Top Sailing Spots to Explore on a Sailo Shelter Island Boat Rental


Nestled between the north and south fork of Long Island, Shelter Island is a quiet getaway from the crowded Hamptons. About two and half hours from New York City, the small island is only accessible by private boat or ferry. This peaceful island boasts Victorian houses dotting the island that date back to the whaling period on Long Island. With plenty of calm bays to explore on your Shelter Island boat rental, we put together the best places to eat and sail on the island. 


Pick up Croissants at Marie Eiffel Market

Before you embark on your journey on a Shetler Island boat rental, head to Marie Eiffel Market for a cup of coffee and essentials for the day. On the north side of Shelter Island overlooking the serene water, this market offers local and organic bakery items, breakfast and lunch sandwiches, fresh produce, beer and speciality items.


Start the day with an iced-coffee and their infamous croissant breakfast sandwich before heading to your Shelter Island boat rental.  


Sail Around Shelter Island 

For the adventurous sailor, you can embark on a journey around the entirety of Shelter Island on a boat rental.


With a circumference of 20 miles, sailing around the island is challenging yet serene. Hoist the mainsail, pull in the jib lines and prepare the crew to pass through Gardiners Bay, the Peconic River and the Shelter Island Sound. Start your adventure on the south fork of Long Island in Sag Harbor where you will pass the luxury yachts of the rich and famous. Make way around the Cedar Point Lighthouse, a house-like structure situated on a tip of land, into Gardiners Bay. Sail around the north side of the island and spy Greenport, the north fork of Long Island, in the distance. Head back to Sag Harbor as the sun starts to set. If you happen to be sailing on a Wednesday night, you will catch the colorful spinnakers of a local regatta in the distance. 


Enjoy Local Seafood at SALT

A day of pulling lines, suntanning and swan diving into the sea can build up an appetite! For a delectable meal or afternoon cocktail, make way to SALT Waterfront Bar & Grill.


Located on the south side of Shelter Island, dock your boat rental in the marina where the restaurant is located. Step off your boat and enjoy dinner on the dock overlooking the boats or take dinner to-go and eat on the boat. Dig into fresh fish tacos and other local delights. In true sailor form, sip a dark & stormy or whale killer. 


Anchor at the Infamous Sunset Beach

Following a delightful afternoon of sailing on your Shelter Island boat rental, head to the northwest side of Shelter Island to Sunset Beach. Drop anchor in the calm and protected bays for the perfect vantage point to watch the sun go down. Sip a glass of wine as you watch the skies fade from blue to pale pink and enjoy the last rays of the day’s warmth as you have cannonball contests with your sailing crew. If you have paddle boards or kayaks, the wind will start dying down and sunset is the perfect time to wade through the water.


If you’d like to get something to eat or drink, head to the chic hotel and restaurant onshore. 


Hike at Mashomack

After a half-day of sailing on your Shelter Island boat rental, head to Mashomack Preserve for an afternoon of hiking. As part of Nature Conservancy land, you are not able to anchor off of the preserve but you can access it by land. Spend the day exploring 11 miles of coastline at the park that means “where they go by water.”


Taking up about one-third of Shelter Island, Mashomack Preserve has plentiful coastline, forests and creeks to explore.