What to do and see in Hamptons, Long Island: The Best Boat Tours & Water Sports

February 19, 2022 Cedrick Jardin

The legendary Hamptons, a cluster of wealthy enclaves on Long Island’s South Fork, remains a celebrity summer playground, with splashy restaurants and nightclubs galore. But lovely beaches, fishing and kayaking attract off-the-A-list visitors, as well. Old money oozes throughout Southampton, while new wealth reigns in East Hampton. Montauk is a hit with fishermen and surfers. The Long Island Railroad travels the Hamptons in an hour. The Sag Harbor Whaling Museum and Montauk lighthouse are popular stops.
Restaurants in Hamptons

1. Sailing Montauk's Catamaran Mon Tiki

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5.0 based on 199 reviews

Sailing Montauk's Catamaran Mon Tiki

Sailing Montauk presents Mon Tiki Largo—a US Coast Guard Certified eco-conscious catamaran inspired by traditional Polynesian double-canoe designs. Come aboard for one of our daily scheduled sailing trips, or use your imagination to create your own special seafaring adventure. No experience is necessary, and all ages are welcome! Mon Tiki is the only US Coast Guard certified sailing vessel operating full-time in Montauk. We offer both "walk-on" daysailing and sunset cruise and private charters for groups of any size. Let's go sailing!

2. Sail Montauk

Excellent
98%
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5.0 based on 172 reviews

Sail Montauk

Step off the dock and onto one of our private sailboats for an exhilarating sail on the waters of Montauk. Take the tiller or just sit back and relax; we'll make your sailing experience one of a kind. Get a Taste of Sailing with our private 2 hour sails, or spend some more time on the water with a Sail & Swim package. Book a Private Lessons will help you fine tune your skills. If you're just looking to relax, come aboard for a private Sunset Sail with the best views in Montauk, perfect for sweethearts and groups of friends. No matter what your level of experience, create ever lasting memories when you Sail Montauk.

3. Sag Harbor Charters

Excellent
96%
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4%
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5.0 based on 185 reviews

Sag Harbor Charters

Wonderfull boat outings in the Hamptons. Sunset cruises, trips around Shelter Island. Lunch or dinner on the boat. Swimming and sightseeing by the hour. Confortable and safe. Plenty of shade and toilet on board. You are welcome to bring drinks and food aboard. Your captain will share his knowledge with you and your guests. Take in the beautifull bay and see the stately homes of the hamptons. I will take you to the greatest natural spots on the bay. All aboard!

4. Shelter Island Kayak

Excellent
92%
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8%
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5.0 based on 26 reviews

Shelter Island Kayak

Enjoy a serene paddling adventure exploring the unique natural beauty of Shelter Island’s calm, protected creeks and harbors. Escape from noise, traffic, and crowds—and find yourself surrounded by landscapes untouched by man. Explore the skies for osprey and hawks, watch egrets and turtles remarkably close-up along shore-lines, and observe fish and marine life in the clear waterways. Kayaking allows you to get closer to nature than almost any other form of sport or recreation. Kayaks are a great way to explore the Island in a green, or eco-friendly way. Paddling is extremely quiet, and allows you to enter Shelter Island’s incredible habitats, and leave them completely undisturbed. If you’ve been to Shelter Island before, or you are visiting for the first time, a trip by kayak offers a new perspective of a truly amazing place.

5. Sailacat Boat Charters

Excellent
98%
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5.0 based on 126 reviews

Sailacat Boat Charters

Sailacat offers private sailboat charters , boat rentals including sunset sails & catamaran cruises in the Hamptons, Sag Harbor and Bahamas. Enjoy a full or half day sail, sunset cruise or Yoga meditation Sail in the heart of the beautiful Hamptons. Join us for a fun filled catamaran sail aboard a beautiful ocean going Sailing cat. Bring lunch or we'll arrange catering for you. Sailacat is ideal for family get togethers, Birthdays, Honeymoons & Romantic Dinner cruises. We also offer Bareboat charters, Bahamas cruises and all inclusive Yoga Sail Retreats, ( with luxury accomodations ashore) . Saiilacat's spacious catamaran offers both fully shaded lounging, as well as sailing in full sun forward, on her ample foredeck, so all may enjoy the best the Hampton's has to offer in comfort & style. We look forward to sailing with you soon !

6. Weejack Charters

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5.0 based on 24 reviews

Weejack Charters

State-of-the-art fishing charter boat for friends, family, and corporate outings. Catch huge shark, bass, tuna or enjoy a tour of Montauk's beautiful waters and fabulous sunsets.

7. Double D Charters

Excellent
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5.0 based on 93 reviews

Double D Charters

Double D Charters specializes in fishing for all species in season. Striped Bass, Shark, Tuna, Fluke, Sea Bass you name it. Montauk is a town with a rich fishing heritage and a trip to Montauk without taking a fishing trip would be a mistake. Accommodating from 1-15 passengers.

8. Adventure Paddleboards & Kayaks

Excellent
95%
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5.0 based on 20 reviews

Adventure Paddleboards & Kayaks

Stand up Paddleboard Lessons,Rentals, Paddle Board Yoga/Fitness on the east End of long Island. Located on Shinnecock Bay in East Quogue NY at Dickers Waterside and Marina. Gourmet Food Truck open for lunch all summer, fresh squeezed juices and Live Music every Wednesday nights 6-10pm 6/18-9/10-2014 Check our website for more info!

9. American Beauty Cruises & Charters

Excellent
96%
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5.0 based on 27 reviews

American Beauty Cruises & Charters

We offer three types of Sag Harbor boat rides, rentals and charters. All three are top attractions on the East End of Long Island and the Hamptons. . 1 - Private boat charters for all occasions - bachelorette and birthday party boats, family and group reunions, camps, schools, etc. 2 - 90 Minute narrated, sightseeing boat rides. 3 - Two hour Sunset Cruise boat tour. Visit our website for schedules and to purchase advance tickets. We have one boat, the American Beauty II which is US Coast Guard inspected and approved to accept up to 33 passengers. We can handle your large group like few can. One of the most fun things to do in the Hamptons and Long Island. See our website for more details. Click on "INFO->Videos" to see tour videos and photos. See our website to view our COVID safety protocol.

10. Starlight Sailing Charters

Excellent
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5.0 based on 10 reviews

Starlight Sailing Charters

Sailhamptons has a wonderful time sailing with all types of private groups ranging in size from 2 - 41 guests. With our US Coast Guard Inspected schooner Luna (2-41 guests), we can accommodate all types of larger groups, from corporate events to family outings, bachelorette parties, birthdays and even just a nice afternoon out. Our second boat, the Luxury Sailing Yacht Starlight, is perfect for smaller groups (up to 12). Sailhamptons provides private luxury private day charters from Sag Harbor, Shelter Island, and the Hamptons. Our trips are fully crewed with experienced professional yachting and hospitality staff. Between a wonderful assortment of serving-ware cutlery and glasses on each of our boats, and water toys and paddle boards o deck, Sailhamptons is able to make any even perfect.

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