Things to do

"Life is short and summers are shorter, go have fun and make magical memories."

-Author Unknown

Sunset Beach, Shelter Island

This unique restaurant with award-winning cuisine is uniquely built around a large, majestic tree. Enjoy a lively bar scene and sip on the best mojitos you've ever had. This venue is Long Island’s best kept secret and now can be yours to enjoy. You can imagine yourself on the French Riviera at St. Tropez while actually being on Shelter Island. We suggest you stay to watch the sunset on the top deck, an awesome experience. The beach includes paddle board rentals, volleyball, luxurious massages and more. It is the perfect getaway for couples, and families. This is a must-see while in the Hamptons.

Sag Harbor Charters

If you’re familiar with the Hamptons’ upscale scene, you’ll soon realize that, though it’s in the Hamptons, Sag Harbor has a unique vibe of it's own. Located on the South Fork’s north coast, this historic hamlet has a strong maritime essence that stems from its history as a whaling port. The first white settlers arrived in the late 1600s. They learned about whaling from the resident Native Americans, and started sending out whaleboats in the mid-1700s. By the time the industry hit its peak in the mid-1800s, Sag Harbor had become one of the world’s busiest ports. Take some time to walk along historic Main Street, lined with boutiques, galleries, and great restaurants. This leads to the wharf, which for centuries has served as the heart of this community. During colonial times, tall ships from around the world would drop anchor here. Today it is the luxurious sailboats and yachts that line the marina and bay. Don't be surprised if you see the Mayor of Margaritaville, Jimmy Buffet, whose yacht is often moored there along with boats owned by many of the celebrities who call this area their summer playground. There is a wonderful playhouse on the wharf where Hollywood celebrities often perform or attend the shows. Thanks to careful preservation, much of Sag Harbor’s 18th- and 19th-century architecture remains intact, including Greek Revival houses once owned by whaling captains, and early-colonists, along with Victorian homes built for wealthy industrialists. Start your visit down by the harbor at the windmill that houses the visitor center. The volunteers there will answer your questions and inspire you to truly appreciate and enjoy this wonderful seaport. You can count on Hamptons Boat Rentals to take you to the most breathtaking areas on Long Island.

SALT Waterfront Bar and Grill, Shelter Island

Fresh seafood, delicious frozen drinks and a full menu are available at "SALT" on beautiful West Neck Creek, Shelter Island – Live music and friendly people at the famous Shipwreck Bar. Celebrities such as Jimmy Fallon frequent this waterfront gem (see pic). It boasts Shelter Island’s only wine tasting room – Getting there by Hamptons Boat Rentals is a the most fun way to go.

Greenport Boat Rentals

Located on the North Fork of Long Island is the charming, historic village of Greenport. Just a short ride from Shelter Island and the rest of the Hamptons, Hamptons Boat Rentals can take you there. Greenport is a quaint seaport where you can take a stroll around town, enjoy the shops, restaurants and even take a fun ride on an old fashion merry go round, located along the waterfront. Discovering this wonderful town through Hamptons Boat Rentals will convince you that you made a wise decision visiting there and will need to return for a longer stay next time. We recommend Claudio's Restaurant for delicious seafood and a casual beach bar vibe.

Kokomo's Restaurant & Beach Bar

Kokomo’s Restaurant is located right on Sound View Beach in Old Lyme, CT. We serve seafood, sandwiches and more with craft beers or specialty drinks. We offer a beautiful, waterfront dining experience. Kokomo’s menu celebrates the healthy and delicious summertime food of the French Riviera and coastal Italy. Many signature dishes return in 2019—moules mariniére, niçoise salad, bouillabaisse—supplemented by new additions for lunch and dinner from executive chef Edi Cungu.

Explore Kokomo's Restaurant

North Fork Long Island Wineries

When you visit the Long Island Wine Region, you share in the pride that we have for our people, our land and the culture that make us unique. A visit to the East End demonstrates the close, seasonal connection between land and table as wonderful local products are grown, picked, and harvested daily at the height of ripeness, perfectly complimenting our wines and other produce grown here. Allow us to take you by boat to the best Wine Country in proximity of NYC.

Navy Beach, Montauk

Navy Beach serves casual coastal cuisine in a laid back, family-friendly setting. Positioned on a 200-foot private beach, the restaurant offers prime seating on the beach and some of the best sunsets in the Hamptons. The restaurant features fresh seafood and locally-sourced produce, as well as a large variety of internationally-influenced menu items that change seasonally. Since opening in 2010, this restaurant has become a popular boating destination as well as a go-to place for connoisseurs of great wines, with one of the largest selections of rosé wines in the area.

Long Island Aquarium, Riverhead

Two great family attractions in one fin-tastic destination! This full-scale Aquarium and brand-new Exhibition Center features one of the largest all-living coral reef displays in this hemisphere; a 120,000-gallon shark tank, year-round sea lion shows, numerous touch tanks, and more than 100 exhibits and interactive experiences, including Shark Dive, Pirate Snorkel Adventure, Atlantis Explorer Tour Boat and Sea Lion Kiss. The exhibition center offers different shows through out the year. Fun for everyone! Let Hampton Boat Rentals take you there.

Shelter Island Estuary Tour

Just 80 miles east of the hustle and bustle that is New York City lays the unparalleled beauty and tranquility of Long Island’s East End and the Peconic Estuary. Dubbed one of the “Last Great Places” in the western hemisphere, the Peconic Estuary is situated between the north and south forks of Long Island. The watershed begins at Brookhaven National Lab with the headwaters of the Peconic River, spans the several bays from Flanders to Gardiners, and ends in Block Island Sound between Plum Island and Montauk Point. More than 125,000 land acres and 158,000 surface water acres are included in the Peconic Study Area. If you want a peaceful and natural tour to remind you that undisturbed nature still exists then sit back and enjoy the views.

Sunset Beach, Shelter Island Beach Massage

Nothing can be more relaxing than a 1 hour beach massage on beautiful Sunset Beach Shelter Island. Let yourself go and allow Hamptons Boat rental to bring you to Sunset beach where you will experience one of the best massages you have ever had. If you are looking to have the best massage of your life, then do what dozens of our guest do and treat yourself or your special loved one to a massage. Massages start at $65. Couple massages on the beach are also available. The prices are surprisingly low for our guests. We will take you by boat to Sunset Beach then just y lay down and let your masseuse perform magic on your back and do the rest. Create your most memorable day of the summer and allow us to book your massage.

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Shelter Island Paddle Boards

Shelter lsland, 27 square miles of beauty and tranquility. Located just 90 miles east of NYC allows for a quick getaway you will never forget. Vast tracts of protected wetlands, and nearly one-third of the island is preserved in a wild state. There are countless activities and places to see. Whether you're a veteran paddler, an explorer, or a beginner, paddle boarding on Shelter Island is a great activity. Venture Out is our point of contact. Boards can be delivered to any location to allow a close up exploration of Shelter Island marine life in the clear waterways, creeks and inlets without disturbing their habitats. Let Hamptons Boat Rentals bring you there.

Ram's Head Inn

Hidden on an island's island, atop a beautiful, waterfront hillside sits the chic and historic Rams Head Inn. With a private beach and Great Lawn the outdoor activities are endless; paddle boarding, bocce ball, hammock time and sunbathing just to name a few. But don't stop the enjoyment yet, inside this incredible venue, with 17 beautifully decorated rooms, is a Restaurant, Bar and Lounge offering delightful dishes and cocktails served with fresh produce from their garden, of which you can walk! Enjoy a bespoke wellness experience with resident Guru, Troy Mills, live music or partake in one of the many activities offered including Fireside Chats with renowned Authors, Oyster Shucking & Wine, Aquaculture Club and even Monday Trivia. The sunsets are famous from this picture perfect venue - so much so they offer private dinner in their beachfront pergola. This place is one for the memories, so much so you might just stay a while!