long island brewery bike tour

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Riverhead Long Island

Riverhead long island overview.

When in Riverhead, take a tour with Brew Crew Cycles! It is the best way to pedal around the Eastern End of Long Island experiencing local breweries in Riverhead, while enjoying a beverage on your way! These 14-person bikes make brewpub tours a great group experience. During the 2.5-hour ride Brew Crew Cycles takes riders, as fast as they can pedal, to their next ice cold brew. This bike tour is a unique way to experience two local breweries and drink onboard the bike.

What To Bring

• Bring Your Own Snacks/Drinks to enjoy while onboard the bike! 3 drinks max/person
• Fun Clothing or Costumes
• Closed toed shoes for on the bike tour
• Sunscreen/Rain Gear
• A good Attitude
• 14 Friends!

Drop off Point

The tour starts at 205b Marcy Ave, Riverhead, NY 11901, United States, you can find us on google maps by searching for Urban Pedal Tours Long Island

*Arrive 15 minutes before your tour’s planned start time!

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Rules on the Bike

• No glass on the bike
• Don’t Lean Into Traffic
• Hold on at All Times
• Pedal on Command (You Bring the Power!)
• Don’t use Foul Language
• Have Fun & Leave a Good Review!
• Wear Closed Toe Shoes

Absolute Best Long Island Brewery Tours

There is an explosion of Long Island breweries over the past decade. There is no better way to experience all of this than with some great Long Island brewery tours !

Brew Crew Cycles

One of the most fun and innovative of the Long Island brewery tours has to be from Brew Crew Cycles. This company is uniquely positioned as Long Island’s party bike and beer experience!

The 14-person bikes help you to work off those suds-induced calories by making you pump your way from brewpub to brewpub! Brew Crew Cycles riders will visit 3 local Long Island breweries during the 2-hour tour. This is plenty of time to try the excellent craft beers being produced on Long Island.

While it’s great to get a workout while sampling, it’s also great because you’re not driving when you’re drinking!!

Book a tour date in April or May and receive 15% off with code EARLYBIRD2020. Check out https://www.brewcrewcycles.com for more.

Long Island Beer Bus

If you’re in the mood for a workout while you drink, then maybe the Long Island Beer Bus by Tapped Enterprises is the for you.

Tapped Enterprises specializes in private brewery tours, wine tours, corporate outings, trips to sporting events, beer festivals, and custom event planning for people of all ages. 

Since Long Island breweries are spread out Island-wide, it’s great that Long Island brewery tours like the one cover all the areas! There’s a North Fork tour, a Riverhead tour, a Beer and Food Truck tour! You can even create your own private tour! The list of options is long and comprehensive.

Find out more at libeerbus.com.

L.I. Brew Bus

Another great option when you are looking for Long Island brewery tours is the L.I. Brew Bus.

The bus looks great and the tours are even greater! With over 40 Long Island breweries from Montauk Point to Manhattan, every L.I. Brew Bus Tour is unique and ever changing. Last year over 6 Breweries opened on Long Island with a lot more coming!

To find out more, check out LIbrewbus.com.

Long Island Brewery Tours

After seeing great success with their Long Island winery tours, the owners figured they could for for beer tours Long Island what they did for win tours. They started Long Island Brewery Tours to service the ever-growing list of new breweries starting up on the Island.

On this beer tour Long Island, you will visit up to 3 Breweries and sample an average of 15-20 different Pilsners, Ales, Drafts & Stout’s. Our Beer Tours are like no other. Most Brewery Tours start at 11 am in the morning, but can be changed to accommodate your schedule if need be.

Find out more by visiting LongIslandbrewerytours.com.

More About the Beer

If you can’t make it out for a tour, be sure to look into beer delivery !

Check Out What’s New In Long Island Brewing for 2020 and 2021!!!

Read more about some of the best Long Island craft beer around!

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The bounty of great food on Long Island seems endless! From great  steakhouses on Long Island  to great  Greenport restaurants , there’s so much to enjoy. And how about all the wonderful  restaurants on the water Long Island ?! Or maybe check out some  Long Island oyster farms !

Be sure to find out about more  things to do on Long Island  as well as more great spots to  eat and drink  and wonderful  places to stay  on Long Island!

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BREWERY & VINEYARD TOUR

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• 631–871–1666

On this guided bike tour cycling through north fork’s wine country, seasoned guides will lead you to 1 vineyard, 1 brewery, and in between cycle to a tranquil beach for a hydration break & revitalize your food palette as you taste fine vinegar and herb infused olive oils from Long Island’s Crushed Olive! Take an enchanted ride experiencing the breathtaking views of the charming north fork. Check out one of the very first farm stands that begin on the north fork over 50 years ago for amazing fruits, pies, veggies, honey, & jam. You’ll join a small group led by a local, knowledgeable tour guide who will curate and enhance your understanding of the north fork and the romantic vine-to-bottle process. Tours are led at a casual pace. The emphasis is on enjoying the scenery and highlighting the best of the north fork with you from the seat of a bicycle which is spectacular. Put the sparkle back in your state of mind and indulge in this lovely and unique wine country bike tour because wine’ not!

Experience a unique blend of activities throughout the day. Expected on this tour are:

Cruise North Fork Long Island on a single or tandem bicycle (or even on an E-Bike!)

Enjoy unlimited non-alcoholic refreshments throughout your tour experience to stay energized while riding from location to location

Our professional guides will direct you through the beautiful landscape, leading you from winery to brewery and more

Gain privileged access to wander vineyard fields

Delight in extra-virgin olive oil & fine vinegar tastings to infuse your pallet with local flavors

Pay a visit to local farm stands where you can purchase up freshly made jams, pies, fruits, and vegetables for your home

Stroll down Love Lane after the tour for a one-of-a-kind shopping experience. (only 1 block from our location)

We also include a support vehicle to transport any purchases made along the way

Seasoned guides will capture moments from your day, photos will be available for free download

*Includes one flight of wine tastings*

It is strongly recommend to book 4 weeks or more in advance for your preferred date.

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A Guided Bike Tour of Breweries and Vineyards

GUIDED BREWERY AND VINEYARD BIKE TOURS THROUGH THE NORTH FORK’S WINE COUNTRY

Pedal your way to the taste of the North Fork wine country; explore breweries, wineries, and more. Enjoy a guided  “ Vineyard Bike Tours” brewery and vineyard tour through the North Fork’s Wine Country. The North Fork has well-organized guided bicycle tours of the area’s wineries, breweries, and farm stands.  You’ll enjoy riding through the tree-lined streets of the various hamlets and enjoying the scenic views of the Peconic Bay.  You’ll see historic landmarks and beautiful vineyards.

The organizers pay attention to the details of your dietary request and make sure your trip is well documented.  Riding through the North Fork is like no other experience you’ve had.  Normally you’d be zipping past important landmarks without knowing their history and significance.  They are passionate about cycling and bring that to their creation of this event.

Vineyard Bike Tours

• Cruise the North Fork Long Island from the seat of a single or tandem Hybrid bicycle (Helmets Included)
• Enjoy unlimited non-alcoholic refreshments throughout your tour experience to stay energized while riding from location to location.
• Professional guides will direct you through the beautiful North Fork landscape, leading you from winery to brewery and more.
• Gain privileged access to wander vineyard fields.
• Enjoy extra-virgin olive oil & fine vinegar tastings to infuse your pallet with local flavors.
• Visit local farm stands and purchase freshly made jams, pies, fruits, and vegetables for your home.
• Stroll down Love Lane after the tour for a one-of-a-kind shopping experience
• Take advantage of a support vehicle to transport any purchases
• Expert guides will capture moments from your day; photos will be available for free download
• Duration: Approximately 5 Hours
• When: Sundays, August 7,14,21,28 at 10 am -3:30 pm
• Where: East End Bike Tours
• Distance: Approximately 14-18 miles (dependent on the selected route)
• Cost: $ 96-$155

“ This bike tour was by far the best part of my North Fork Weekend. I can’t say enough good things about it. ”

CHOOSE YOUR ROOM HERE

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Urban Pedal Tours Long Island

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Urban Pedal Tours Long Island - All You Need to Know BEFORE You Go (2024)

• Food and Drink
• Beer Tasting

Brewery and Winery Bike Tour in Long Island

Cycle Your Way Through the Best Wineries and Breweries North Fork Has to Offer During This Five Hour Tour

• • Long Island Winery and Brewery Cycling Tour
• • 5 Hour Cycling Tour through Stunning North Fork
• • Tandems Available for Romantic Couple's Activity

Why We Love This Unique Experience

Long Island Experience Gifts: Explore the wineries and breweries of North Fork with this incredible cycling tour through the stunning landscapes of Long Island. 

If you’re fascinated to learn more about how wine and beer is made and happen to be vacationing in New York or Long Island, then a trip to North Fork to take part in this cycling tour of some of the best local wineries and breweries could be the ideal vacation activity for you. This 18-mile route is not for the faint hearted so would suit a keen cyclist or fan of outdoor activities, but the stunning scenery is well worth the effort as you pedal to and explore beautiful vineyard fields. You’ll get to taste different flavors of the delicious local virgin olive oils and other locally made produce likes jams and pies. You’ll even be treated to complimentary soft drinks to keep you refreshed and energized during your journey. Tandem bikes are available, making this the perfect romantic activity to celebrate that special anniversary. 

This very special winery and brewery tour through stunning countryside would be the perfect anniversary gift to treat that happy couple vacationing in Long Island or even living close by in New York. 

Check Availability & Book

Experience overview:.

Beer and wine! Now that’s something for everyone. Explore both the wondrous wine culture of North Fork Long Island and pedal your way to local award-winning breweries. 

Distance: Approximately 13.5 miles

A La Carte Features

• Cruise North Fork Long Island on a single-use or tandem bicycles
• Enjoy unlimited non-alcoholic refreshments throughout your tour experience to stay energized while riding from location to location
• Our professional guides will direct you through the beautiful landscape, leading you from winery to brewery and more
• Gain privileged access to wander vineyard fields
• Delight in extra-virgin olive oil & fine vinegar tastings to infuse your pallet with local flavors
• Pay a visit to local farm stands where you can purchase up freshly made jams, pies, fruits, and vegetables for your home
• Stroll down Love Lane after the tour for a one of a kind shopping experience (only 1 block from our location)
• We also include a support vehicle to transport any purchases made along the way
• Seasoned guides will capture moments from your day, photos will be available for free download

> More Experience Gifts in New York City

Cancellations & refunds, reservation changes, cancellations & refunds.

Changes to reservations for tickets can be made until 31 days prior to the date scheduled. Reservations may be re-scheduled by the operator of the activity due to reasons such as weather, minimum participation requirements, mechanical issues or other interruptions beyond their control.

All gift certificate sales are final and not refundable. Gift certificates can only be exchanged prior to redemption.

A full list of terms of sale of tickets and certificates can be viewed here .

Organized by

East end bike tours.

Our trips are designed for those who are seeking to sight-see, indulge, sample, photograph, shop, and exercise all in one adventure. Along our breathtaking route, you will enjoy the picturesque views that Long Island’s Wine Country has to offer.

Your unforgettable experience begins when you arrive in Mattituck at our meeting point. After meeting your guide and sharing an overview of the details of your trip, you get introduced to our fleet of tandem and hybrid bikes and fitted with the frame perfect for you. You then pedal the rolling terrain that runs along the Peconic Bay, between the North and South Fork of the Island. The day is filled with breathtaking itineraries and hand-picked stops along the way to combine the best in classic cycling with the best cultural experience we’ve seen.

We intersperse plenty of pauses to refuel your body and spirit with delicious snacks and aperitifs, stops for photos of panoramic vistas and strolls in the charming towns we ride through. Pedaling a gentle 13.5-mile route, you will enjoy approximately 1.5 hours of pure cycling pleasure while also having the time to slow down and enjoy the Bella Vita (beautiful life) that Long Island is famous for.

Product SKU: US-0756-0012 Google Business Profile: East End Bike Tours

How It Works

Best experience providers.

Our Activity Partners are highly rated and experts in what they do, guaranteeing you an unforgettable experience.

Free Gift Exchanges

All ExperienceGifts Certificates are fully exchangeable if you change your mind, free of charge!

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Our beautifully designed e-certificates are sent instantly the moment you place an order, great for last minute gifts.

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Guide: Brewery and Vineyard Bike Tours

<p>want a unique way to check out some of long island&rsquo;s breweries here is a list of bike and bus tours offered on the east end, as well as other parts of long island.&nbsp;</p>.

News 12 Staff

Jul 26, 2018, 9:00 AM

Updated 2,144 days ago

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Guide: Brewery and Vineyard Tours on Long Island

Want a unique way to check out some of long island’s breweries.

News 12 Staff

Mar 31, 2023, 3:46 PM

Updated 435 days ago

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It's Time for Tacos & Beer!

Bike to the Brewery

Let's Ride for the Long Island Greenway!

In partnership with

Just show your rider I.D. wristband to get your free beer and tacos. (We're good for a couple of beers and the first round of tacos -- all included in the price of the ride. If you're still standing after that, you are on your own Jack!)

How to Get Home

Home? Why leave?

OK, if you insist.

1. Have your friends meet you at the brewery and give you a lift home. It's a great place and a lot of fun.  Plenty of free parking. Your tacos and beer are included in the price of the ride; your friends can purchase food and drink at reasonable prices.

2. We will offer optional transport back to Bellmore and NYC. You pay us to transport your bike ($25) and you take the LIRR train. (Buy your own ticket, or use your monthly pass).

About Parks & Trails New York

Parks & Trails New York (PTNY) is New York’s leading statewide advocate for parks and trails. Since its founding in 1985, PTNY has been fighting to improve our health, economy, and quality of life through the use and enjoyment of green space. In collaboration with members, supporters and partners from across the state, PTNY is a prominent voice for the protection and expansion of New York’s magnificent state park system and multi-use trail network, including more than 1,500 miles of greenways, bike paths, and river walks. Learn more at www.ptny.org .

Questions? Comments? Always glad to hear from you.

Another Swell Ride from Yer Old Pal Glen

Saturday August 26, 2023

40 Miles • 60 Miles

No Fundraising

• Limited to 200 riders only! •

Blue Point Brewery? We go way back with these folks!

(No, we do not have extra copies of ANY of those jerseys!  If you have one, hang on to it!)

We are long overdue for a tacos and beer run, and I am ready. Let's pedal to the Blue Point Brewery and kick back.

All credit due to our friends at Trust for Public Land as well as Parks & Trails New York , organizer of the well-loved Cycle the Erie Canal bike tour from Buffalo to Albany, and the new Cycle the Hudson Valley bike ride from Troy to NYC. Parks & Trails New York is partnering with me to bring you this great ride, which will also support completion of the Long Island Greenway. Come help us advocate for better cycling on Long Island... and have some great snacks, drinks, and sights along the way.

What? Where? How?

Relax!  We've made it easy.

(We'll remind you of all these details later, but here's a sneak preview).

60 Mile Route

Start your day by taking the E or J subway with your bike to our start line at the Sutphin Blvd - Archer Av - JFK Airport subway station.  

A) Just pretend I know what I'm talking about.

B) Unlike the LIRR, the subway allows bikes in quantity.

C) We wanted to skip some of the more difficult sections of pedaling and get to the fun.

D) It's a respectful nod to the old days (before my time) when folks who were pedaling from NYC to Montauk would gather out this way and... stand around, drinking coffee and wasting time until someone said, "OK, let's go." In those days no official rest stops, no marked route, no GPS files... just ride.

I read the Cambelback owner's manual carefully, and I'm pretty sure this is not an authorized use....

40-Mile Route

The 40-mile route starts pedaling from the Bellmore, Long Island LIRR station. You are on the same route as everyone else -- you just start pedaling a bit closer to the finish line.

You can get to Bellmore on your own, OR you can meet us at the NYC start line and we will transport your bike to Bellmore for free. You get to Bellmore by paying for your own train ticket from NYC (or use your monthly LIRR pass).  A friendly reminder that you can NOT take your bike on the train -- that's why we transport it for you!

Hempstead Lake State Park no-car bike path -- the 60-mile routes go here.  Fully paved.

Of course if you'd rather pedal to the Sutphin Blvd subway station stop instead of taking the subway it's OK with us!

Pedal from Sutphin Blvd to the Blue Point Brewery.  Go at your own pace or ride with our official escort leaders. Of course there will be swell snack stops and full support. About 20-miles in we'll be joined by our friends who are starting the 40-mile ride from Bellmore, Long Island. Same route -- they just start closer to the finish line.

Heckscher State Park no-car bike path. The 40- and 60-mile routes will both be pedaling this lovely section.

Whether you're doing the 40-mile route or the 60-, right before the brewery finish line all cyclists will stop to see some good friends of Parks & Trails New York at the beautiful Snapper Inn restaurant, where they will be providing an amazing snack! (Yes, really...)

When we reach the finish line at the Blue Point Brewery we'll celebrate with free beer and tacos. (Yes, it's Taco Tuesday... on a Saturday!)  

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Long Island Brewery Tours

• Brewery Tours

Long Island has long been known for having its own little wine country out east, popular with locals and visitors alike, but in recent years another beverage has been making a home for itself on the Island. Dozens of craft breweries have popped up all long Nassau and Suffolk County, purveying all manner of stouts, lagers, ales, porters, and other delicious beers to an adoring local market. With so many great microbreweries to choose from it can be a bit difficult to decide where to go, but you don't need to pick just one. Alongside all the great new breweries, ... Read More Long Island has long been known for having its own little wine country out east, popular with locals and visitors alike, but in recent years another beverage has been making a home for itself on the Island. Dozens of craft breweries have popped up all long Nassau and Suffolk County, purveying all manner of stouts, lagers, ales, porters, and other delicious beers to an adoring local market. With so many great microbreweries to choose from it can be a bit difficult to decide where to go, but you don't need to pick just one. Alongside all the great new breweries, tour companies have also started up to help you make the most of all that LI's beer scene has to offer. You won't need to pick just one brewery when you and your friends can be safely escorted from one brewery to the next by a professional driver. Show Less

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Beer Bus by Tapped Enterprises

PO Box 1597 in Ronkonkoma 631-913-3817

Want to be added to the Brewery Tours Page? Call 631-406-4410 or Email Us for details!

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Long Island Bicycle Tours

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Places to Ride on Long Island

Bethpage Bikeway

This scenic trail brings you through State Parks, wetland preserves and town parks. Pick your own pace and mileage as you pedal on the Bethpage Bikeway. 

Jones Beach Bikeways

The Beach bikeway's are paved, traffic-free and meander through a variety of scenic coastal environments, with views of the Great South Bay and Atlantic Ocean.

Belmont / Babylon Loop

An easy 12 mile loop of trails & quiet roads to show the best of Belmont Lake State Park & Babylon Village & Water Front.

You are responsible for your own safety, and a suggested route in no way guarantees that the route is absent of all hazards, including but not limited to: potholes, sketchy pavement, loose gravel, nails, glass, dirt, dust, and other cyclists. Not responsible for errors.

Copyright © All Rights Reserved. Long Island Bicycle Tours Long Island, New York Email: [email protected]

Montauk & Eastern Long Island Bicycle Tours

The Hamptons • Shelter Island • The North Fork

Montauk Point, with it’s lighthouse and rocky shoreline, is one of New York State’s most iconic landmarks

Private tours for small groups. pricing depends on your chosen itinerary as described on our private tours   webpage..

Riding to Montauk by bicycle, or anywhere on the eastern end of Long Island, is a fantastic experience. You can ride on low-traffic roads past stunning landscapes with beautiful beaches, sand dunes, wildlife areas and mansions. Wineries and farms on the North Fork also offer a beautiful setting to sample some of this region’s food and wine.

You can experience the joy of riding in this beautiful region with a customized tour package of any length and duration. No matter what you are looking for, we can put a package together for you after an initial consultation. Our overnight tours can feature a range of accommodations from camping to luxury hotels and you can choose how much you would like to ride each day. Or choose a day ride and get the same level of personal service, with all of your bags and equipment carried in our support vehicle while you ride.

Contact us to get started on planning your Long Island bicycle adventure! We will respond within 24 hours to ask you about your preferences and then put a tour together for you. Based on that discussion, we would tailor a ride for your group that would include GPS navigation for all riders, carrying of all your gear, as well as break stops set up just for your group with snacks and beverages.  And if your bike breaks down or you need help, we are always close by with our support van. 

Check out a suggested itinerary below. For information about how our private tours work and pricing, please see our  private tours page.  We also offer Hamptons Bicycle Getaway packages. 

Example 2-Day Trip Itinerary

Choose routes ranging between 20 and 60 miles. generally flat, with some hills in certain areas..

Depending on the length you want to to ride, we will meet you at a designated start point. If you want to take the train to the ride, a good launch point is the Southampton LIRR station.  If you are driving, we will find a place where you can park for the duration of your trip. No matter how you arrive, you’ll have access to our support van to store everything you do not want to ride with, such as bags, equipment, etc. We will also provide you with snacks, energy bars and beverages to get you on your way.

As you ride through the Hamptons, you will find yourself in a world of where beautiful landscapes, historic villages and extreme wealth meet. Fortunately for us, these towns have many bike friendly roads that allow you to take it all in.  While some visitors never leave the “main drag” of Montauk Highway, we will take you on back roads to see this fascinating area up close. 

A shorter ride might end in Sag Harbor or Amagansett. A longer ride might include a trip out to Montauk Point.  No matter which ride you choose, you’ll have opportunities to stop at beaches, historic sites, farm stands and wineries. Our camping tours feature beach side camping and a cookout dinner. Or stay with one of our partner hotels and enjoy a great dinner in town.

Choose routes ranging between 20 and 60 miles. Generally flat, with some hills on Shelter Island.

If you biked through the Hamptons on the first day, try Shelter Island and the North Fork for your second day. Ride a little or a lot – either way you will experience beautiful landscapes, secluded beaches and many, many wineries. Low traffic roads connect everything together, and we can meet you with our support van at a beach for a swim, or at a winery for a rest stop.

For departures back to NYC by train, we recommend ending the ride in time for the 6 p.m. train back from Greenport.  This train will get you back to the city by 9 p.m.  For people driving to a tour, we can have you end at your cars, or we can shuttle you back if the distance is too far.

The route and planning for both Montauk and Hudson Valley were exceptional. While I have spent much time in both regions, seeing it from a bike was ideal. Such beautiful scenery from all the back roads that you have discovered and shared with us.”

Wanted to say a huge “Thank you” to Laura and Lukas for taking care of me and my friend Liz this past weekend on the Montauk tour! Neither one of us had any experience riding long distance (15 miles the most we have done); we also had no experience with planning the route or planning to emergencies, nor did we have time to do it. I also do not have access to a car nor have I ever changed a flat tire! Everything was very well organized and seamless! The routes where easy to follow and very safe and scenic. My friend and I ended up riding together (not with the rest of the group) as my pace was slower than other’s and following the route was not an issue at all given how clear all directions were. Everything was as described on the website and all our expectations were met above and beyond! Laura and Lukas have a passion for introducing people like us to riding in a low stress safe environment and are lovely people to be around. They also introduced us to other resources on outdoor activities. Perfect activity for busy New Yorker who likes to be active and to explore and who wants to be outside away from it all, spent time with a friends or do a solo activity with or without other riders. I will definitely be doing more riding with Gotham Bikes in very near future!

Upcoming Bike Tours

• Empire State Trail Vacation Tour
• Hudson Valley Craft Brewery Bike Tour
• Empire State Trail Day Tour
• Hudson Valley Food, Wine & Spirits Day Ride

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• THINGS TO DO

Welcome to Long Island Tours

Find the perfect tour of long island.

Long Island is an area of New York that offers diverse culture, plenty of opportunities for entertainment, great food, sporting events, exciting nightlife and an incredible history. Taking a tour of Long Island from one of the many touring companies in Long Island can give you a unique look into what makes Long Island special.

You can start the day by exploring the vineyards here in Long Island. There are some amazing vineyards tours and / or winery tours available throughout Long Island that will have you sampling some of the finest wines in Long Island. If you prefer to get some exercise and fresh air while you taste great wine, you can take a bicycle winery tour .

If you prefer beer over wine, consider taking part in a brewery tour on Long Island. You will get to see how the beer is brewed and taste some of the finest beer brewed on Long Island.

After a brewery tour, maybe you want to take in a stadium tour and see some of the most famous stadiums on Long Island. Yankee stadium, Madison Square Gardens, Citi Field Stadium and others are all available for touring.

There is no better view of New York then from a helicopter. If you want to create a memory that will last a lifetime take a Long Island sky tour and see Long Island, NY from the air. See New York in a way that most people don’t get the chance to see it with a helicopter tour of Long Island.

If getting out on the water is more to your liking, there are great whale watching tours available. Seeing whales up close is an amazing treat. It also offers incredible views of the New York skyline and terrific photo and video opportunities.

You can also take in a bit of history with a lighthouse tour . You can take Long Island light house tour by boat or by bus or van. It is fun to see these historical light houses and learn the stories behind them that make these historical artifacts unique.

Speaking of history… there are great long Island walking tours available by different tour companies. You can get a walking tour that will take you to many of the historical places in Long Island and learn about the history of Long Island as well as take in some great food, sightseeing and shopping.

If you prefer an old fashioned type of travel then check out one of the Long Island trolley tour companies. They can show you a unique side of Long Island that will show you different sides of Long Island and its great restaurants, stores, stadiums, and more.

Whatever it is that you want to do or see on Long Island, choosing a tour from one of the many touring companies throughout Long Island can be the perfect way to see all that Long Island has to offer. Discover the diverse history of Long Island, explore the many restaurants run by rock-star chefs, take in a sporting event or shop to your heart’s content. Long Island offers something for everyone and a Long Island Tour is the perfect way to uncover many of the sights, smells, sounds and tastes that you might not discover on your own.

10 Things To Do On Shelter Island That Show Off A Unique Side Of Long Island

• Shelter Island in New York is a peaceful getaway with nature, small family restaurants, bars, and beautiful beaches. It's a paradise for New Yorkers.
• The Havens' House Museum offers a glimpse into Shelter Island's past, with exhibits, a farmers' market, and antique car shows. Admission is free.
• Visitors to Shelter Island can enjoy activities like biking, exploring Sylvester Manor, hiking in Mashomack Nature Preserve, and relaxing on the pristine beaches.

Between the North and South Forks of Long Island, New York, Shelter Island is a charming 29-square-mile island with quaint homes and impressive houses hidden behind tall, well-manicured hedges. Known for its peaceful beaches and bikeable roads, Shelter Island has unveiled new breweries, restaurants, and hotels, attracting many visitors from Long Island, New York, and ever farther away.

The Island is a calling for people who want to ' get away from it all ,' walk in the woods, bike on beautiful tree-canopied winding roads, collect shells, and de-stress. There's a lovely nature preserve, several good restaurants, and some hotels and inns.

There is a soul to Shelter Island, one that makes it exclusive! Without the noise or any marketing spiel, the island is a New Yorkers' paradise, a small island with small family restaurants, bars, and beaches. Discover some of the best things to do on Shelter Island , Long Island, that show off a unique side to what is one of the best vacation destinations in New York.

Related: 10 Of The Most Unique Places To Visit On Long Island

Visit The Havens' House Museum

Havens' House Museum is a fascinating glimpse into Shelter Island's past and how life was on the island. The Shelter Island Historical Society manages the museum and protects thousands of irreplaceable maps, documents, and artifacts collected over the years.

Havens' House Museum also features the local farmers' market just outside the building, antique car shows, and the Havens Store, which features books by local authors, unique locally-made merchandise, nautical maps, and much more.

Haven's House was built in 1743 and went through a few owners before being finally sold to the Historical Society in 1966 to prevent it from neglect and deterioration. In 1986, the Havens House was placed on the New York State Register of Historic Places and the National Register of Historic Places.

• Museum Location: 16 South Ferry Road, Shelter Island, NY 11964
• Hours Of Operation: Monday through Saturday: 10:00 a.m. to 2:00 p.m. (Sunday Closed)
• Admission: Free
• Duration: Suggested 1 hour to browse the museum

Experience The "Magical History Tour"

This experience is an hour-long guided tour of sites and scenes steeped in Shelter Island history. The Magical History Tour is sponsored by the Shelter Island Historical Society and is conducted every Monday morning.

The mini-bus for the tour departs the newly renovated history center at 10:00 a.m. every Monday, and all guests are invited to the Museum post for the tour and to visit the exhibits.

• Ticket Prices: $40 per person. Visitors can reserve tour tickets online .
• Timings & Schedule: The 10:00 a.m. tour bus leaves every Monday from the history center.

Related: 14 Things To Do In Long Island: Complete Guide To New York's Beach Getaway

Bike On Shelter Island

The only way to get to Shelter Island is by boat. Although cars are allowed on Shelter Island , getting around without one might just be the best decision. Biking off the ferry instead of driving a car will transform a visit to this beautiful island into an honest exploration.

During the Peak season (May - October), no parking spaces will be available, especially near the beaches, and the off-season is the opposite with nobody around. Biking is the best thing to do in both seasons, one for convenience and the other to enjoy the island's winding roads, beautiful scenery, and slow pace of life. If renting a bike, travelers should always remember the do's and don'ts while renting a bike .

• Bike Rental: There's only one bike shop on the island - Piccozzi's Bike Shop
• Get Your Own: Travelers should bring their bikes or rent one before reaching Shelter Island.

There is a private electric bike tour available, but the TripAdvisor page lacks reviews.

Explore Sylvester Manor

Established in 1652 as a provisioning plantation for the Barbadian sugar trade, the Sylvester Manor is one of the top attractions on Shelter Island, Long Island, and it has been under the same family ever since. The former plantation area covers farm fields, wet and woodlands, formal gardens and grass lawns, numerous barns and buildings, and the Manor House.

Though the private home is not open to the public daily, visitors are welcome to wander the beautiful grounds 7 days a week and pick up organic meats and produce at their Farmstand.

About Sylvester Farmstand

• Location: 21 Manwaring Road, Shelter Island, NY 11964
• Timings: Friday through Sunday | 9:00 a.m. - 5:00 p.m.

Go Hiking In Mashomack Nature Preserve

Hiking is easily one of the best activities on Shelter Island, especially when strolling through Mashomack Nature Preserve. Taking up nearly a third of Shelter Island, this 2,029-acre nature preserve, edged by 12 miles of coastline, covers tidal creeks, mature oak woodlands, fields, and freshwater and saltwater marshes. Nearly 200 bird species have taken refuge here.

The US has some incredibly beautiful hikes all across the country and Shelter Island does its bit to contribute. There are five well-marked hiking trails of various lengths in this green gem of New York. With 12 miles of shoreline, 45 small ponds, and 7 salt marshes, there's plenty to do and see here.

• Visitor Center: An interactive visitor center with "please touch" exhibits
• Location: 79 South Ferry Road, Shelter Island, NY 11964
• Schedule: Wednesday through Monday | 9:00 a.m. - 5:00 p.m. (till 4:00 p.m. in winter)

Trails Inside Mashomack Preserve

• Red Trail: 1.5 Miles mostly wooded trail.
• Yellow Trail: 3 Miles of open meadows to see lots of Bluebirds.
• Green Trail: 6 Miles of meadows, woods, and 3 salt marshes
• Blue Trail: 10 miles with stunning views of the Gardiner's Bay

The preserve is free to enter, but there is a sign of a suggested donation of $3 per person.

Enjoy The Pristine Beaches Of Shelter Island

Shelter Island has five beach fronts for visitors and residents to explore, relax, and soak in nature's bliss. Each beach has its uniqueness and is worthy of exploring.

Time on the Beach makes up for a large portion of activities to do in this hidden gem of Long Island.

• Tranquil Shell Beach: Faces the West Neck Harbor and the bay on the other side.
• Crescent Beach: A popular bay beach; it has a lifeguard and public restrooms, plus its calm waters make it perfect for paddle-boarding
• Wade Beach : There are always lots of kids and a lifeguard.
• Silver Beach: Facing the Peconic
• Hay Beach: For its stunning views of Gardiner's Bay

All beaches require a town permit to park.

Take Part In The Annual Activities On Shelter Island

Shelter Island is known for annual events that are great for everyone to enjoy and participate in. These are mainly to promote the island's community and business and preserve any traditions.

Some of the best events on Shelter Island include the Shelter Island 10K and 5K run/walk, Shelter Island Fireworks, and Shelter Island Chamber of Commerce Art Show and Craft Fair.

• Shelter Island 10K run: Annually in June - one of the most scenic races in the country
• Shelter Island Fireworks: Annually in July - mission to continue as an island tradition
• Shelter Island Art Show and Craft Fair: Annually in August - To promote local business and talent.

Go Kayaking On Shelter Island

Kayak tours on Shelter Island are fun for everyone and provide a glimpse into the island's nature experienced from the water. Visitors can head out either on a solo ride, or a doubles ride, or with a guide on a guided tour, explore the breathtaking Mashomack Preserve, or head into the nearby West Neck Creek.

For those who've never tried this activity before, it is important to know a few techniques and what to pack for kayaking before starting off, although the tour organizer will be able to help in the prepping for the excursion.

• Guided Tours: $60 per adult / $30 per child under 12 (2 hour tour)
• Kayak rentals for singles: 2 hours - $30, 4 hours - $45, All day $60
• Kayak rentals for double: 2 hours - $50, 4 hours - $70, All day $90

Relax At One Of The Many Amazing Shelter Island Hotels

Staying on Shelter Island can be expensive. The old-world charm has remained with recently renovated properties, and the premium price of hotels is intact. There are few hotels on the island, and the bookings start at around $200 a night.

The Ram’s Head Inn is a charming, historic hotel. The inn is where to stay on Shelter Island for a quintessential summer getaway that brings people back to the simple life. Situated on the waterfront on 4.5 elegantly landscaped acres, the Ram’s Head Inn is just a short walk from the beach.

Shelter Island provides an idyllic setting for some absolute relaxation in place of the life on the outside.

• Most hotels on Shelter Island are expensive , as they cater to an affluent section of society.
• The Rams Head Inn brings some sanity to the cost and experience while staying on Shelter Island.

Related: Best-Kept Long Island Secret: This Is How To Have The Perfect Cozy Day On Shelter Island In The Fall

Sample Unique Beers At The Shelter Island Craft Brewery

Only a short while back, Long Island could boast only one brewery, but now there are more than 50. Located in the town center of Shelter Island and started in 2015, it's easy to find Shelter Island Craft Brewery .

This New York State-certified farm brewery creates interesting and atypical beers using honey, apples, beach plums, spices, and Shelter Island scallops. The brewery features a tasting room as well as outdoor seating.

• Location: 55 N Ferry Rd, Shelter Island, NY 11964
• Timing & Schedule: Sunday-Monday, Friday - Saturday | 12:00 p.m. - 7:00 p.m.

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Unwind This Summer: A List of Long Island Wine Tours

If you are looking for a perfect weekend activity on Long Island this summer, consider exploring the region’s vibrant wine culture. Long Island has over 60 vineyards and numerous companies offer winery tours with tastings for both large and small groups to enjoy. 

North Fork Wine Tours 

714 Main St., Greenport, NY 11944 

[email protected] 

631-723-0505 

Long Island North Fork Wine Tours offers an opulent escape into the heart of Long Island’s wine country, with a personalized touch for every group size. Packages start at $130 per person and tours are available 7 days a week. All tours spend four to five hours at the vineyards, ensuring ample time to savor the flavors. Enjoy tastings included at three award winning vineyards, immersing yourself in the region’s rich wine culture. The North Fork Wine Tour Package on the Mercedes Limo Sprinter Bus is perfect for groups of 8-14 people, or indulge in the Premium Long Island Limo Party Bus package, designed for groups of 15-50. Lunch can also be provided for an additional fee of $14 per person. Weekday specials starting at $115 per person are also available. 

New Vine Wine Tours 

2284 Bridge Ln, Cutchogue, NY 11935 

631-409-8687 

New Vine Wine Tours is a family owned business that offers three different unique experiences for customers. The first option is the All-Inclusive Experience which includes visits to three select wineries, breweries, or distilleries, with tastings and reservations included. Indulge in a gourmet lunch at the second stop, served at a reserved table for your group. The next option is the Wine & Dine Experience. This package includes visits to two select wineries, breweries, or distilleries, with tastings and reservations arranged at both locations. Indulge in a sumptuous cheese platter at the first stop, followed by a three-course meal with a glass of house wine or beer at the Touch of Venice restaurant as the grand finale. The final option is the Do-It-Yourself Experience which includes only the vehicle and driver and you make all your own winery reservations. Pricing varies based on pickup location, party size, and vehicle selection. 

LI Wine Divas 

631-260-1830 

LI WIne Divas offers eight different wine tour packages depending on your number of guests. All packages are 7 and a half hours long and include stops at three Long Island wineries as well as a stop at Briermere Farms. Prices begin at $100 per person for large groups. Prices include transportation, vineyard admission and individual wine tasting. Box lunch is available for an additional $15 per person.

Tapped Enterprises 

14 Mary Ave, Ronkonkoma, NY 11779 

[email protected] 

631-913-3817 

Tapped Enterprises offers a variety of wine tours all with different twists including the Extraordinary Palate Tour and the Paint and Sip Tour. The Extraordinary Palate Tour provides the perfect mix by visiting one brewery, one winery and one orchard. At the Paint and Sip Tour guests will begin with a painting class before embarking on their wine tasting journey. The Classic Wine Tour which includes visits and tastings at three different wineries is also always available. Call Tapped for pricing. Special discounts are available on select Sundays. 

East End Wine Tasting Tours 

[email protected] 

631-366-6397 

East End Wine Tasting Tours offers diverse and customizable wine tour packages on Long Island, catering to various preferences and group sizes. Enjoy visits to premium wineries such as Mattebella and Macari. For those seeking a more economical experience, options include Osprey’s Dominion and Duck Walk Vineyard. The tours feature flexible lunch arrangements, from boxed lunches to prix fixe meals at local restaurants, ensuring a tailored and memorable experience for every group. 

Elegant Wine Tours Of LI 

1836 NY-112, Medford, NY 11763 

[email protected] 

631-345-9463 

Elegant Wine Tours of Long Island offers a variety of packages tailored to different group sizes and preferences. The Chardonnay Package caters to parties of 10-30 with a 7-hour tour via luxury party bus, visiting 2 wineries with samplings, and includes a light lunch for $150 per person. The Cabernet Package is designed for parties of 8-9, featuring a 7-hour tour in a luxury limousine, visiting 3 wineries, and includes a light lunch for $150 per person. The Chianti Package is perfect for smaller groups of 4-7, offering a 7-hour tour in a luxury limousine, visiting 3 wineries, with a light lunch included for $170 per person. For couples, the Riesling Package provides a 6-hour tour in a private executive towncar, visiting 3 wineries, for $470 per pair, with an optional limo upgrade for an additional $100. Lastly, the Zinfandel Package accommodates large groups of 11-57, with a 7-hour tour via luxury mini-coach or coach bus, visiting 2 wineries, and includes a light lunch for $125 per person.

Hamptons Wine Tours 

29 Laurel Ave Riverhead NY 11901 

E-mail: [email protected] 

631- 594-9017 

Hamptons Wine Tours offers a variety of wine tour packages. Group tours are available for those looking to meet new people and private tours are available for a more personal experience as well. The basic Wine Tour Package allows you to choose a vehicle and driver and you plan your own itinerary choosing from a selected list of wineries. The HWT Package includes a luxury car and driver, a visit to 2-3 wineries, 2-5 tastings at each winery and lunch for an additional charge. The final package is the HWT VIP Package which allows you to customize your own wine tour. 

Long Island Winery Limo 

215 Merrick Ave, Merrick, NY 11566 

[email protected] 

631-973-0000 

Long Island Winery Limo offers wine tasting packages in different price ranges including their Economical Party Wine Tasting Package, their Mid Range Wine Tasting Package and Premium Long Island Wine Tasting Package. Call Long Island Winery LImo for pricing information.

About the Author

Michael Malaszczyk

Michael Malaszczyk is the Digital Editor of the Long Island Press.

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