Title: 10 TOP Things to Do in Shelter Island September 2025 | Expedia.ca [Shelter Island Travel Guide](https://expedia.ca/Shelter-Island.dx157359)[Hotels in Shelter Island](https://expedia.ca/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)[Flights to Shelter Island](https://expedia.ca/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)[Shelter Island Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)[Shelter Island Vacation Packages](https://expedia.ca/Shelter-Island.d157359.Destination-Travel-Guides) # What to do in Shelter Island, NY ## Activities, attractions and tours ## Visit Shelter Island Types of activities Where to stay [Shelter Island travel guide](https://expedia.ca/Shelter-Island.dx157359) ![Photo by tom owens](https://mediaim.expedia.com/destination/2/57db4dbbb841fe5852df8ed4b2f64ec5.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by tom owens](https://mediaim.expedia.com/destination/2/57db4dbbb841fe5852df8ed4b2f64ec5.jpg) ![Photo by Rich Barton](https://mediaim.expedia.com/destination/2/1263ceec78a2ea3b58ee516bf8c95425.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Rich Barton](https://mediaim.expedia.com/destination/2/1263ceec78a2ea3b58ee516bf8c95425.jpg) ## Shelter Island Attractions Let Expedia help you experience the best that Shelter Island has to offer! If you’re looking for fun itinerary ideas, 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 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. #### Activities and Tours Shelter Island is crammed with must-see places to visit and things to do. We can help you decide where to stay, and make it a breeze to explore 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 experience 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, 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. #### Shelter Island Attractions Expedia 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 to keep you entertained. In addition to scheduling local tours, booking reservations and scoring advance event tickets, Expedia makes it easy to book your flight, hotel and rental car in advance, all on one consolidated travel itinerary, making for hassle-free travel and freeing you up to explore the sights of Shelter Island. Looking for things to do 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 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. * * * Explore thousands of activities with **free cancellation and no added fees**. Design your experience with airport transfers, excursions, day tours & more. Get an insider's look in what to book before you travel. * * * ## Recommended things to do in Shelter Island | Number of things to do | 14 | | --- | --- | | Cheapest thing to do on Expedia | [Guided Farm and Wine Country Bike Tour in Mattituck NY](https://expedia.ca/things-to-do/guided-farm-and-wine-country-bike-tour-in-mattituck-ny.a47629300.activity-details): CA $185 | | Top 5 things to do | - [Private Beach Fire Montauk](https://expedia.ca/things-to-do/private-beach-fire-at-town-line-beach.a4270665.activity-details) - [Mattituck New York Guided Farm and Wine Country Bike Tour](https://expedia.ca/things-to-do/mattituck-new-york-guided-farm-and-wine-country-bike-tour.a681055.activity-details) - [The Hamptons, Sag Harbour & Outlet Shopping Day Trip from NYC](https://expedia.ca/things-to-do/the-hamptons-sag-harbour-outlet-shopping-day-trip-from-nyc.a330552.activity-details) - [Private Professional Photoshoot in The Hamptons](https://expedia.ca/things-to-do/private-professional-photoshoot-in-the-hamptons.a48935201.activity-details) - [Half-Day Private Long Island Wine Tour Experience](https://expedia.ca/things-to-do/half-day-private-long-island-wine-tour-experience.a47265708.activity-details) | | Half-day tours | - [Private Beach Fire Montauk](https://expedia.ca/things-to-do/private-beach-fire-at-town-line-beach.a4270665.activity-details) - [Private Professional Photoshoot in The Hamptons](https://expedia.ca/things-to-do/private-professional-photoshoot-in-the-hamptons.a48935201.activity-details) - [Sagaponack Sunset Electric Bike Tour](https://expedia.ca/things-to-do/sagaponack-sunset-electric-bike-tour.a4488775.activity-details) | | With kids | - [Private Beach Fire Montauk](https://expedia.ca/things-to-do/private-beach-fire-at-town-line-beach.a4270665.activity-details) - [Private Guided Wine Country Bike Tour in Mattituck](https://expedia.ca/things-to-do/private-guided-wine-country-bike-tour-in-mattituck.a46206483.activity-details) | ## What to do in Shelter Island * * * ### Discover the most popular places to visit in Shelter Island #### 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. [](https://expedia.ca/Gardiners-Bay-Country-Club-Shelter-Island.d6282173.Vacation-Attraction) #### 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. [](https://expedia.ca/Shelter-Island-Whales-Tail-Shelter-Island.d553248621554204762.Vacation-Attraction) #### 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. [](https://expedia.ca/Mashomack-Preserve-Shelter-Island.d6224462.Vacation-Attraction) #### Wades Beach Why not spend a carefree afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums. [](https://expedia.ca/Wades-Beach-Shelter-Island.d553248621554204759.Vacation-Attraction) #### Shell Beach Why not spend a carefree afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums. [](https://expedia.ca/Shell-Beach-Shelter-Island.d553248621554204761.Vacation-Attraction) #### Shelter Island Historical Society You can spend time studying the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums. [](https://expedia.ca/Shelter-Island-Historical-Society-Shelter-Island.d553248635961235094.Vacation-Attraction) #### Havens House You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries. [](https://expedia.ca/Havens-House-Shelter-Island.d6232745.Vacation-Attraction) #### Menhadden Lane Beach Why not spend a carefree afternoon at Menhadden Lane Beach during your travels in Shelter Island Heights? [](https://expedia.ca/Menhadden-Lane-Beach-Shelter-Island-Heights.d553248621554204760.Vacation-Attraction) ### Explore areas of Shelter Island ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Menantic Creek If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Sunset Beach and Crescent Beach. [](https://expedia.ca/Shelter-Island-Menantic-Creek.dx553248635976481214) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Silver Beach While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach. [](https://expedia.ca/Shelter-Island-Silver-Beach.dx553248635976481903) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Coecles Harbor When in Coecles Harbor, you can plan a visit to Gardiner's Bay Country Club and Mashomack Preserve, some noteworthy sights in the nearby area. [](https://expedia.ca/Shelter-Island-Coecles-Harbor.dx553248635976480820) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Hay Beach Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out. [](https://expedia.ca/Shelter-Island-Hay-Beach.dx553248635976470037) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Shorewood While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Mashomack Preserve and Sunset Beach. [](https://expedia.ca/Shelter-Island-Shorewood.dx553248635976481937) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Montclair Colony While Montclair Colony isn't home to many top sights, Sunset Beach and Crescent Beach are some notable places to visit nearby. [](https://expedia.ca/Shelter-Island-Montclair-Colony.dx553248635976473165) * * * Looking for fun things to do nearby? Check [things to do near me](https://www.expedia.ca/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 Main Beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/252000/252521-Long-Island.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### East Hampton [](https://expedia.ca/East-Hampton.dx1524) ![Sag Harbor](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/252000/252775-Sag-Harbor.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Sag Harbor [](https://expedia.ca/Sag-Harbor.dx154327) ![Photo by Benny Goh ](https://mediaim.expedia.com/destination/2/64a7a541b17dabdb743e9908dec5b467.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### East Marion [](https://expedia.ca/East-Marion.dx6069914) ![Photo by Nina Dinoff](https://mediaim.expedia.com/destination/2/9a9f855657c0f02d64549df7b59e54eb.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Greenport West [](https://expedia.ca/Greenport-West.dx553248635975876381) ## 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 kilometres from the city centre of Shelter Island is Greenport West and The Heights is 2 kilometres 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. > > > > - [Private Beach Fire Montauk](https://expedia.ca/things-to-do/private-beach-fire-at-town-line-beach.a4270665.activity-details) > - [Private Guided Wine Country Bike Tour in Mattituck](https://expedia.ca/things-to-do/private-guided-wine-country-bike-tour-in-mattituck.a46206483.activity-details) ### 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. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - [3 Star Hotels in Greenport](https://www.expedia.ca/3Star-Greenport-Hotels.s30-0-d110728.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Greenport](https://www.expedia.ca/5Star-Greenport-Hotels.s50-0-d110728.Travel-Guide-Filter-Hotels) - [Bay Point Hotels](https://www.expedia.ca/Bay-Point-Sag-Harbor-Hotels.0-n553248635976471151-0.Travel-Guide-Filter-Hotels) - [Coecles Harbor Hotels](https://www.expedia.ca/Coecles-Harbor-Shelter-Island-Hotels.0-n553248635976480820-0.Travel-Guide-Filter-Hotels) - [Hotels near Crescent Beach](https://www.expedia.ca/Crescent-Beach-Hotels.0-l553248621554204758-0.Travel-Guide-Filter-Hotels) - [Cottages in Dering Harbor](https://www.expedia.ca/Dering-Harbor-Cottages.d553248634998885605-aaCottages.Travel-Guide-Accommodation) - 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