narration from the back of the boat. They also advise future riders to bring a jacket because it gets cold on the water.

Tours depart daily in the spring, summer and early fall multiple times a day, weather permitting. Shoreline Sightseeing also offers architecture tours on the Chicago River.

Tours & Boats – 90-Minute Architecture Boat Tour

Price: Adults from $49; kids from $25 Duration: 1.5 hours

Tour-takers say this boat ride is entertaining and educational thanks to the informed guides. You'll see Chicago's many famous buildings up close as guides tell stories of the city's history. Plus, the tour takes you to the locks on the river's main branch, Chinatown in the south and Goose Island in the north.

Cruise departures vary by month and day. Boats depart from River City Marina, which is about a mile west of Grant Park. For several reviewers, the boat's departure point was another reason to book with Tours & Boats as it offers better parking options than some of the other river cruise companies in the city. Tours & Boats also operates private tours.

You may also be interested in:

• The Best Chicago Tours
• The Best Chicago Walking Tours
• The Best Chicago Segway Tours
• Best Hotels in Chicago
• Best Things to Do in Chicago

Tags: Tours , Chicago , Travel , Vacations , Illinois Vacations , US Vacations , Midwest Vacations

World's Best Places To Visit

• # 1 South Island, New Zealand
• # 4 Bora Bora

If you make a purchase from our site, we may earn a commission. This does not affect the quality or independence of our editorial content.

You May Also Like

The best whale watching in santa barbara.

John Rodwan May 29, 2024

The Best Travel Purses

Rachael Hood May 24, 2024

The Best Beach Games

Gwen Pratesi May 24, 2024

The Best Branson Shows

Carrie A. Back May 23, 2024

The Best Beach Toys for Kids

Amanda Norcross May 23, 2024

The Best Charleston Tours

John Rodwan May 23, 2024

The Best Savannah Tours

John Rodwan and Ann Henson May 23, 2024

The Best NYC Dinner Cruises

Jessica Colley Clarke May 23, 2024

The Best Cooler Bags

Sharael Kolberg May 22, 2024

The Best Beach Blankets

Gwen Pratesi and Sharael Kolberg May 22, 2024

Your guide to Chicago lake and river cruises

One of the best ways to see Chicago is from the water. The city is home to two stunning waterfronts — the Chicago River and Lake Michigan — and each offers plenty of cruise options. Admire the skyline on a lakefront cruise, learn about the city’s iconic architecture on a Chicago River cruise, enjoy dinner and dancing aboard an all-glass vessel, sip cocktails on a tiki-themed boat, paddle your own kayak — the options are truly endless. Here’s your guide to Chicago lake and river cruises, boat tours, dinner cruises, and beyond.

See it all with Shoreline Sightseeing

One of Chicago’s classic cruise options, Shoreline Sightseeing covers all the bases. Their ultra-popular Architecture River Tour takes you on all three branches of the historic Chicago River takes you past dozens of landmark buildings.

They also offer skyline lake tours, plus specialty cruises and holiday events. Hop on a boat at Navy Pier or on Michigan Avenue.

Dine on the water with City Experiences

City Experiences dining cruises are the perfect way to create a memorable moment in Chicago. Choose from a river or lake dining cruise, complete with delicious cuisine, cocktails, and entertainment.

Their glass-enclosed river vessel is particularly stunning. It offers passengers panoramic views of the city’s most iconic buildings as you glide along the Chicago River. They also offer lakefront brunch and dinner cruise options that depart from Navy Pier.

Entertain the family with Wendella Boats

For three generations, Wendella Tours and Cruises has been cruising the Chicago waterways. With its variety of tour options, cruise times and lengths, and a heated, enclosed cabin, Wendella is a great choice for families looking for flexibility. Choose from lake & river architecture, sunset cruises, and more.

Admire architecture with Chicago’s First Lady

Around the world, Chicago is known for its outstanding architecture, and it’s easiest to admire the city’s legacy from the water. By partnering with the Chicago Architecture Center , Chicago’s First Lady offers the most comprehensive tour of the skyline — docents must train 100 hours before they can lead tours.

Speed across Lake Michigan on Seadog Boat Tours

Are you up for a thrill? Race across Lake Michigan on SeaDog Cruises, featuring 30 minutes of high speeds and exhilarating twists and turns. Come prepared to get splashed.

SeaDog also offers lakefront speedboat tours and a river/lake architecture tour, featuring views of Chicago’s iconic Buckingham Fountain, Grant Park, Museum Campus, and more.

Live it up on an Island Party Boat

Looking for a party? These tiki-themed boats are always a good time, offering drink packages, stellar views, and fun vibes. You can hop on an Island Party Boat at Monroe Harbor or the Chicago Riverwalk, which is also where you’ll find their beach-inspired bar Island Party Hut. Choose from a river cruise, lake cruise, tacky tour guide cruise, or even a dueling pianos cruise.

Go back in time with Chicago Fireboat Tours

Step onto a real, historic fireboat and get ready for a unique experience with Chicago Fireboat Tours . The river tours are given aboard a real piece of Chicago history — a retired fireboat that patrolled the Chicago from 1937 to 1981. Tours are led by expert docents and include historic and sunset options.

Splurge on a Free Spirit Yacht Cruises

Looking to splurge a little? These private yacht charters are the way to go. The spacious yachts comfortably fit up to 49 or 120 people, making them the perfect option for a large celebration or an intimate gathering. Premium bar and catering packages round out the experience.

Explore the Chicago River with Urban Kayaks

If you’re ready to ditch the captain and explore the water on your own, then it’s time to grab a paddle at Urban Kayaks . You’ll go through a brief training session before you hit the water, but you’re free to paddle the river or lake at your own pace. Or join in a guided tour to catch the sunset, fireworks, or historic highlights. Rentals are available at the Chicago Riverwalk or Monroe Harbor.

Rent an electric boat

Chicago Electric Boat Company offers fun and unique ways to get out on the water, including donut boats, retro boats, and even a bike boat that your group can pedal down the Chicago River. Rental locations include Marina City, the Chicago Riverwalk, and Rockwell on the River in Avondale.

See the skyline aboard Mercury Cruises

While Chicago’s summer fireworks are already fun to watch, it’s an entirely new experience when you’re on a 3D tour. Before the show, you’ll cruise around the lake and see some of Chicago’s famous landmarks.

Mercury Cruises also offer Urban Adventure, Canine Cruises, and Chicago by Night tours.

Check out Chinatown via Chicago Water Taxi

Hop on! The Chicago Water Taxi is a fun and cheap way to get around Chicago. The Water Taxi stops at Ogilvie Transportation Center, Chinatown, Goose Island, the Chicago Riverwalk, Michigan Avenue, and River North. Get a one-way ticket for $6 or an all-day pass for $10. Check their daily routes and schedules for more details. Cruises.

From this article

Tours & Attractions

Chicago architecture center.

Mercury, Chicago’s Skyline Cruiseline

Shoreline Sightseeing Company

Streeterville

Special Event Venues

Free spirit yacht cruises.

Urban Kayaks

River North

Wendella Tours & Cruises

The Magnificent Mile

Chicago’s First Lady Cruises

Related articles.

Articles , Itineraries , Parks & outdoors

Things to do in chicago in the spring.

What’s spring like in Chicago? Tulips bloom along iconic Michigan Avenue, cherry blossoms pop up in Jackson Park, and city parks begin to overflow with…

Holidays , Tours & attractions

Chicago ghost tours for halloween.

Chicago boasts a long and fascinating history — and that includes quite a few ghost stories. This Halloween, explore the city’s spooky side, from supernatural…

Articles , Bucket list

Things to do in chicago in the fall.

Chicago has something to offer every season of the year, but fall is particularly magical. The leaves turn golden in Millennium Park, a crisp breeze…

Food & drink , Tours & attractions

Chicago brewery tours and experiences.

Craft beer lovers flock to Chicago to get a taste of our dynamic brewing scene. A brewery tour can take you behind the scenes of…

Chicago craft brewery itineraries: Lincoln Park and Lakeview

These scenic waterfront neighborhoods are home to a historic zoo, popular shopping corridors, an iconic stadium, an amazing restaurant scene — and lots of great…

Chicago craft brewery itineraries: Downtown and South Loop

Historic architecture and world-renowned cultural institutions aren’t the only things that define downtown Chicago. The heart of the city, made up of the Loop and…

Chicago craft brewery itineraries: Wicker Park and Logan Square

One of Chicago’s hippest areas is also overflowing with beer options. This stretch of Milwaukee — which runs through Wicker Park and Logan Square —…

Chicago craft brewery itineraries: Pilsen and Bridgeport

There’s always something cool happening in Pilsen and Bridgeport on the southwest side. These distinct neighborhoods — from a vibrant, Hispanic enclave known for its…

Chicago craft brewery itineraries: Ravenswood Corridor

An industrial stretch of Chicago’s Ravenswood neighborhood has taken on a second life as one of Chicago’s most bustling brewing corridors. The area, which earned…

Explore hotels, flights, deals, and more

Plan your trip.

Chicago Newsletter

Stay in the know.

Visitors Guide

Start planning today.

Get the guide

Your Favorites

Quick access links.

See Today's Schedule

CHICAGO'S ORIGINAL ARCHITECTURE TOUR®

BEST SEAT IN THE HOUSE

Choose your adventure, chicago river architecture tour (90 minutes).

Take in the world-renowned architecture as our expert guides tell the story of 130 years of architectural innovation.

We like our drinks stiff, not our tour guides.

Chicago River Architecture Tour (45 minutes)

This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours.

The Ultimate Chicago experience.

We're In the People Business

This was one tour that I can honestly say was worth doing & probably should be a must do/ see on your visit to Chicago.

Ginette, 2023

We were recommended the architecture boat tour by a few locals and it was absolutely amazing!! Beautiful views from anywhere you sat and an extremely knowledgeable and funny tour guide led the trip. Great value for money and so so worth it. Thank you!!

Jessica W, 2024

The skyline was beautiful and the buildings all shined differently. Pictures come out amazing!

Christina, 2023

SEE FOR YOURSELF

Book your experience now.

7 things that might surprise you about the Chicago Architecture Boat Tour

T here are plenty of ways to take in the sights, sounds (and smells) of Chicago, but you don't necessarily have to be on land to do that.

And you don't have to be a tourist, either.

In fact, one of the most beloved ways — among locals and visitors alike — to experience city is by journeying across the Chicago River and Lake Michigan while a tour guide talks about buildings and regales you on the untold story of Mrs. O'Leary's cow.

In other words: a Chicago Architecture Boat Tour.

"As you're going up and down the Chicago River and on Lake Michigan, you're seeing the city’s evolving architecture, which is changing every year" said Andrew Sargis, director of sales and marketing for Wendella Tours and Cruises .

Wendella, billed as Chicago's "original" architecture tour, in 1935 gave its first architecture tour of the city from a wooden diesel yacht out on Navy Pier, Sargis said. Now, upwards of 20 architecture tours are offered daily, with more on the weekends. On average, Wendella tours see roughly 100,000 passengers each month over the summer, Sargis said.

And though the majority of guests on any given Wendella architecture tour are tourists, Sargis said, locals take them, too.

MORE: Even Chicagoans can't get enough of this tourist attraction: ‘It's about the only touristy thing I do'

"I was surprised when I first started, we get a lot of repeat locals," Bobby Scheffle, a Wendella tour guide told NBC Chicago. "And always there's a lot of local people that come on when they have guests visiting them in town. They like to show off the city this way."

But there's something else about the experience that makes it so very Chicago.

"I think it is really unique to experience the city from a boat on a river, because we think about other big cities in the United States -- there aren't many that have a river that go right through downtown," Scheffle said. "You feel like you're in the city, you hear the noise, and you see the buildings and all that."

Whether you're taking the ride for the first time or the 50th, bringing out-of-town guests out for a memorable activity or just itching to be a tourist in your own city, here are seven things to know about the Chicago Architecture Boat Tour.

Will weather stop a tour from running?

Wendella's architecture tours run year-round, Sargis said, although "weather is a factor."

Weather events like ice on the river or significant snowfall can impact operations, Sargis said, but they typically don't, since the Chicago River -- a federal waterway -- must remain navigable year-round.

While Wendella's boats do have climate-controlled indoor lounges, tours during the winter may run at limited times. But rain, snow, extreme heat or wind, unflappable Chicagoans still show up.

"We went on drizzly day a few years ago," Kathy Rambo wrote on NBC Chicago's Facebook page. "There were only about 10 of us on the boat!

And most often, the tour will run — rain or shine — so don't hesitate to bring a raincoat.

"I have certainly [given tours] under thunderstorms and downpours, and I've gotten drenched sometimes," Scheffle said. "I've never had a tour get canceled because no one bought a ticket. There's always someone wanting to come out here in the rain or the cold."

What's the best time of year (or day) to go?

It depends on when exactly your favorite time of the year is, and what you're hoping to see.

For Sargis, it's late summer. "There's this point of time in September when the weather is beautiful, but there's not that summer rush."

There are other times that Chicagoans may want to consider, too.

"St. Patrick's Day Celebration when they dye the river, and any Wednesday or Saturday night [over the summer], watching the fireworks over Lake Michigan , especially if you're local" Sargis said.

During the summer months, Wendella's tours run start as early as 9 a.m., with the day's final tour not ending until 10 p.m. or 11 p.m., Scheffle said, "so if you want to come for a ride to see the city lights, you can come late, and it's also beautiful, just a little more difficult to see the colors on the buildings if that's what you want to see."

Laura Pubins, who lives in a suburb outside of Chicago, agrees.

"My favorite one was when we were on a boat at sunset," Pubins wrote to NBC Chicago on Facebook. "It was an awesome new view of the city."

What's the most photogenic spot on the tour?

For Sargis, it's "anything out on Lake Michigan," with the skyline in the background.

On the river though, there's one moment that captures the city best, Scheffle said, no matter what time of day you're taking the trip.

"The best place to take a photo on the 90-minute river tour is when we come up the south branch from Chinatown," Scheffle said. "That's the best place because you get the whole skyline from the south. It's really beautiful."

For locals though, it may not be what you're looking at, so much as how you're looking at it.

"You're looking at [the city] from underneath," said Chicago resident Nick Pappas, 55, who recently found himself on a 90-minute river tour. "It's just a different perspective on the river that you don't get on the street level. As amazing as that sounds, you're only, like, 20 feet down, but it gives you a whole different perspective."

What does the training for a tour guide look like?

According to Sargis, all Wendella tour guides are trained in-house -- and the spots are competitive.

"There's high demand," Sargis said, of the position. "There are more people that want to be tour guides than space available. It's certainly a popular job, and people want to do it." While the tour guide of any given architecture tour isn't made public, many people do request certain ones for private events, Sargis said.

For the tours, there's a general script, with highlights that must be mentioned, Sargis said. But improvisation, along with sharing personal history is encouraged, too.

"All of the tour guides have their own experience in the city, and will add parts of their history in it," Sargis said. "We have a tour guide that is a retired police officer, and he will interject anecdotes form his career. We have a tour guide that's a Vietnam War Veteran, and when we go by the Vietnam War Memorial, he will always discuss the importance of it to him."

For Scheffle, the training included joining multiple tours a week for two weeks and flashcards.

"For a while, I, just drove Uber and Lyft," Scheffle said. "And then, I remembered that I really liked Chicago. I like learning fun facts about it. And there are people in the city that have that as a job -- to tell people fun facts about Chicago and I started looking into tourism jobs in the city."

What's the most common question tour guides get?

Believe it or not, it's not always about The Great Chicago Fire , or Mrs. O'Leary and her cow, at least on Scheffle's tours.

"My favorite thing on the tour that happens is probably when little kids ask questions," Scheffle said. "The common question that a kid will ask, because I talk about the tallest building, second tallest building, third tallest building, a lot of times a kid will ask what's the shortest building in Chicago? Which I don't have a good answer for."

Are you supposed to tip your guide?

"It's up to the discretion of the client," Sargis said. "I would say a lot of our passengers do tip our tour guides."

What's the absolute best part of the tour?

Sure the tour is photogenic, and the city's history is fascinating. And though some may go on the tour to find out what buildings are new, others prefer to think about the old.

"My favorite building to talk about is probably the Board of Trade building," Scheffle said. "Just because I remember walking by it much younger and always, I remember, really being impressed by it, thinking was such a cool big city building."

For a local on the tour, the memories are nice. But a day out on the water in Chicago is just hard to beat.

"It's great. I don't have to work," said Pappas, who has lived in the city for 55 years. "Every time, it's a little treat to go down the river."

Video editors Ivonne Ramirez and DS Shin produced and created the video for this story.

• Accessibility

Creepy Cruise

From mysterious sightings, creepy haunts, mobsters and more, you’ll hear stories of Chicago’s darker side on our newest nighttime tour. Cruise the Chicago River amidst twilight tales of the city you never knew existed… and might wish you could forget.

2024 CRUISING SEASON MAY 24 - OCTOBER 14

Tickets on sale now!

Bone-Chilling Chicago Awaits

Priority boarding now available!

• Includes exclusive early boarding period • Skip the queue during general boarding

Ticket Price

• Adults (Priority Boarding) $47
• Adults (General Boarding) $42
• Kids 5-15 (Priority Boarding) $24
• Kids 5-15 (General Boarding) $19
• Under 5 Free

Call us for group reservations at 312-332-1368 or contact us at [email protected] (group rates available Sunday - Friday).

Ticket Pricing

Full schedule.

May 24 - October 13 Departing Friday at 9:00pm & Saturday at 9:30pm

Located on Chicago’s Riverwalk

On the Chicago Riverwalk just off The Magnificent Mile

We love groups!

A fun, relaxing, informative boat tour along Chicago's beautiful waterways is the ultimate way to experience the city and leave a lasting impression on your group.

“Our tour guide really impressed us with how much she knew about the city. It wasn't a scripted speech. She truly loves her city and it showed! My daughter and I loved this tour and can't wait to do it again.”

Nicole C. Yelp, Chicago, IL

Frequently Asked Questions

No. Reservations are not necessary for daytime tours, though you are welcome to purchase tickets in advance online . We also encourage advance purchase online or dockside if you desire to cruise a particular date and time and want to guarantee your seats aboard.

We do advise that you buy CHICAGO BY NIGHT! and 3D Fireworks Cruise tickets in advance – online or at the box office – as these tickets are extremely popular.

Online we accept Visa and MasterCard. At our dockside ticket office, we accept cash, Visa and MasterCard.

Beverages – including water, soda, canned cocktails, beer, and wine – are available for purchase on board. Please note, no outside alcoholic beverages are allowed.

Snacks - including small items such as chips, cookies, and nuts - are also available for purchase.

Please note that all ticket sales are final.

All of our Urban Adventure Cruise, Chicago By Night! and 3D Fireworks tours pass through the Chicago River Lock System. Our guide/narrator gives a full explanation of the operation of the lock. You’ll feel the boat rise as you enter Lake Michigan and lower as you return to the River.

Yes. Our cruises depart rain or shine. We have open and covered seating on board.

Yes, of course! There are "Heads" located on board as well as one lined with newspapers for your dog(s) during the Canine Cruises.

The safety of our guests and crew is our number one priority. After more than 80 years providing memorable cruises of the Chicago River and Lake Michigan for millions of guests, we are proud to say we have a perfect safety record.

All of our vessels are regulated, licensed and inspected by the United States Coast Guard (USCG) every year, and have undergone stability testing to ensure our guests are safe on their waterway experience. Our captains and deckhands go through an extensive training and drilling program that goes above and beyond the standards set by the USCG. Because we are committed to continuing education, we provide extra training every day to our crew.

If you have any questions about our safety training protocols or other concerns, please contact our Company Security Office Captain Tom Hacker at [email protected].

No. Luggage is not allowed aboard the Mercury vessels. Please leave your luggage at your hotel or check your bags in at a hotel near the dock (be sure to confirm in advance the ability for the hotel to accommodate you). Also, please be aware that all bags (purses, backpacks, etc.) are checked before boarding.

Yes, strollers may be brought aboard and will be folded and stored in the indoor salon for the duration of the cruise. They are not allowed on the deck. Please note, children must be removed from strollers before boarding.

In accordance with ADA guidelines, we welcome service dogs onboard. The service animal must be harnessed, leashed, or tethered while in public places unless these devices interfere with the service animal's work or the person's disability prevents use of these devices. Emotional support animals, pets and other animals not covered by the ADA are not permitted. All dogs are welcome on  Mercury's Canine Cruise ! Please visit the ADA's FAQ on service animals for further details. 

We love groups and would be happy to offer you a group discount if you would wish to reserve in advance! Please call 312-332-1368 or [email protected] for more information! 

Please note that we do not offer group discounts for our 3D Fireworks Cruise, but are happy to make a group reservation for full price! 

Boarding begins 15 minutes prior to scheduled departure time. Choose any seat - all offer a great view!

Children under 5 are always welcome free of charge, but do still require a ticket. Folded strollers may be brought on board. Children’s rates available for kids 5-15 years old.

At this time the Riverwalk does not offer any elevators. For those who need ADA ramps, you may access the Riverwalk via the ADA ramp at State Street and Wacker Drive within the Vietnam Memorial Park. Then just follow the Riverwalk to the East under the Michigan Avenue Bridge. Our Ticket Office is marked with a blue awning. Our stairway offers handrails, and shade from the sun. For guests needing special vehicle drop-off assistance, click here for Mobility Assistance directions.

For safety reasons, motorized scooters and electric wheelchairs cannot be accommodated aboard the ship. Guests who can transfer may use the company's manual wheelchair, based upon availability. Please note guests using manual wheelchairs must be accompanied by individuals who are capable of assisting/lifting the wheelchair over the boat’s threshold. Under Federal law and due to special marine safety construction guidelines, USCG-regulated small vessels are not subject to land-based architectural configuration requirements. Although we do our best to accommodate passengers with limited mobility consistent with our vessel capabilities, staffing and the docking space which is publicly owned and controlled, we can do a better job with advance notice .

LAZ Parking Garage at 111 E. Wacker Drive. This garage is across the street from our street-level dock entrance. Make a self-parking reservation online .

Discount rates available for Mercury customers with validation: $14 for 1-3 hours or $15 for 3-4 hours of parking. After 4 hours, standard rates apply. IMPORTANT: You must have your parking ticket stamped at our ticket window or on your boat in order to receive the discounted rate. Stamped tickets must be further validated at the parking garage office before departing the garage. Note: LAZ Parking Services at 111 E. Wacker is not owned or affiliated with Chicago’s First Lady Cruises. The parking information posted here is merely for the convenience of our guests and is not to be construed as a recommendation or endorsement.

We are located on Michigan Avenue just 3 blocks north of Millennium Park. Visit TheMagnificentMile.com or MillenniumPark.org for activities, events and special offers.

• Entertainment
• Rex Reed Reviews
• Awards Shows
• Climate Change
• Restaurants
• Gift Guides
• Business of Art
• Nightlife & Dining
• About Observer
• Advertise With Us

The Best Weekend Escapes from Chicago

Whether your idea of unwinding involves wine tasting, hopping onto a boat, wandering antique stores or strolling art galleries, we’ve got you covered.

While there’s plenty to do in Chicago , sometimes you need a weekend away from the hustle and bustle. Whether your idea of unwinding involves wine tasting, hopping onto a boat, wandering antique stores or strolling art galleries, there are plenty of getaways surrounding Chicago where you can do just that—and they’re all within a five-hour drive. Blessed with the Great Lakes and many smaller, inland lakes, as well as rivers, chances are you will wake up by the water.

Getting away from the city, however, doesn’t mean losing access to culture. In fact, many of these small towns near Chicago thrive on fine dining, art and natural parks that will make you want to whip out your phone to capture the striking images. Be sure to pack hiking boots, too, to explore gorgeous trails, and sandals to walk on the beach or stroll around town. That this part of the Midwest isn’t super spread out also means you don’t need to drive very far for a weekend escape, which translates to spending less time in the car and more time enjoying your vacation.

Here are five destinations to check out, ensuring you come back to the city relaxed and reinvigorated. If a road trip is calling and you’re not sure where to go, this cheat sheet will help.

Lake Geneva, Wisconsin

1.5-Hour Drive

Architecture geeks and The Gilded Age fans will love the grand, historic estates dating back to the late 1800s and early 1900s that surround Geneva Lake, accessible via a stroll around a section of the 26-mile Lake Shore Path or aboard a narrated Geneva Cruise Line boat tour . Dine with a lake view on the patio at Barrique Bistro & Wine Bar or linger over Italian-American food like wild-boar Bolognese pasta at Sopra Bistro on Main Street. Shop downtown for cheese curds and cheddars flavored with whiskey, dill and more at Hill Valley Dairy’s storefront , and poke into the Lake Geneva Public Library , designed by Frank Lloyd Wright protégé James Dresser and featuring stained-glass windows from Wright’s now-demolished Lake Geneva Hotel. For whimsical décor finds and entertaining frills, head to the other side of the lake to Fontana Home . The best design-oriented spot for a beer is at Topsy Turvy Brewery , within a 1910 former church.

Where to Stay

Featuring an outdoor pool with striped umbrellas and a speakeasy-style bar, Maxwell Mansion ’s 28 rooms are divided between the main house and former horse stables. For a full-service experience that includes a spa, steakhouse, Italian restaurant and outdoor pool, try the  Grand Geneva Resort & Spa , whose interconnected buildings were once home to the Playboy Club. Today, you can sip cocktails in the lobby’s sunken lounge.

Saugatuck, Michigan

2.5-Hour Drive

Hugging Lake Michigan’s western shoreline, Saugatuck, fittingly known as “The Art Coast,” is home to dozens of galleries. Most are sprinkled downtown near shops and restaurants, although the two-story, 12,000-square-foot J. Petter Galleries just outside of town is worth a trip, and hosts a wine bar within. In nearby Douglas, one of the nation’s oldest artist residencies— Ox-Bow , affiliated with the School of the Art Institute of Chicago, also a destination for art and writing classes—hosts an art gallery and boutique (Ox-Bow House) in an adorable white church dating back 152 years. Modales Wines in Fennville pours wines crafted by its Napa Valley-born winemaker, formerly of Duckhorn. Explore further on a vertical hike down sand dunes at Opal Beach, or rent a 1950s electric boat from Retro Boat Rentals to cruise along the Kalamazoo River to live our your IRL Emily Henry novel dreams.

Owned by Chicago design firm Soucie Horner , the 11-room Wickwood Inn  is a new, modern revamp of The Silver Palate Cookbook author Julee Rosso ’s inn. Rosso also owned a gourmet-foods shop of the same name in New York City. Antiques and artwork tie into a clear coastal vibe that includes outdoor s’mores and French bistro chairs on the patio.

Kohler, Wisconsin

This company village town—nearly everyone works for the luxury plumbing manufacturer—also excels at hospitality. The Immigrant Restaurant has long been considered one of Wisconsin’s best fine-dining restaurants; it embraces early-American art and décor while serving a five-course tasting menu, plus delicacies like caviar and 16 artisan Wisconsin cheeses. At the three-level, 36,000-square-foot Kohler Design Center , rooms by celebrity designers can be toured and the design staff is available to chat. Then, at Kohler Waters Spa, hydrotherapy treatments incorporate Kohler’s Vichy shower. On your way into town, swing by Art Preserve , a museum dedicated to artist-built environments by folk artists. Tours of the Kohler factory across the street from the hotel are led by retired employees.

The American Club is the most luxurious of the three Kohler properties, with 241 rooms. Built in 1918 for single male immigrant employees, it’s now one of Wisconsin’s most coveted properties, with a spa, yoga studio, multiple restaurants, golf courses and shops all within a short walk and managed by the resort.

Galena, Illinois

3-Hour Drive

Situated along the Mississippi River, Galena boasts an adorable downtown dotted with antiques stores (like the 200-some vendors at Elizabeth’s Grand Antique Co. in a former school) and unique boutiques along Main Street. That includes Galena Apothecary (formerly of Chicago, the owner opened the shop in her favorite weekend-getaway town), Galena Book & Paper (books and stationery) and Galena River Goods (candles, skincare products, barware and clothing). Sip bubbles in Champagne on Main ’s outdoor courtyard and choose your dinner spot after a walking tour with Galena Foodie Adventures , visiting five different eateries.

Tuck in at night at Goldmoor Inn , a castle-like structure just outside of town with 13 suites and breakfast included. Massages are also available on-site, in the inn’s dedicated spa room, including a hot-stone massage to work out the kinks.

Traverse City, Michigan

5-Hour Drive

This emerging wine region is also a great spot to hike; make sure to take in the soaring bluffs at Sleeping Bear Dunes National Lakeshore and to sail. The Wind Dancer , offers sunset sails nearly daily as well as Champagne Sails on Sunday afternoons. Short on time but still want to experience a local winery? Head to the 155-acre Brys Estate Vineyard & Winery , where the vineyard views from an elevated deck are nothing short of picturesque, with vistas of a lavender field and gardens blooming with flowers and herbs. The winery also serves frosé, plus cheese and charcuterie boards. Perusing downtown Traverse City’s shops, including two bookstores, can easily fill an afternoon. History buffs will love Trattoria Stella ’s cave-like environment, located at The Village at Grand Traverse Commons , a former state-run mental hospital with a philosophy that a beautiful environment is healing.

 Delamar Traverse City ’s perch above the West Arm of Grand Traverse Bay means water views for days and the on-site yoga studio puts wellness within easy reach, plus a restaurant wildly popular with locals. Or, wake up next to the grapes at the 10-room Inn at Black Star Farms , which also hosts private yoga classes in its vineyard.

We noticed you're using an ad blocker.

We get it: you like to have control of your own internet experience. But advertising revenue helps support our journalism. To read our full stories, please turn off your ad blocker. We'd really appreciate it.

How Do I Whitelist Observer?

Below are steps you can take in order to whitelist Observer.com on your browser:

For Adblock:

Click the AdBlock button on your browser and select Don't run on pages on this domain .

For Adblock Plus on Google Chrome:

Click the AdBlock Plus button on your browser and select Enabled on this site.

For Adblock Plus on Firefox:

Click the AdBlock Plus button on your browser and select Disable on Observer.com.