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Shelter Island

Shelter Island, NY, USA

Shelter Island

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Shelter Island

Shelter Island is a chill spot for anyone looking for a laid-back getaway. You can kick back on the beach, hit up some cute cafes, and explore the island's natural beauty. It's the perfect place to escape the city for a bit and recharge your batteries.

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Recommendations

Outdoor4.8/5

Mashomack Preserve

Welcome to Mashomack Preserve in Shelter Island, NY! This enchanting wildlife sanctuary is a hidden gem for adventurers and nature lovers. With over 2,000 acres of lush forests, wetlands, and picturesque shorelines, get ready for epic hikes, birdwatching, and kayaking. Don't forget your camera – you never know when you'll spot a majestic bald eagle or a mischievous raccoon!

Landmark4.5/5

Sylvester Manor Educational Farm

Nestled on Shelter Island, the idyllic Sylvester Manor Educational Farm is a captivating haven for curious souls. Dive into an immersive experience where history, agriculture, and sustainable practices come alive. Explore the lush grounds, join a farm tour, or participate in workshops. Unleash your inner farmer and embrace the vibrant spirit of this hidden gem.

Landmark5/5

Piccozzi's Bicycle Rental and Repair

Looking for a wheely good time on Shelter Island? Look no further than Piccozzi's Bicycle Rental and Repair! Located at 175 N Ferry Rd, their friendly team will hook you up with stylish bikes to explore the scenic island. Cruise along the stunning coastline, hit the trails, or simply pedal your way to fun. Let the adventures begin!

Transport4.7/5

Klenawicus Airfield

Welcome to Klenawicus Airfield, a hidden gem nestled in the stunning Shelter Island, NY! This aviation paradise offers breathtaking aerial views, thrilling flights, and a friendly atmosphere. Perfect for adventure seekers and aviation enthusiasts alike, you'll find knowledgeable staff, well-maintained aircraft, and top-notch flying experiences. Unleash your inner pilot and soar across the picturesque landscapes of Shelter Island with Klenawicus Airfield!

Culture4.8/5

Shelter Island History Museum

The Shelter Island Historical Society is a must-visit spot for history buffs and curious travelers alike! Located at 16 S Ferry Rd, Shelter Island, NY, this place is a treasure trove of fascinating stories. Dive into the past and discover the island's rich heritage through unique exhibits, interactive displays, and walking tours. Get ready to go on a journey through time!

Landmark4.8/5

Kayak Shelter Island

Nestled in the quaint Shelter Island, Kayak Shelter Island is your ticket to aquatic adventures! With a prime location at 80 Burns Rd, this hidden gem offers a wide array of kayaking experiences. Explore stunning coastlines, spot local wildlife, and soak up the island vibes. Whether you're a pro or a curious traveler, this is the ultimate spot for some wet and wild fun!

Landmark4.7/5

Gardiner's Bay Country Club

Welcome to the breathtaking Gardiner's Bay Country Club in Shelter Island, NY! This hidden gem offers the perfect getaway for golf enthusiasts. Swing your way through picturesque landscapes, surrounded by stunning bay views. With impeccable greens and a challenging course, it's a golfer's paradise. Don't forget to soak up the sun on their private beach after a victorious round. Ready for the ultimate golfing adventure? Look no further!

Landmark4.7/5

Coecles Harbor Marina & Boatyard

Welcome to Coecles Harbor Marina & Boatyard! Located in the heart of Shelter Island, NY, this place is a dream come true for water lovers. With stunning views, top-notch amenities, and friendly staff, your sailing adventure awaits. Dock your vessel or get some repairs done at the boatyard. Whether you're a seasoned sailor or a curious traveler, Coecles Harbor is here to make your waterfront dreams come true!

Eat$$4.7/5

The Eccentric Bagel

Nestled on picturesque Shelter Island, The Eccentric Bagel serves up bagels like no other! Step into this charming spot and savor whimsical flavors, from classic everything to inventive seasonal specials. With a cozy vibe and friendly staff, it’s the perfect pit stop for your morning caffeine fix or a leisurely brunch. Don’t miss their creamy schmears—pure bagel bliss awaits!

Outdoor1/5

Bridge Street Volunteer Park

Get your hands dirty at Bridge Street Volunteer Park in Shelter Island Heights! This community hub offers a chance to give back through gardening, clean-up projects, and more. Located at 212 Bridge St, it's the perfect spot to connect with locals and make a positive impact while exploring the charming town of Shelter Island.

Eat$$$$4.6/5

Vine Street Café

Welcome to Vine Street Café, a charming culinary oasis nestled in Shelter Island, NY. With its bohemian vibe and innovative farm-to-table menu, it's a must-visit for food-loving wanderers. Indulge in their divine lobster bucatini or savor their seasonal cocktails while basking in the picturesque waterfront views. An unforgettable experience awaits you at Vine Street Café.

Eat4.3/5

Isola

Isola, located at 15 Grand Ave in Shelter Island Heights, NY, is a traveler's paradise! This charming spot offers a delightful mix of sun, sand, and relaxation. With its trendy shops, delicious seafood, and breathtaking views of the bay, Isola is the perfect destination to escape the everyday hustle and bustle. Come explore this slice of paradise and let the island vibes wash over you!

Eat$$$4/5

Marie Eiffel Market

Marie Eiffel Market is a vibrant foodie haven nestled on Shelter Island. This charming spot offers an exciting mix of locally sourced ingredients, artisanal products, and delectable bites. With its picturesque location and welcoming atmosphere, it's the perfect place to indulge in gourmet treats, grab a picnic for the beach, or simply soak up the island's culinary scene. Bon appétit!

Eat$$$4.4/5

Stars Cafe

Welcome to Stars Cafe! Located at 17 Grand Ave in charming Shelter Island Heights, NY, this cozy and vibrant spot offers a scrumptious array of global flavors to fuel your wanderlust. From delicious lattes to mouthwatering pastries, their friendly staff will transport you on a taste adventure. Don't miss their outdoor seating area for stunning island views. Bon appétit!

Eat4.2/5

Shelter Island Craft Brewery

Welcome to Shelter Island Craft Brewery, where beer lovers' dreams come true! Located at 55 N Ferry Rd, Shelter Island, NY, our brewery offers a fun and unique experience. Enjoy our diverse selection of handcrafted beers, from IPAs to stouts, all made with love and passion. Join us for a pint, relax in our vibrant atmosphere, and savor the taste of our amazing brews. Cheers to unforgettable moments!

Stays

Stay4.65/5

Shelter Island House

Nestled in the charming hamlet of Shelter Island Heights, Shelter Island House offers a delightful escape for wanderlusters seeking a rejuvenating getaway. With its picturesque surroundings, this vibrant bed and breakfast is the perfect spot to unwind, enjoy the cozy rooms, and savor a scrumptious breakfast. Don't forget to explore the island's captivating beaches and lively restaurants just steps away! Bon voyage!

Stay4.35/5

The Pridwin Hotel & Cottages

Get ready to sail into an island paradise at The Pridwin! Located at 81 Shore Rd, Shelter Island, NY, this seaside gem will have you grinning from ear to ear. With stunning views, cozy beachside rooms, and delicious seafood galore, you'll never want to leave. So come on over and let The Pridwin make your vacation dreams come true!

Stay$$$$4.1/5

Sunset Beach Hotel

Welcome to Sunset Beach Hotel, where the only thing hotter than the island's sunsets is the vibrant atmosphere! Located at 35 Shore Rd, Shelter Island Heights, NY, this beachfront oasis is the ultimate vacation spot. Enjoy our stylish rooms, private beach access, and mouthwatering seafood at the lively bar. Let the good times roll at Sunset Beach Hotel!

Things To Do
Provided byViator

4.9/5
12 h

Hamptons Private Day Trip from New York City

Visit the Hamptons on this private, full-day trip from New York City with a chauffeured minivan that accommodates up to six passengers. Enjoy the ride in comfort and style, then spend the day seeing some of the most expensive and luxurious residential properties in the USA, with beautiful mansions and estates that slope down to the ocean's edge. Explore the streets of small villages, quaint shops, boutiques, art galleries, cafes and of course visit a winery.  Highlights of the trip include lunch by the ocean's edge.

$1,299.00
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4.3/5
12 h

The Hamptons and Long Island Wineries Private Tour

On this private tour from New York City, your morning will be spent visiting the quintessential Hamptons Village of Southampton with its lovely shops, cafes, pristine beaches and ocean front mansions. Then on to Sag Harbor with its 18th Century New England-style homes, infamous yacht club, wind mill and Long Wharf.  Following a harbor-side lunch of locally harvested seafood, you will take a ferry to Shelter Island.  After a relaxing drive across the Island, a second ferry will be taken to the North Fork of Long Island - the third largest wine making region in North America with 29 wineries.  You will enjoy tastings at several different wineries, with a return to New York City early in the evening.  This will be a day to remember!

$1,299.00
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3.8/5

Hamptons, Sag Harbor & Outlet Shopping, 1-Day Tour from NYC

Discover the Hamptons - a clutch of affluent seaside towns on Long Island about 90 miles (140 kilometers) from Manhattan - without fretting about car rental, trains, or buses on this day trip from NYC. Explore charming coastal villages, including Southampton and 300-year-old Sag Harbor. Hear stories from a guide you might never learn otherwise, stop for a wine-tasting, and enjoy free time to bag bargains at Riverhead's Tanger Outlets.

$179.00
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8 h

Hamptons Insider Tour with Private Helicopter from Manhattan

Experience the magic of the Hamptons—long known as a playground for the rich and famous—with a private helicopter flight from Manhattan to East Hampton Airport. Upon arrival, meet your local concierge and enjoy a full day with a climate-controlled luxury vehicle at your disposal. Begin with a guided tour of Sag Harbor, exploring hidden gems and centuries of history, or opt for shopping in East Hampton and visits to local art galleries. Take in the coastal lifestyle with seaside dining, award-winning wines, and glimpses of iconic celebrity homes. Enjoy a gourmet lunch with champagne at an elegant restaurant, followed by a private wine tasting in Bridgehampton. The experience can also include a visit to a classic Hamptons estate and time at pristine Atlantic beaches stretching for miles. Return to East Hampton Airport for your helicopter flight back to Manhattan. Availability: year-round. Flight time: ~1 hour each way. Total duration: ~8 hours.

$28,900.00
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7 h

Guided Seaside Golf Excursion with Private Helicopter from NYC

Enjoy a luxury escape to Montauk with a private helicopter journey from Manhattan, blending coastal scenery, golf, and a guided tour of this iconic seaside destination. Take in stunning aerial views of Long Island’s coastline before landing at Montauk Airport, where a local concierge and luxury vehicle await. Begin with a relaxed lunch, then head to Montauk Downs Golf Course for a 9-hole round, complete with clubs, balls, and cart. Originally developed in 1927 and redesigned by Robert Trent Jones Sr., the course is known for its scenic layout and dynamic ocean winds. After golf, explore Montauk on a guided driving tour, including the historic Montauk Lighthouse and other coastal highlights. Return by helicopter to Manhattan, finishing with a breathtaking NYC skyline tour. Availability: June–September. Flight time: ~1 hour each way. Total duration: ~9 hours.

$34,000.00
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5 h

Hamptons Beach Picnic with Private Helicopter from Manhattan

Escape the city with a private helicopter journey from Manhattan to East Hampton for a curated Hamptons luxury picnic experience. Enjoy scenic aerial views of Long Island’s coastline before landing at East Hampton Airport, where a private chauffeur will escort you to an exclusive beachside location. A beautifully styled picnic awaits, set against the Atlantic Ocean with elegant blankets, plush pillows, fresh flowers, and curated décor. Savor a fully catered gourmet spread with your preferred food and beverages, served on real china and glassware, while a dedicated attendant ensures every detail is flawless. After two hours of oceanside relaxation, return to the airport for your helicopter flight back to Manhattan, complete with a breathtaking NYC skyline tour. Availability: May–September. Flight time: ~1 hour each way. Total duration: ~4 hours.

$23,200.00
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10 h

Private Tour Hamptons from New York City

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to the heart of the city. Upon your arrival, meet your seasoned tour guide, ready to lead you on an enchanting tour of New York City. Discover the awe-inspiring allure of Southampton, marvel at the grandeur of Sag Harbor, and capture iconic moments at landmarks like Wolffer Estate Vineyard, East Hampton, Montauk, and many more. Our excursions are meticulously designed schedule. We'll greet you directly at the hotel and ensure you return with ample time to relax and relish your day.

$1,763.54
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10 h

Private Hamptons Coastal Escape from NYC

Swap Manhattan’s buzz for the Hamptons’ relaxed elegance on a 10-hour private ride through Long Island’s scenic towns and beaches. Enjoy hotel pickup and drop-off with a professional, English-speaking driver, and customize stops to suit your preferences. Begin in Southampton Village, exploring its tree-lined streets, boutiques, and galleries. Stroll along the pristine sands of Coopers Beach, then head to historic Sag Harbor with its charming marina and inviting cafés. Conclude at East Hampton Main Beach, taking in sweeping ocean views before your return to the city.

$699.54
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Private Hamptons and Montauk Tour from NYC with Hotel Pickup

Explore the luxurious Hamptons in a private Suburban or Escalade with an expert guide and dedicated driver. Discover the charming towns of Southampton, Sag Harbor, and Montauk, each with a distinct character and vibrant local energy. Pass by iconic celebrity homes and grand oceanfront estates that define the Hamptons lifestyle. Soak in the breathtaking Atlantic coastline as you make your way east toward the tip of Long Island. - Montauk Lighthouse visit - one of America's oldest and most iconic - Visit Southampton, Sag Harbor, and Montauk's charming boutiques and waterfront - Scenic beach stops along the Atlantic coastline - Wine tasting at a selected Hamptons winery - Fresh seafood lunch in Montauk harbor (own expense)

$1,162.00
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8 h 30 mins

Discover The Hamptons: A Self-Guided Tour

Discover the legendary Hamptons on this self-guided tour through the oceanfront villages along the South Fork of Long Island. For centuries, these shores have drawn artists, writers, and presidents, yet the Hamptons remain rooted in a quieter history of Shinnecock native peoples, settlers, and whalers. Begin in Southampton, where white-columned estates line lanes, then drive east through farm stands and vineyards between the glamorous towns. Explore Sag Harbor's whaling heritage, stroll the tree-canopied main street of East Hampton where windmills from the 1600s still stand, and continue to wild Montauk, where a lighthouse has guarded the Atlantic since George Washington authorized its construction in 1796. Along the way, encounter world-class beaches, art museums, and nature preserves that make the Hamptons far more than a celebrity playground. This tour reveals the authentic character beneath the glitz — a place shaped by the sea, the land, and 4 centuries of American stories.

$1.12
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5/5
5 h

Private Guided Wine Country Bike Tour in Mattituck

Nature Abounds on this 4.5-Hour Wine Country Bike Tour. An excellent way to see Long Island's Wine Country here on the North Fork. Take in beautiful views on this relaxing guided 4.5 Hour Tour cruise thru the scenic backroads of the charming north fork. On this backroads ride, nature abounds as seasoned guides lead you on winding roads up close to the tranquil Peconic Bay. Choose between 12, 14.5, 16, or 19 Mile routes...your preference. This tour has the ability to customize your experience. Different routes will offer different vineyard stops. After booking we will contact you via phone to craft the perfect experience that YOU are looking for! Bike riding is mostly flat with a few rolling hills.

$249.00
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5/5
2 h

Sunday Brunch Sail in Greenport

You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see the East End of Long Island, and sailing aboard our unique schooner makes the experience extra special. Unlike private charters that are widely offered in the area, this ticketed sail allows you to get on the water at a more affordable price.

$175.00
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5/5

Half Day(AM) North Fork Private Wine & Food Tour by Local Expert

As local experts, we take the guesswork out of planning your visit to the North Fork of Long Island. We know which venues are the most memorable and which wines are most enjoyable. As a team of passionate locals, we have scoured the area to handpick the best vineyards, restaurants, and hidden gems that you won't find on your average tourist map or group tour. Our expert guides will accompany you every step of the way, providing insider knowledge and fascinating stories about the rich history of the North Fork. Our private slow tour is 100% customizable and is tailored to you and/or your group's interests. Our all-inclusive fee covers all activities, food/wine, gratuities, and transportation for a seamless and memorable experience. Rain or shine.

$439.00
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5/5

Private Luxury Wine Tours of Long Island Pindar Winery

Discover the beauty and flavor of Long Island's wine country on this private tour tailored for wine enthusiasts and nature lovers. Begin your day with a comfortable transfer from Hicksville LIRR Station to the picturesque East End, where the charming Pindar Vineyards awaits. Enjoy a guided tasting of handcrafted wines amidst a scenic backdrop, complemented by casual music and insights into the local winemaking heritage. An optional lunch at one of the wineries allows for relaxation and enjoyment of the stunning views & Visit to Raphael Vineyards & Lenz Winery . - Private tour perfect for wine enthusiasts and nature lovers - Guided tour & tastings at Pindar Vineyards - Visit to Raphael Vineyards & Lenz Winery - Comfortable transport provided from Hicksville LIRR Station

$198.00
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5/5

North Fork Full Day Private Wine & Food Tour by Local Expert

As local experts, we take the guess work out of planning your visit to the North Fork of Long Island. We know which venues are the most memorable and which wines are most enjoyable. As a team of passionate locals, we have scoured the area to handpick the best vineyards, restaurants, and hidden gems that you won't find on your average tourist map or group tour. Our expert guides will accompany you every step of the way, providing insider knowledge and fascinating stories about the rich history of the North Fork. Our private slow tour is 100% customizable and is tailored to you and/or your group's interests. Our all inclusive fee covers all activities, food/wine, gratuities, and transportation for a seamless and memorable experience. Rain or shine.

$579.00
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5/5
4 h 30 mins

Private Guided Wine Country Bike Tour For Two (Mattituck)

Nature Abounds on this 4.5 Hour Wine Country Bike Tour. An excellent way to see Long Island's Wine Country here on the North Fork. Take in beautiful views on this relaxing guided 4.5 Hour Tour cruise thru scenic backroads of the charming north fork. On this backroads ride, nature abounds as seasoned guides lead you on winding roads up close to the tranquil Peconic Bay. Choose between 12, 14.5, 16, or 19 Mile routes...your preference. This tour has the ability to customize your experience. Different routes will offer different vineyard stops. After booking we will contact you via phone to craft the perfect experience that YOU are looking for! Bike riding is mostly flat with a few rolling hills.

$405.00
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5/5
8 h

Full Day Private Long Island Wine Tours from New York City

Welcome to the ultimate East End Long Island Wine Adventure! Prepare to immerse yourself in a journey through the region's lush vineyards, picturesque landscapes, and a symphony of exquisite flavors awaiting at every turn. Our escapade 1st stop is at the Bridge Lane Tasting Room, nestled snugly in the heart of Long Island's esteemed wine country. Bridge Lane's award-winning wines awaits your discerning palate. From crisp whites to robust reds, each sip is a testament to the unwavering dedication and passion of the esteemed winemakers. But hold on to your glasses, for our adventure is far from over! Our next stop is the illustrious Pindar Winery, a veritable jewel of the East End. The Pindar estate emanates an aura of elegance and charm, offering a delightful selection of meticulously crafted wines awaits your exploration. Join us on this unforgettable wine tastings through the captivating landscapes of Long Island's East End.

$189.00
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5/5

Half Day(PM) North Fork Private Wine & Food Tour by Local Expert

As local experts, we take the guesswork out of planning your visit to the North Fork of Long Island. We know which venues are the most memorable and which wines are most enjoyable. As a team of passionate locals, we have scoured the area to handpick the best vineyards, restaurants, and hidden gems that you won't find on your average tourist map or group tour. Our expert guides will accompany you every step of the way, providing insider knowledge and fascinating stories about the rich history of the North Fork. Our private slow tour is 100% customizable and is tailored to you and/or your group's interests. Our all-inclusive fee covers all activities, food/wine, gratuities, and transportation for a seamless and memorable experience. Rain or shine.

$439.00
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5/5
12 h

Full-Day Luxury Long Island Private Winery Tour

Our Luxury Long Island wine tour is a truly one of a kind experience. Guests will be driven privately (only their group) in luxury, 5 star accommodations. They can sit back and relax with their group, sipping wine and taking in the beautiful scenery. Guests will also be able to watch their favorite tv show , stream the latest content or listen to their favorite songs all while traveling to the beautiful wineries. This experience is truly unique. A group of up to 12 can travel in luxury accommodations while taking in New York's beautiful scenery. The Sprinter includes lounge chairs, air conditioning/heat, refrigerator and television. Completely private.

$2,300.00
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4.9/5
6 h

NYC Bus Tour of Brooklyn, Bronx, Queens: Art, Food & Sports

This bus tour spans four of New York City’s boroughs, covering everything you need to see in one day with convenient and comfortable transportation. With your local guide, learn about Harlem’s African-American history at the Apollo Theater and the Hasidic Jewish community in Williamsburg. Elsewhere in the Bronx and Brooklyn, admire colorful street art. We’ll also stop by an empanada shop that locals swear by, worth adding to your NYC bucket list. We’ll stop at Flushing Meadow-Corona Park to see Citi Field and the giant Unisphere. And there's a stop for lunch in a popular foodie destination surrounded by street art. And don't forget the photo ops of the Manhattan skyline and Brooklyn Bridge as you learn what makes DUMBO special. Our tour winds down with a visit to Chinatown and Little Italy. If you want to explore more here, your guide has tips on where to eat and shop!

$49.00
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