What to do in Shelter Island, NY

Activities, attractions and tours

Visit Shelter Island

Types of activities

Where to stay

Shelter Island travel guide

Houses along the bay in Saltaire, on Fire Island, New York

sailing in greenport long island new york Shelter Island coast landscape

his breathtaking drone shot captures the serene beauty of Southold in The Hamptons, New York. As the sun sets, it casts a golden glow over the lush landscapes and the expansive waters of Peconic Bay.

Shelter Island Attractions

Let Expedia help you to experience the best that Shelter Island has to offer! If you’re planning a trip to Shelter Island, we can provide you with a list of the top sightseeing attractions, as well as helping you to find unmissable activities. Whether you’re travelling to Shelter Island with your family, planning a romantic trip with your loved one, or visiting on business, we’ll make it easy to plan an unforgettable holiday that checks all the boxes.

Places of interest in Shelter Island

Shelter Island is crammed with must-see places to visit and things to do. We can help you decide where to stay in Shelter Island, and make it a breeze to explore Shelter Island and the surrounding areas with our guides on where to go, what to see and when to see it. No matter how long your stay, it’s easy to find places of interest in Shelter Island to make sure that you enjoy your holiday to the fullest and don’t miss a thing. Leave the local knowledge to us and leave the hassle behind.

If you’re planning a visit to Shelter Island, why not check out our handy guides to places of interest in the area? You can browse lists of things to do, learn about the most popular attractions, and get help with planning the details of your trip. Expedia makes it easy for you to check out all the top sights in Shelter Island.

Shelter Island attractions

Shelter Island has something for everyone, so whether you’re planning to get active on a summer holiday, put a spring in your step with a romantic rendezvous, or pamper yourself with a leisurely winter trip, you’ll find plenty of attractions in Shelter Island to keep you entertained. Expedia makes it easy to book your flight, hotel and rental car in advance, making for hassle-free travel and freeing you up to explore the sights of Shelter Island.

Looking for things to do in Shelter Island can be time-consuming, but we can take the hassle out of planning your holiday. Whether you’re looking to get active in the great outdoors, sample the cuisine of Shelter Island or catch up with the vibrant local culture, our guides to Shelter Island attractions ensure that you’ll have a successful trip, whatever the season. Happy trails!

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Recommended things to do in Shelter Island

Number of things to do	9
Cheapest thing to do on Expedia	Private Luxury Wine Tours of Long Island Pindar Winery: £133
Top 5 things to do	Private Beach Fire Montauk Half-Day Private Long Island Wine Tour Experience Private Holiday Photoshoot with Photographer in The Hamptons Long Island Winery Tour Private Luxury Wine Tours of Long Island Pindar Winery
Half-day tours	Private Beach Fire Montauk Private Holiday Photoshoot with Photographer in The Hamptons Private Holiday Photoshoot with Photographer The Hamptons
With kids	Private Beach Fire Montauk Private Holiday Photoshoot with Photographer in The Hamptons Private Holiday Photoshoot with Photographer The Hamptons

What to do in Shelter Island

Popular places to visit

Shell Beach

Why not spend a care-free afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.

Man watching sailboat on Long Island Sound

Wades Beach

Why not spend a care-free afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.

Gardiner's Bay Country Club

Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries.

Mashomack Preserve

Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area.

Havens House

You can spend an afternoon studying the exhibits at Havens House during your travels in Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.

Shelter Island Whale's Tail

You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area.

Shelter Island Historical Society

You can spend time browsing the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums.

Menhadden Lane Beach

Why not spend a care-free afternoon at Menhadden Lane Beach during your travels in Shelter Island Heights?

Explore areas of Shelter Island

Welcome To The Beach. Driftwood beach hut with handwritten welcome sign. Port Crescent State Park. Port Austin, Michigan.

Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Sunset Beach and Mashomack Preserve.

Center console boat on Long Island, NY. Photographed by drone.

Silver Beach

While Silver Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Crescent Beach.

A sweeping view of the natural beauty at Mashomack Preserve on Shelter Island which is situated between the North and South Forks of Long Island, New York.

Coecles Harbor

While Coecles Harbor isn't home to many top sights, Gardiner's Bay Country Club and Mashomack Preserve are some notable places to visit nearby.

view of wetland from the Marine Park Salt Marsh Nature Trail in brooklyn, new york (with gil hodges bridge to the rockaways int he background) cloud reflections in bay, water

Hay Beach

When in Hay Beach, you can plan a visit to Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.

Aerial Views of Mamaroneck, New Rochelle, and Larchmont

Shorewood

While Shorewood may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Mashomack Preserve and Sunset Beach.

Montclair Colony

If you're looking for some top things to see and do in Montclair Colony and surrounding area, you can visit Sunset Beach and Crescent Beach.

Looking for fun things to do nearby? Check things to do near me to find and book the best things to do, fun activities, and top attractions wherever you happen to be.

Day trip destinations from Shelter Island

East Hampton

Sag Harbor

East Marion

Northwest Harbor

Frequently asked questions

Is Shelter Island worth visiting?

From shopping to outdoor pursuits and history, there are plenty of fun things to do in Shelter Island. Make sure to discover the area's mix of cool attractions, local charm and culture.

How do I spend a day in Shelter Island?

Begin your day with a visit to 67 Steps Beach and Crescent Beach. Then, tour other parts of Shelter Island for local dining and some souvenir shopping.

What is the top tourist attraction in Shelter Island?

Don't leave without visiting Wolffer Estates Vineyard, ranked the top tourist attraction in Shelter Island.

Is three days enough to stay in Shelter Island?

Book a trip to Shelter Island for three days and you'll have enough time to tick off its most popular sights and get a taste for the local vibe. For the chance to visit highlights in nearby areas and get off the beaten path, consider staying for up to 10 days.

Is Shelter Island a walkable city?

Some key attractions in Shelter Island, such as Crescent Beach and Wades Beach, are within walking distance. You can also visit several of the city's popular neighbourhoods on foot. Only 5 kms (3 miles) from the city centre of Shelter Island is Greenport West and The Heights is 2 kms (1 mile) away.

What are some activities to do in Shelter Island with kids?

Deciding what to do in Shelter Island with kids has never been so easy. Whether you're travelling with little ones or teenagers, there's no shortage of family-friendly sights and activities to keep everyone entertained here.

What to do in Shelter Island for adults?

Whether you're a culture enthusiast, food connoisseur or adventure seeker, there are loads of things to do in Shelter Island for adults including Wolffer Estates Vineyard and Peconic Bay Winery.

Are there free things to do in Shelter Island?

From visiting parks to wandering around vibrant neighbourhoods, it's a breeze to find free things to do in Shelter Island. If you're stuck for ideas, get some recommendations from a local tour guide. 67 Steps Beach is a great spot for anyone wanting to save on their travelling adventures.