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Learn how to easily plan your dream trip to Florida!

3 Days in Key West: An Epic Weekend In Key West Itinerary

February 24, 2022 //  by  Florida Trippers

Are you looking for the perfect weekend in Key West? If so we have put together a three-day itinerary for your weekend in Key West! We have put together the best things to do in Key West . Your weekend in the Keys will be spent enjoying history, restaurants, state and National parks, beaches, nightlife, and more. We have crafted a plethora of tours to enjoy on your weekend trip to Key West!

Planning your trip to Key West last minute?

Make sure to book ahead! Hotels and tours often sell out the closer you get to your trip. Here are our top picks for Key West!

Top Experiences And Tours In Key West:

• Dolphin Watching And Snorkeling Eco Tour (Top pick!)
• Schooner Sunset Sail (2 hours)
• Reef Snorkel From Key West (Includes breakfast and mimosas)
• Hop-On Hop-Off Trolley Tour (Great way to see the city)

Top Places To Stay In Key West:

• Margaritaville Beach House Key West (Modern mid-range)
• Blue Marlin Motel (Affordable in downtown)
• Hampton Inn Key West (Waterfront with pool)
• Wicker Guesthouse (Great location!)

The first day of your Key West Itinerary will be spent exploring all the historical sites in Key West, the second day will take you to Dry Tortugas National park or Bahia Honda State Park and Day three will be spent exploring a corral, a food tour and shopping.

Before you plan your trip, make sure to check out The Best Times To Visit The Keys where we break down each month and talk all things weather!

Getting To Key West

Getting to a Key West weekend getaway is very easy! You can arrive by car, plane or boat.

If arriving by plane, the closest large international airport is Miami (MIA). Located just about a 3 hour drive north. If you do not want to rent a car, there is a shuttle bus from both FLL and MIA airport to Key West. However, you can also fly into Key West airport!

If driving you have the opportunity to stop along your drive through the Florida Keys. Located about 160 miles south of Miami, why not explore the upper and middle keys on your way to your weekend getaway in Key West.

For those coming from Fort Myers or Marco Beach areas, you can take the Key West Express ferry. The journey is 3.5 hours.

Getting Around During Your Key West Weekend Trip

We HIGHLY recommend renting electric bikes to explore during your weekend trip to Key West. It is such a fun way to explore with the fresh ocean breeze on your Key West weekend getaway. Another fun way to see the city is on a bike tour complete with a slice of Key Lime pie after biking all day!

You can use your own car if driving or rent a car at the airport. This is a great option if you want to explore the upper and middle Keys on a long weekend in key west.

Uber is easy to find here, and the hotels have shuttles. Key West is also a very walkable city, and you explore the downtown area on foot. Or try the hop on the hop-off trolley that operates through the city. You can book a tour here !

Are you a history buff? On the first day of your Key West weekend itinerary, we suggest exploring the historic sites across downtown Key West. Explore the home of a great American author or the winter getaways of former U.S. Presidents!

After a full day exploring and learning the history, it will be time to let loose on your weekend in Key West! Head on one of the amazing sunset cruises around the harbor or stay on land and enjoy a pub crawl across Duval street!

Stop 1 : Breakfast in Mallory Square

Located on the water in the Old Town, Mallory Square is the center of Key West. The Square has shops and restaurants that the whole family can enjoy! Why not start your day with breakfast here! We suggest breakfast at Cuban Coffee Queen.

Choose a hearty Key West-style breakfast or a Cuban breakfast to start fueling your body before spending the day exploring Key West!

After breakfast explore Mallory Square where street vendors and performers are often present.

Stop 2 : Harry S. Truman’s Little White House

Built in the 1890s, Harry Truman’s Little White House is Florida’s only presidential museum and is one of the best places to learn about American history.

Named after Harry Truman as he used this home as a winter getaway from DC. He use the house from 1946 through 1952. Presidents Taft, Eisenhower, Kennedy, Carter, and Clinton have all visited as well.

The entrance is $20 per adult or $10 per child. Included is a tour of the home and grounds where visitors can see how presidents lived while on their weekend in Key West!

Stop 3: Ernest Hemingway House

The next stop on your Key West itinerary is the Ernest Hemingway House . Located just a block from Duval street, the Hemingway House is a Spanish Colonial-style mansion. It is full of the famous writer’s personal items, historic furnishings, photographs, paintings, and more.

This is a must-see Key West destination for anyone who loves history, architecture, or literature! Worth noting the grounds are filled with the famous six-toe cats that are descendants of cats that roamed the grounds while Hemingway himself lived in the house!

Stop 4 – Sunset Cruise

Whether you are in town for a Key West couples getaway , a Key West girlfriend getaway, or a Key West bachelorette party we have the perfect way to end your first day! Why not end your first day with a Sunset Cruise with Buffet Dinner and Open Bar! There is truly nothing like being out on the calm and peaceful ocean while watching a gorgeous sunset.

On this two-hour cruise around the harbor, you will be fed a delicious dinner with favorites including pulled pork in mojo sauce, black beans, and rice, fish, mixed vegetables, pasta with mini shrimp, and more. You can dance on the upper deck, or sip a cocktail and watch the sunset!

For those looking for something a little more relaxing why not hop aboard the 2-Hour Sunset Sail on Schooner America 2.0 tour with two viewing decks and the calmness of open water.

Optional: Stop 5 -Pub Crawl

If you would rather stay on land, to end your first night on your weekend trip to the Florida Keys try a Duval Street Pub Crawl! Key West is known for its nightlife on Duval street, so why not let a tour guide you into the hottest spots in town with your admission and a cocktail at each stop included!

For those looking for a fun night out why not book this Drag Queen Guided tour that takes you to the most happening nighttime destinations in Key West! Featuring drinks, karaoke sing-alongs, dancing, and all the drama that comes along with being in the presence of a world-famous drag performer!

Make sure to check out the best bars and nightlife in Key West!

On Day 2 of your weekend in key west, we suggest heading on a day trip to Dry Tortugas! You can either do a half-day seaplane tour or a full-day boat tour! Check out our guide to avoid the big mistakes plus tips when visiting Dry Tortugas National Park !

After your trip to one of the best and hardest to reach National Parks, why not relax downtown and grab dinner and drinks on the water! You can pack and lunch even an alcoholic beverage to enjoy while on the island!

If getting to the Dry Tortugas is not an option on your trip, why take a day trip to Bahia Honda State Park!

Stop 1 : Dry Tortugas Day Trip

Dry Tortugas is a 100-square mile park made up of seven small islands and is located just about 80 miles from Key West. This tropical paradise is also home to the well-known and magnificent Fort Jefferson. A visit here mixes nature, history, and transports visitors to a remote place!

The only way to visit here is by private or chartered boat tour , chartered seaplane tour, or the Yankee Freedom Ferry . Reservations for the ferry fill up very quickly, so you’ll need to plan several months in advance. It is worth noting that the visit to Dry Tortugas can cost several hundred dollars and needs to be booked in advance. But it is 100% worth it!

For those who are adventurous enough, why not spend the night for some primitive camping in Florida !

Stop 2 : Visit Fort Jefferson

Most of the iconic photos you see from the Dry Tortugas is the red brick, Fort Jefferson. Take a tour of Fort Jefferson to learn about the island chain’s historical past as a prison. It once housed nearly 2000 inmates. You can also take a self-guided tour as well with numerous plaques spread across the fort. Make sure to put this on your list when doing a Florida Keys Road Trip!

Stop 3: Snorkling

No weekend in Key West is complete without a trip to Dry Tortugas. It is a great spot for snorkeling and scuba diving around the National Park. Less than 1% of the National Park is on dry ground, making the Dry Tortugas an underwater paradise!

With crystal clear water, gorgeous coral some rising 50ft high, it is truly spectacular! There are fish species here that don’t exist anywhere else in the world. Keep an eye out for  sea turtles as the island is named after the Spanish word for turtles!

The popular spots to go, scuba dive, include the Maze, the Bat Caves, Dante’s Inferno, Texas Rock, and the Windjammer Wreck one of the most beautiful shipwrecks in the world.

Optional: Bahia Honda State Park

For those who don’t have the time or budget for Dry Tortugas, head to Bahia Honda State Park . We have an entire guide on what to explore here!

Known for its iconic Florida Key scenery, sandy beaches, clear waters Bahia Honda State Park is the best place to visit on a weekend in Key West. Just under 40 miles from Key West, it only costs $8 per vehicle to visit!

You will want to arrive early on weekends or holidays as once capacity is hit, the park will close!

Make sure to check out some of our other favorite things to do in the Lower Keys in addition to Bahia Honda or check out our list of the Best Florida Keys Beaches for some more ideas of places to visit!

Stop 4: Dinner at Blue Heaven

You are sure to have worked up an appetite after exploring Dry Tortugas! We suggest heading to one of the best restaurants in Key West for dinner.

Head to the historic Bahama Village where you can enjoy the island flavors. From the fresh snapper in the yellow submarine sandwich to popular Caribbean “BBQ” shrimp or a vegan and vegetarian option, there are plenty of options!

Stop 5: Ghost Tour

After you return from your half-day trip to Dry Tortugas or Bahia Honda, why not spend your evening on a ghost tour of Key West! The best part is you will be transported by trolly along with the spooky and haunted sites across the island.

On day 3 of your weekend in Key West itinerary, you will be taking it easy after a jam-packed first two days and nights! You will start with an amazing boozy brunch spot, followed by either snorkeling the reef, taking food out, or purchasing handmade leather sandals!

Stop 1: Brunch at Bagatella

Bagatelle serves a breakfast hangover happy hour from 9 to 11:30 a.m. every morning. If you had a late night during your Key West bachelorette party head here, where you can enjoy fun alcoholic beverages with scrumptious brunch plates. Dive into a crab cake benedict, crispy fried French toast, or braised pork sandwich with pineapple slaw.

Stop 2 : Snorkeling and Breakfast

On stop 2 of your Key West getaway itinerary why not take a Key West: Reef Snorkel Morning Tour with Breakfast & Mimosas! This tour is 3 hours where you will visit the third longest reef in the world, snorkel, and enjoy a delicious breakfast accompanied by mimosas on your trip back to port!

Stop 3: Optional : Key West Food Tour

Next up, for those who want to stay on land is a Southernmost Food and Cultural Wal k ing Tour ! On this 5 stop tour, you will get to taste some of the most famous foods of Key West. Think conch fritters, fresh fish tacos, and the amazing key lime pie! Head to hole-in-the-wall places you would never find on your own!

Stop 4: Smather’s Beach

On your 3 days in Key West, you must visit one of the beaches. With half a mile of soft sand, Smathers Beach is the one to go to if you like lively, fun-filled beaches.

Smathers is a great beach with something for everyone like swimming, snorkeling, kayaking, parasailing, sunbathing, and beach volleyball. Plus there are food vendors and beautiful palm trees shoreline perfect for picnicking under!

Stop 5: Kino Sandal Factory

Since 1966, the Kino Factory has been a staple of any Key West weekend trip! Stop in the purchase handmade leather sandals that are hand-cut and produced on-site in this traditional sandal factory! Choose from over 17 styles with various color combinations for men, women, and children. 

Where To Stay In Key West

There are plenty of options if looking for places to stay in Key West ! From hotels, home rentals , camping , and more!

Make sure to check out our list of the Best Resorts In The Florida Keys ! There are some really epic resorts featured for couples, families, and more.

The Saint Hotel Key West, Autograph Collection

If you are looking to be in the heart of the action, The Saint is located just 4 minutes from Duval Street. This upscale hotel is also close to Ernest Hemingway and Smathers Beach. While the rooms are small, they are well-appointed and bright and airy, or splurge for a much larger suite!

Amenities include a restaurant and bar on-site as well as a chic outdoor pool with a waterfall and Dj on the weekends.

Check Rates: Booking.com

Key West Marriott Beachside

On our most recent trip to Key West, we stayed at the Key West Marriott Beachside. Located on 7 prime acres with oceanfront access with the pool as the centerpiece of the resort. This is truly one of the Best Places To Stay in The Florida Keys!

From the hotel’s marina, you can rent jet skis, kayaks, and paddleboards. There is a complimentary hotel shuttle downtown multiple times daily. Many of the balconies are oceanfront allowing you to relax and enjoy a sunset or ocean breeze from your town room!

If you have a car parking is $25 a night!

Dog-Friendly Home With Private Pool

Are you planning an extended weekend in Key West and want to bring your pups with you? This  Dog-Friendly Home With Private Pool  is the place to stay!

Located in Central Key West, you are in a prime location for exploring shops, restaurants, beaches, historic landmarks, and dog parks! The home is ready to accommodate up to 3 guests with 2 bedrooms, 2 beds, and 1 bath.

>>>Check Rates:  VRBO.com

Waterfront Oasis 

This 2 bedroom 2 bath home has amazing views of the ocean. This property  can sleep 6 people in 4 beds. This is truly one of the Best Places To Stay In Key West!

The property features plenty of outdoor seating, a grill, and a pool table. The home comes with life jackets and kayaks so that you can explore the channel that the house sits on.

Where to Eat During Your 3 days in Key West

Latitudes is one of the classiest restaurants in Key West. To reach it you’ll have to hop on a free ferry because Latitudes is on an island of its own!

With waterfront seating, delicious food, and excellent service, it’s open for breakfast, lunch, and dinner. For breakfast, savor the lobster benedict. For lunch, try the surf & turf burger. And for dinner, twirl up the Key West pink shrimp carbonara or cut into the lemon glazed yellowtail snapper.

Banana Café

This French-inspired restaurant serves up some of the best crepes in town. Enjoy them for breakfast, lunch, or dinner.

Try everything from the breakfast-themed la super crepe to the seafood-filled la Mahi piccata crepe to the popular homemade key lime pie crepe. At lunch, be a little adventurous and try the baked escargot. Or for dinner enjoy the half roasted duck, seafood risotto, and French country chicken. There are also a good number of vegetarian options available at Banana Café.

Hogfish Bar & Grill

Situated on Stock Island just 15 minutes from Key West, is Hogfish Bar and Grill. Known for its fresh seafood and oceanfront location, it is frequented by Florida Keys locals.

The hogfish tacos and hogfish sandwich – named after both the fish and the restaurant – are two of the most popular items on the menu. There is live music on the weekends.

Those looking for vegan and vegetarian options will want to head to The Cafe. Breakfast is served every Monday through Friday until noon. If a dish on the menu doesn’t fit your dietary habits, then simply ask your server for the vegetarian or vegan version.

On Saturday and Sunday, mornings switch to brunch service! We love the Polenta Cake Benedict with lemon-caper hollandaise. You can’t go wrong with the Caprese Egg Sandwich with house basil pesto, garlic spinach, grilled tomatoes, and fresh mozzarella.

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Florida stories: a walking tour of key west.

Tom Scherberger                                                                

Want to explore the cultural, historical, and architectural treasures of Key West, Fla.? There’s an app for that.

Just go to Florida Stories Walking Tours , and download the app created by the Florida Humanities Council .

With this app you can learn, at your own pace and on your own schedule, what some of Florida’s most unique towns and cities have to offer.

Here’s an overview of what you can experience via the Key West app:

Where : Old Town Key West Historic District Number of stops : 12 Total time : 90 minutes Author : Bruce Neff, Key West historian and executive director of Historic Markers Inc. Start : The Custom House

The Margaritaville vibe that lures more than 3 million visitors a year to Key West is built on a colorful history of shipwreck scavengers, boat captains, literary luminaries and adventurers that you’ll discover on this fascinating and compact walking tour.

The island city, with the Atlantic to the east and the Gulf of Mexico to the West, has maintained its distinctive tropical charm through hurricanes, yellow fever outbreaks, and T-shirt shops.

Key West has the largest historic district of frame buildings in the United States and its architectural style is unique.

Clinton Square , featuring a granite monument honoring Yankee troops surrounded by a fence honoring Confederates, is the only joint memorial of its kind in the country and a reminder that this was the only Southern city occupied by the Union for the entire length of the Civil War.

Old Custom House is the original, more modest building that was moved to this spot after the grander structure at stop 1 was built, reflecting the federal government’s attempts to regulate the wild and lucrative shipwreck industry that made Key West what it is.

Sloppy Joe’s Bar is inextricably linked with Key West’s most famous resident writer, Ernest Hemingway, and a band of colorful characters; it remains an authentic slice of Old Town.

The Porter House is not only a great example of classic Key West architecture, but the backdrop of the fight against crippling yellow fever epidemics that once threatened the tropical city.

The Oldest House and its gardens, complete with a detached kitchen, is a microcosm of the city’s history.

In the early 1800s Key West was the richest city per capita in the country and the biggest Florida city until the early 20th Century.

Things to Do

More than 3 million visitors are drawn each year to America’s Southern-most city, and there’s no shortage of ways to while away your time. There’s plenty more history to be had -- the Hemingway House (and its six-toed cats), the Truman Little White House (also used by five other presidents), and Fort Zachary Taylor State Park (a Civil War fort with a beach for swimming and snorkeling).

Get a broader view of the city with a narrated hop-on, hop-off trolley tour .

Sports fishing options span deep sea charters to light tackle back-country excursions.

Don’t miss sunset at Mallory Square , a veritable carnival of street performers (sword juggling and trained cats anyone?)

Dining options are vast, from fine to funky. Try the outdoor Blue Heaven , where chickens roam as diners tuck into classic Key Lime Pie. The modest El Siboney provides a taste of Havana just 90 miles south. Florida’s most famous chef, Norman Van Aken, calls Nine One Five “one of the nicer places for dinner” on Duval Street.

And while there are plenty of places for adult beverages, nothing beats the Gulf of Mexico view from the upper deck bar of Louie’s Backyard .

PLACES TO REMEMBER

Florida Keys

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Catamaran Cruises in Key West, FL

Escape the downtown crowd - cruise with billy.

Key West’s nautical history is all based on its proximity to the world’s 3rd largest living coral reef. From pirates and privateers to ship wreckers and fisherman the draw has always been the sanctuary provided by the Florida Great Barrier Reef.  Key West’s coral rock islands trace a contiguous pathway from the Atlantic Ocean & Gulf of Mexico intersect all the way to mainland Florida. To this day our primary industry, tourism, celebrates our unique natural ecosystem in the shadow of the reef. 

Whether you want to cruise a couple of hours, island-hop all day, or see our beautiful wildlife, Billy has you covered! Bring your reef-safe sunscreen, and we’ll take care of the rest!

Ticketed Tours

• Kid Friendly!
• Users All ages
• Info Up to 36 people
• Clock 3.5 hours

Dolphin Watch & Snorkel Tour

Search for wild dolphins in their natural habitat and snorkel Key West’s backcountry waters off the Seabreeze!

• Most Popular Cruise
• Info Up To 38 People
• Clock 2 hours

Key West Sushi & Sunset Cruise

Dine on fresh sushi while taking in the famous Key West sunset. You will cruise past the southernmost point of the U.S., tropical beaches and a Civil War era Fort Zachary Taylor Historic Sate Park.

Private Experiences

• Our Newest Boat
• Info 1-6 People
• Clock 2 to 8 hours

Barefoot Private Charters

Create the perfect outing for up to 6 with a custom charter! Cast off from the island and explore the unique nature surrounding the Florida Keys!

• Info 1 to 40 people
• Clock 3 Hours

Morning Island Charter

Spend your morning at the sandbar and experience the turquoise waters surrounding Key West at a slower pace on this private charter.

• Clock Varies

Seabreeze Charters

Snorkel, see Dolphin, or visit a sandbar with an open-air cruise for up to 40 people. Create the perfect escape with a private adventure aboard our 45-foot Corinthian catamaran!

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CONCH TOUR TRAIN

SEE THE BEST OF KEY WEST ON THE TOUR THAT’S BEEN ENTERTAINING GUESTS SINCE 1958

TICKETS & PACKAGES

Buy online & save, 1-day conch tour train.

• 1-day tour of the Conch Republic
• One full loop through Old Town Key West
• Includes three stops
• FREE Two Guided Walking Tours included
• FREE admission to the Sails to Rails Museum included
• FREE coupons worth up to $50 in discounts
• Open-air sightseeing perfect for taking pictures

2-Day Conch Tour Train

• 2-day tour of the Conch Republic

Conch Train and Ghosts & Gravestones Package

• Conch Tour Train:
• Ghosts & Gravestones Night Tour:
• Explore Some of Key West’s Most Haunted Sites…
• 1 stop at the Key West Shipwreck Treasure Museum

ONE OF THE MOST POPULAR KEY WEST ATTRACTIONS

The world famous conch tour train in key west.

All aboard and welcome to 400 years of history, family fun and excitement! The Conch Train is one of Florida’s most popular attractions and for good reason. Our expert ‘engineers’ and friendly staff have delighted over 15 million guests with legends such as Ernest Hemingway and lores of this charming tropical paradise. Your tour of Key West will give you a conch’s eye view of all the wonderful Key West attractions. No Key West vacation is complete without The World Famous Conch Tour Train.

100% SATISFACTION GUARANTEE

• FREE admission to the Sails to Rails Museum is included with ticket.
• Full-color map and discount coupons for Key West attractions, restaurants, and shopping with every ticket.
• Stops at Truval Village: Steps away from the Ernest Hemingway Home and Museum, the Key West Lighthouse, the Southernmost Point, and Key West Butterfly and Nature Conservatory.
• Rated 4.5 stars on Google

279 reviews

Conch Tour Train 4.3

HOW OUR TOUR WORKS

An amazing 75 minute adventure.

This Key West tour begins at the 303 Front Street Depot and ends right behind it in Mallory Square. Once you have your ticket, climb on board and take your seat, as you are about to embark on a terrific 75-minute journey through time. During the tour, the train will make one loop through Old Town Key West.

How Our Tour Works

Enjoy 3 stops.

First Stop (B): Stop B is at Truval Village , corner of Duval St. and Truman Ave. From Truval Village you are just minutes away from the Ernest Hemingway Home and Museum, the Key West Lighthouse, the Southernmost Point, the Key West Butterfly and Nature Conservatory and the many fine art galleries, shops and restaurants of upper Duval Street.

Second Stop (C): The second stop is at Station Depot , corner of Front St. and Duval St., allowing for a 10-minute rest break where you will find refreshments and shopping.

Third Stop (D): The third stop is at the Sails to Rails Museum  (Flagler Station), corner of Caroline St. and Margaret St. This stop is also where those who wish to can disembark to see the sights of the Historic Key West Seaport and choose to catch a later train.

Where to board the Conch Tour Train

The best place to board the train is at Front Street; you may also board at Truval Village or Sails to Rails Museum if there are still seats available. If you are closest to the Roosevelt Depot, you can take advantage of our complimentary transportation down to the Station Depot. It takes approximately an hour to get to Mallory Square where you will then board a train.

Boarding every 30 minutes

9:00 AM - 4:30 PM

• First tour starts at 9:00 am.
• The last tour departs from Front Street at 4:30 pm.
• Closed the last Saturday in October (Fantasy Fest).
• All schedules are subject to change. Please call (305) 707-5775 for the most current information.

Key West Attractions

Points of Interest

Since 1958, the Conch Tour Train has treated guests to a close-up view of the Southernmost City’s most popular places including Mallory Square, Sails to Rails Museum, the Key West Aquarium and more.

TRAVEL GUIDE

Things to do with Kids

Mallory Square

Featured Attractions

What are the must-see places in key west.

• Duval Street: The street is lined with perfectly preserved 19th-century buildings that have now been lovingly restored and repurposed. From the local boutiques to the charming cafes and top-rated restaurants, Duval Street is filled with something for everyone..
• Mallory Square: No trip to Key West is complete without experiencing the famous Mallory Square Sunset Celebration. Every evening, locals and tourists gather to watch the sunset over the Gulf of Mexico. You can enjoy live music, street performers, and food vendors while taking in the breathtaking views. It’s a great way to end a day of exploring and relaxing with friends and family.
• Truman Little White House Museum: Visit the winter residence of President Harry Truman and get a glimpse into his life on the island. You can explore the house’s historic rooms, including the office where the president spent his time and you’ll find a gallery filled with photos and memorabilia of Truman’s presidency. The museum has knowledgeable guides that can take you through the house and provide you with fascinating insights.
• Key West Aquarium: Home to a wide variety of marine life, the Key West Aquarium is a must-visit attraction that’s fun for all ages. You can see sharks, sea turtles, stingrays, and other fascinating creatures up close. Don’t miss the interactive touch tanks where you can hold a starfish or sea urchin. The aquarium is committed to marine conservation and education, so you’ll not only have fun but also learn about the issues affecting our oceans.
• Key West Shipwreck Museum: Discover the dangers and adventures of shipwreck salvage in the 1800s at the Key West Shipwreck Museum. You’ll learn about the island’s unique maritime culture and see artifacts from shipwrecks around the world. Check out the lookout tower for a panoramic view of the surrounding area and a chance to ring the lookout bell. 
• Sails To Rails Museum: Explore the history of the railroad, the story of Henry Flagler, and his ambitious project to connect Key West to the mainland via the Overseas Railroad. You’ll see vintage railcars, historic photographs, and learn about the train’s construction and destruction in the 1935 Labor Day hurricane. 

Enjoy visiting Key West as the Conch Tour train journey takes you through the city’s historic streets, beautiful architecture, and breathtaking sights. The knowledgeable guides will offer interesting insights into the city’s history and culture, pointing out the most architecturally inspiring buildings.

How many days do I need to visit Key West?

Whether you have one day or several to visit Key West, there is a fantastic way to see Key West in one day by taking the Conch Tour Train. There are several popular attractions and activities that you won’t want to miss, including exploring the historic Old Town, visiting the Ernest Hemingway Home and Museum, and experiencing the legendary sunset at Mallory Square. Make sure you see it all by hopping on one of our Conch Tour Trains. It’s a fun and convenient way to see the most popular sights, and you can customize your journey to fit your preferences.

How can I explore Key West without a car?

Yes! The city is incredibly walk-friendly, boasting numerous sidewalks and pedestrian-friendly streets. For an immersive experience, you can hop on a Conch Tour Train tour, which delves into the history and culture of Old Town Key West. With knowledgeable guides and picturesque scenery, this train journey takes you through the charming Old Town, passing by delightful houses and enchanting landscapes. The tour gets you close to all major highlights, including the renowned Ernest Hemingway Home and Museum, the fascinating Key West Aquarium, the famous Mallory Square, and the adventures in the Key West Shipwreck Museum.

Where is Mallory Square?

Mallory Square is most famous for its sunset celebration. It has become synonymous with Key West and draws more than a million tourists and locals every year. Every evening, hundreds of tourists gather here to experience the vibrant culture of Key West and watch the beautiful sunset. During the sunset celebration, visitors can enjoy live music, street performers, and food vendors offering tasty local cuisine.

What is the Sunset Celebration in Key West?

The Sunset Celebration is a daily event that has become a staple of the island’s culture and a must-see for any traveler. It all started with a group of local street performers who would gather at Mallory Square to entertain crowds during sunset. You can find everything from musicians and jugglers to artists and tarot card readers, all showcasing their talents against the backdrop of a breathtaking sunset.

What famous houses are in Key West?

One of the biggest attractions of Key West is its historic houses that reflect the architectural style of different eras. 

Harry S. Truman Little White House: The Harry S. Truman Little White House, located at Front Street, was the residence of the US President during his frequent visits to Key West in the 1940s and 1950s.The house is now a museum and hosts a collection of presidential artifacts and photographs.

Ernest Hemingway Home and Museum : This house, located at Whitehead Street, was the residence of Hemingway from 1931 to 1961. Hemingway wrote some of his best-known works in this house, including “For Whom the Bell Tolls” and “The Snows of Kilimanjaro.” The house has a colonial-style architecture and is surrounded by lush green gardens. The highlight of the house is the polydactyl cats, also known as Hemingway cats, which are descendants of the cats that Hemingway kept as pets during his stay.

Audubon House and Tropical Gardens : John James Audubon, the famous naturalist, and painter, visited Key West in the 1830s. During his stay, he painted a collection of 22 birds that are specific to the island. The Audubon House and Tropical Gardens, located at Whitehead Street, was built in the 1840s and is a historical landmark in Key West. The house has colonial architecture and hosts a collection of original Audubon prints, furniture, and artifacts.

The Oldest House Museum and Gardens: Located at Duval Street, is the oldest house in Key West, built in 1829. The house is a perfect example of the Bahamian architectural style that was prevalent in Key West during that time. The museum houses a collection of historical artifacts, including household items, documents, and photographs.

Southernmost House : Located at Duval Street, is a beautiful house that exudes the elegance of the Victorian era. The house was built in 1896 and has a unique combination of architectural styles, featuring both Victorian and Caribbean elements. The house has hosted many important dignitaries, including President William Howard Taft, and is now a luxury hotel.

A visit to these notable houses of Key West is not just a fascinating journey through time but also an opportunity to explore the rich history of this beautiful island.

What's the best way to see Duval Street?

The Conch Tour Train is an authentic way to experience the history and culture of Key West. This 90-minute tour takes you through Old Town Key West, Duval Street, and other popular attractions such as the Ernest Hemingway Home and Museum and the Southernmost Point. Sitting atop the train’s open-air seats, you’ll be able to see the sights and sounds of Duval Street up close while enjoying the breeze. Along the way, you’ll learn about the island’s fascinating history and colorful characters from your expert tour guide.

What attractions are near Duval Street?

Duval Street is undoubtedly one of the most popular and bustling strips in Key West. It brings together great food, unique shopping experiences, and fantastic nightlife. There are plenty of attractions near Duval Street that are worth checking out. 

One of the most popular attractions near Duval Street is the Sunset Celebration at Mallory Square . Every night, locals and tourists alike gather to watch the sunset over the horizon. It’s a beautiful sight to behold, and it’s a great way to end the day. 

If you’re looking for something interactive, the Key West Aquarium and Key West Shipwreck Museum are both great options. The Aquarium is home to a variety of marine life and a great way to learn about marine conservation, and the Shipwreck Museum offers a fascinating look into the history of dangers and adventures of shipwreck salvage in Key West. 

For a unique experience, be sure to check out the Truman Little White House . This historic building was once the home of President Harry S. Truman, and it’s now open to the public for tours. It’s a great way to learn more about the history of Key West and the United States. 

Duval Street is an amazing place to explore, but there are plenty of attractions near Duval Street that are worth checking out. From the Sunset Celebration at Mallory Square to the Truman Little White House, there’s something for everyone. So don’t miss out on all the fun and excitement that Key West has to offer.

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1025 reviews

Old Town Trolley Tours Key West 4.4

Choose Your Tickets

Whether you’re just breezing through or enjoying an extended stay, we’ve got several options to choose from to help you maximize your time in Key West and still see the best first!

1-Day Trolley

• 1 day of free unlimited re-boarding
• Open-air sightseeing perfect for taking pictures
• More than 100 points of interest
• FREE Two Guided Walking Tours included
• FREE admission to the Sails to Rails Museum included
• FREE coupons worth up to $50 in discounts
• 100% satisfaction guarantee
• Exclusive stops and Key West attraction discounts

Ghosts & Gravestones

• Voted Top Ten Best Ghost Tour by USA Today Readers' Choice
• Explore Some of Key West’s Most Haunted Sites…
• Pass by Some of the Most Tragic and Most Sacred Sites of the Island
• Your voyage includes a stop at the Key West Shipwreck Treasure Museum
• East Martello Fort & Robert the Doll are no longer a stop on our tour

1-Day Conch Tour Train

• 1-day tour of the Conch Republic
• One full loop through Old Town Key West
• Includes three stops
• Highlights marvelous sights, stories and entertainment

2-Day Trolley

• 2 consecutive days of free unlimited re-boarding

2-Day Conch Tour Train

• 2-consecutive day tour of the Conch Republic

Key West Aquarium

• Daily shark and turtle feedings
• Touch Tank offers guests hands on experience
• Featuring a wide variety of fish including grouper, moray eels, barracuda, tropical fish, tarpon, parrotfish and more

Truman Little White House

• See the home Harry S. Truman came to relax and rest
• History tellers share fascinating stories of the most important man of his time
• Visit where Eisenhower recuperated from his heart attack in 1956
• Thomas Edison resided here during World War I

Key West Shipwreck Treasure Museum

• Discover the world of Shipwrecking
• Hear the story of the Isaac Allerton
• Climb a 65' Captain's Observatory
• Lift a silver bar salvaged from a Spanish galleon
• Enjoy a video presentation about the shipwrecking industry

Sails to Rails Museum

• Discover the Age of Sail in the Caribbean, Gulf of Mexico and the Florida Keys
• Lift a genuine silver bar
• Enjoy video presentations on the Overseas Railroad
• Hands on, immersive activities

Why use Old Town Trolley Tours in Key West

• Riding around for over 30 years!
• All our tours are 100% live in real time - No pre-recorded narration
• The finest, most highly-trained and knowledgeable guides
• Unlimited hop-on & hop-off as often as you like all day long
• Proudly owned and operated in the United States

Old Town Trolley Tours is

Key west’s best hop-on, hop-off all day tour.

• Best view! Ride high above it all
• Every seat is the best seat!
• Most frequent service
• 13 convenient stops
• Exclusive stops
• Key West attraction discounts

Your Vacation… All Mapped Out For You!

• Trolley Routes & Stops
• Helpful information
• Points of Interest
• Shopping & Entertainment
• Restaurants & Bars
• And much more!

OLD TOWN TROLLEY TOURS

What Our Guests Are Saying

Luis was the highlight of our visit.

We had Luis as our tour guide. First time visit to Key West so I don’t know what the rest of your guides are like, but Luis was the highlight of our visit. When I come back to Key West I will be looking him up to take the tour again. He was informative and very funny. Thanks Luis for the great time.

We had truly the world’s greatest tour guide

We were in Key West last week and had truly the world’s greatest tour guide, Mark. We were so impressed with his kindness, sense of humor and knowledge and pride of Key West that we remained on the trolley for the full 90 minutes!

...The best day of the trip

Mr. History is by far the best guide we have ever had. My wife and I are history nerds and not that we are knowledgeable but we just like getting the history wherever we go on vacation. Mr. History was an absolute well of knowledge. He saved our rainy day and made it the best day of the trip.

Great value for money

Just like to say: brilliant, funny, great value for money; will recommend your tours to anybody going to Key West. Louie, David: very funny guys; had my wife laughing …thanks

This was a first class tour

…We had the opportunity to take an old town trolley tour. My wife and I thoroughly enjoyed it… Our guide Louie, was most informative and so funny at the same time. He made the tour one of the best we’ve ever been on. Of course the history of Key West was very good but the highlight was our guide… I could see the other passengers just waiting on his next comments and his delivery was exceptional from a local’s standpoint!…

What a great tour...

We had the pleasure of having Juni as our tour guide. What a great tour she provided. I’ve always wondered who are the people in the world who love their job. She definitely does. She had such enthusiasm for Key West… Please let her know what a great asset she is to your tour company and to keep up the good work. She was wonderful!

Please keep expanding to more cities

Just wanted to let you know how much we enjoyed our recent tour in Key West. It was all that we expected after we took your San Diego tours a few years ago. I just wish you had a trolley in New Orleans… Special cudos to your excellent guides. Please keep expanding to more cities.

We will be back for a visit

My wife and I were recently in Key West… After driving the island for a few days and finding it hard to park, the concierge suggested your narrated trolley tour. I really didn’t like the idea of a stuffy tour but we went anyway. After the first 5 minutes of laughing almost nonstop, we were hooked. We had a great time and your drivers were anything but stuffy…

Outstanding!

Thoroughly enjoyed your service in Key West. This is our 3rd city to use your services and we have never been disappointed. We really enjoyed Claire as our guide. Very knowledgeable and a lot of fun. Gave us some great tips to help us make the most of our trip. She is a keeper for you!… If we are in any of your other cities we will definitely use your service, it is outstanding!

...A great way to see Key West

We just returned from our vacation and did the Old Town Trolley Tour. It was great! We got off at a couple of stops (had Key Lime pie on a stick with chocolate that was fabulous!) and so got to experience more than one driver/guide. They were all great and the tour is a great way to see Key West in a short period of time…The trolley tour was an absolute bargain!

Old Town Trolley Tours

First tour starts at 9am.

Last tour departs from Mallory Square at 4:30pm.

All schedules are subject to change. Please call for the most current information: (855) 623-8289

For specific information, go to Ghosts & Gravestones schedule .

Reservations are required . Call for availability prior to making your e-ticket purchase:

(305) 294-4678

First tour starts at 9:00 am.

Last tour departs from Front Street at 4:30 pm.

For specific information, go to Conch Tour Train schedule .

What are the most popular stops on the Key West tour route? + -

We take great pride in providing an itinerary that showcases all the great aspects of each city during our tours. The most popular stops on our Key West tour include the Historic Seaport, Duval Street, and the Southernmost Point.

How long is the Key West tour route from start to finish? + -

Our Key West tour is 13 miles long and averages 90 minutes from start to finish, but our hop-on, hop-off tour is designed for you to hop off at any stop, explore a Key West attraction or neighborhood, and hop back on when you are ready to resume your Key West sightseeing experience.

Do I have to start at stop #1? + -

You may start your Old Town Trolley Tour at any of our convenient stops. Click on Map and Stops to see a list of our stops with information about the attractions and points of interest at each stop.

What neighborhoods does the tour visit? + -

The Key West tour travels through Bahama Village, Old Town, Truval Village, and the Historic Seaport.

Does the tour run on holidays and holiday weekends? + -

Our Key West tours run 364 days per year (365 in leap years). We’re closed on the Saturday of Fantasy Fest (October).

How often do tours run throughout the day? + -

Old Town Trolley Tours of Key West operates the city’s largest fleet of sightseeing vehicles, and this allows us to pick up and drop off more frequently than any other trolley company. The frequency of the trolleys depends on the time of the year, traffic, and weather conditions.

How do I get to Mallory Square? + -

One of the must-visit places in Key West is Mallory Square, which is famous for its stunning sunsets and street performers. Old Town Trolley is unique and fun and the most convenient way to get to Mallory Square. The tour takes you through the winding streets of Key West, past colorful houses, lush gardens, and sparkling waterways. The tour guide gives you a brief history of the city’s landmarks, including the Ernest Hemingway Home & Museum, the Southernmost Point, and the Truman Little White House. The trolley takes you to the entrance of Mallory Square, where you can get off and start exploring on foot. You can take a leisurely stroll along the waterfront, admiring the breathtaking views of the sea and the distant horizon. You will also find many street performers here, who entertain visitors with their unique talents, including magic tricks, fire dancing, and acrobatics.

What is the best way to tour Key West? + -

With so much to see and do, it can be challenging to explore the city in a short amount of time. Luckily, there is an easy and convenient way to tour Key West — with a Key West Old Town Trolley Tour. Sit back and relax while the trolley takes you to all the major sites and attractions in the city. With its open-air design, you can enjoy the warm Florida breeze and scenic views while learning about the city’s rich history from knowledgeable tour guides. You can visit popular landmarks such as the Ernest Hemingway Home & Museum, Harry Truman’s Little White House, and the famous Southernmost Point buoy. You can take advantage of packages that include admission to the Truman Little White House, the Key West Aquarium, and the Key West Shipwreck Treasure Museum.

How long does it take to visit Key West? + -

The short answer is that it depends on what you want to see and do. If you’re looking to get a taste of the excitement, two days may be enough. You will have ample time to explore the many museums, art galleries, shops, and restaurants that this beautiful city has to offer. When you’re on a tight schedule and want to experience Key West in a day, Old Town Trolley Tour is the perfect solution for you. The beauty of this tour is that it covers more than 100 points of interest, making it easy for you to hop on and off as you please.

What are the most famous attractions? + -

If you’re planning to visit, don’t miss out on the chance to discover the most famous attractions in Key West. The must-see attractions in Key West include the Ernest Hemingway Home & Museum, the Key West Butterfly & Nature Conservatory, the Historic Seaport District, and the Key West Lighthouse. Additionally, make sure you visit the Southernmost Point buoy, stroll down Duval Street, and enjoy a slice of Key lime pie! The city is rich in history and culture, and an Old Town Trolley Tour is a perfect way to experience and explore the city’s famous landmarks. The attractions mentioned are some of the top-rated tourist destinations that you should include in your itinerary. Don’t miss the chance to visit these fantastic places and see the colorful and lively locations that have captured the hearts of tourists worldwide.

Which street has the most things to do in Key West? + -

If you are visiting Key West, you will want to take a stroll down the lively and vibrant Duval Street. This bustling street is the heart of the city, a veritable hub of tourist activity. It is a must-visit destination that offers something for everyone. From dining and shopping to nightlife and fascinating attractions, Duval Street has it all. The street is home to several historic landmarks, shops, restaurants, and entertainment spots. You can explore the street on foot, by bike, or by taking a ride on the famous Conch Tour Train or Old Town Trolley Tour. The street is home to several popular tourist attractions, such as Crowne Plaza La Concha, Sloppy Joe’s Bar, Kermit’s Key West Key Lime Pie Shoppe, and the Key West Butterfly and Nature Conservatory.

What is the most beautiful part of Key West? + -

The first must-visit location that everyone should see in Key West is the Southernmost Point buoy. This famous landmark is located at the southernmost point of the continental U.S. The buoy has become an iconic spot due to its colorful appearance and its proximity to Cuba, just 90 miles away.

Another stunning vista to experience is Fort Zachary Taylor Historic State Park, located on the southern tip of Key West. Fort Zachary is favored for its beautiful beaches and striking views of the horizon. This lovely spot is a perfect place to enjoy some relaxation, taking in the beauty of the surroundings.

The Old Town Trolley Tour is perfect for travelers who want to explore and witness the beauty and history of the city.

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Key West HISTORIC MARKER TOUR

Captain george carey house, the key west woman's club, casa antigua, james haskins house, la concha hotel, the oldest drug store, the southernmost house, the oldest house, william wall warehouse, dr. joseph yates porter house.

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• Key West Morning Mimosa Private Charter

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Key West Food Tours

Our mission, key west food tours was founded in 2014 to offer visitors of key west a taste of authentic local culinary experiences while providing historical anecdotes, because, let’s face it, food tastes better when there’s a story behind it, here in key west, food is an art, and art is what we know best. we islanders are known to be laid-back, creative, wacky, & friendly. well, the chefs are no different. , we provide unique and original local culinary walking tours in a safe, sustainable, and environmentally responsible manner. our goal is to create food memories that last a lifetime. by taking visitors off-the-beaten-path, you’ll discover engaging and knowledgeable local guides who are eager to share the most authentic and delicious version of key west. , here at key west food tours, our team and tour guides are dedicated to giving you the best experience possible, while filling your bellies up with local favorites. we want to show you what our island has to offer: a rich history with cultural influences, and tasty local food, analise andrews, owner & founder.

Raised in her Cuban grandmother’s Key West kitchen, and armed with a business degree, Analise Smith pursued a career in the food industry by starting Key West Food Tours in 2014. Combining a love for food with her hometown of Key West, Analise created a 3-hour, highly entertaining narrative weaving the island’s history on a tasting walking tour, visiting five local mom-and-pop restaurants.

Today, Key West Food Tours consistently receives #1 in TripAdvisor’s Food and Drink category for Key West, as well as TripAdvisor’s Certificate of Excellence.

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Shannon McRae, General Manager

A native Floridian, Shannon was the first to join the KWFT Team. Starting as a guide, she knows the tours and the Key West food scene inside and out.  Now she’s helping run the show from behind the scenes, but still takes any opportunity to fill in and lead a tour.

Local fave: Stone Crab claws and key lime mustard!

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Shayla Patten, Operations Manager

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Rose Chambliss, Guide

Rose may be a New Yorker by birth, but he’s a Florida man at heart. This smooth-talking gentle giant has a soft spot for our Historic Seaport Tour and Cocktail Crawl. Even though he works clear over 40 hours a week at multiple jobs, he will always have time to take you and yours out for a stroll around our beautiful turquoise waters!

Local Fave: Lobster ravioli from Nine One Five

Maxwell Irwin, Guide

Maxwell is one of those few mythical creatures walking among us, (no, not a unicorn) a Key West Conch! Born and raised on local seafood and music, Maxwell spends his spare time playing in bands around the island when he’s not showing our guests around the historical neighborhoods he called his childhood playground.

Local Fave: Conch salad

Dana Calyton, Guide

From one historic port to another, Dana came to us from Charleston, SC. She may be newer to guiding, but that’s only because she’s a physician’s assistant at our local emergency care clinic. Hopefully you’ll only be seeing her on tour, but rest assured you’re in good hands either way!

Local fave: Thirsty Mermaid’s Yellow tail Snapper

Chris Gaskill, Guide

Born in Marathon with a passion for the hospitality industry, Chris grew up helping his mom with work in Key West before going out on the town for dinner after. Love for local cuisine influenced him to attended the Culinary Institute of America in NY, before returning to the FL Keys to be the Sous Chef for Chef Signature Flavoring Catering when he’s not touring with us!

Local fave: Macadamia nut Crusted Mahi with a Coconut Rum Sauce and Papaya Mango Salsa

Breana Sowers, Guide

Originally from Indiana, Breana has been an island girl for 8 years. She works full time as the Archivist for Monroe County in the Florida Keys History Center. Breana loves local history, traveling anywhere, taking in the sunshine, and running by the water at sunset.

Local fave: grouper cheek tacos from Off the Hook or Jerk Wings from Kaya

MajorieElla Krebs, Guide

Hailing from NY/NJ, MajorieElla has made the FL Keys her home going on 11 years and counting. Her passions include the culinary arts, home chefing, and stealing recipes from everyone and everywhere.

Local Fave: Florida Lobster in Truffle Butter from Louie’s Backyard

Sharon Dickinson, Guide

Keila mendez, guide.

Keila’s love of food may have been what originally brought her here to Key West, but it’s only one of the reasons she decided to stay and make it home! After moving here to help open a Seafood Truck, she discovered Key West’s rich history as well and fell in love with the island. When she’s not working, cooking or checking out the best new restaurants in town, she’s out on the water – she loves paddle boarding, kayaking and cruising out to the sandbars. While on tour she loves to share her love of the island with everyone.

Local fave: Whole fried snapper from El SIboney

Sara Good-Chanmugam, Guide

Sara was born and raised here in Key West to a large restaurant family. She is super passionate about food systems, from growing, to distribution and consumption, and especially with decomposition (composting). When she’s not kayaking, or digging in the local garden, she’s always excited to share some Key West history with her guests!

Local Fave: Goat curry from Pepper Pot Island Cafe

This is how our food tours look like!