Matthew Breitenbach | September 18, 2021

Best Sailing Excursions from the Hamptons

The Hamptons are known for their glamorous mansions and affluent residents. However, these seaside communities also have some of the most exciting boat charters and gorgeous open waters in the United States. 

Whether you’re looking for an adventure on the sea or just want to relax and enjoy the scenery, these sailing excursions from the Hamptons are some of the best.

Sail Montauk

Credit: Sail Montauk

Cruise along the waters of Montauk on a private sailboat tour. A Certified Sailing School with the American Sailing Association, Sail Montauk provides private lessons for adults and kids as well as certification courses. Sail Montauk offers a wide range of trips, lessons, camps, and vacations with their U.S. Coast Guard licensed captains. 

If you already know how to sail, sailboats and inflatable boats are available to rent. Private sailing charters include a Taste of Sailing and Sunset Sail, where you can go on a typical charter while taking in the beautiful surroundings of the Hamptons. If you’re looking to let loose, the Sail & Swim trip features pool noodles and water guns, and the Flotilla Boat Party allows you to float multiple boats alongside each other. 

Sail Montauk offers a wide range of sailing school classes as well. Options include intro and 101 courses covering boat handling, sailing terminology, navigation rules and aids, safety gear and procedures, and important sailing knots. A Fleet Skipper Workshop is available for those with basic sailing knowledge, which orients guests on Sail Montauk’s rental fleet. If you have kids, there are summer camps and private lesson packages geared towards young sailors as well. 

Some of the most unique experiences that Sail Montauk offers, however, are its Caribbean Sailing Vacations. Go island-hopping in the British or U.S. Virgin Islands as you sail to a new tropical location every day. Participate in daytime activities like snorkeling and hiking, and enjoy local food and drinks in the evening. Both the Monohull and Catamaran sailboats boast luxurious, private accommodations on your sailing vacation to paradise. No matter what type of sailing charter you are looking for, Sail Montauk has got you covered.


Hop aboard what has been dubbed the AirBnb of boats. Sailo offers sailors a terrific choice of boats and yachts that they can rent to discover the Hamptons. Rent a private charter with the option of having either a captained boat or bareboat with no crew. Enjoy your time on the open sea with friends and family while sailing through the glamorous Hamptons. 

The Hamptons’ most sought-after charters and activities include sailing around Shelter Island, living the good life on a yacht, and indulging in watersports at Sag Harbor. 

Shelter Island lies in between the forks at the end of Long Island. Home to the marshy nature reserve of Mashomack Preserve, Shelter Island is a coastal town with several charming marinas, as well as quaint restaurants and shops. 

Charter a luxury yacht to get a taste of how the rich and famous spend their summers in the Hamptons. Dock and shop at high-end boutiques on the main street, or anchor in a cove and hang out on deck. If you’re seeking more of a thrill, take up watersports at the far eastern end of Long Island in the town of Sag Harbor. Try your hand at wakeboarding or waterskiing if you want a challenge or paddleboarding if you want to start slow. 

Regardless of which Hamptons experience you fancy, Sailo will match you to the boat that’s perfect for your sailing trip goals.

Viking Fleet

Credit: Viking Fleet

Sail on a first-class vessel while you go on a Fun Cruise, Whale Watching Trip, Fast Ferry Service, or Fishing Trip. Viking Fleet charters along the East Hampton Town of Montauk, New York. 

The fleet’s Fun Cruises include afternoon and sunset private charters that can accommodate up to 40 passengers. These boats have rooftop decks perfect for sunbathing or stargazing, as well as fully stocked bars. 

Viking Fleet’s most adventurous tour is its Whale Watching Trip. Be on the lookout for whales, dolphins, turtles, and seabirds on this thrilling five-hour charter. 

Viking Fleet also offers a Fast Ferry Service Ride for those who want to take a weekend trip to surrounding areas. Destinations to and from Montauk include Block Island, Rhode Island, and New London, Connecticut. 

Finally, Viking Fleet provides both inshore and offshore fishing trips. Try to hook a Jumbo Fluke or Knothead Sea Bass using the newest fish-finding technology equipped on these boats. Climb aboard one of Viking Fleet’s world-class sailboats to get up close to wildlife in their natural habitat, or to relax in style and take in the picturesque sights of the Hamptons.

East End Charters

Credit: East End Charters

Sail on flagship yachts as you partake in specialized day or overnight charters. East End Charters is composed of a highly-established fleet of ships that uphold U.S. Coast Guard regulations. Tours range from casual to luxury and can accommodate up to 41 passengers based on ship. 

Surprise is the name of East End Charters’ flagship yacht. Built back in 1967, this custom-built wooden yacht offers some of the most stable yet elegant charters in Eastern Long Island. Find peace on the water as you make your way into secluded beaches and harbors that most yachts are unable to access. Surprise has a spacious main cabin and deck, as well as a wide swim ladder for those who want to take a dip in the ocean. 

East End Charters also offers customized sailing trips for all types of celebrations and parties. Luna is a spectacular yacht upgraded with modern amenities perfect for any elegant occasion or lively getaway. Marlinspike is a lobster yacht on which passengers can bird watch, view lighthouses, or swim at the beach. 

Finally, Bluebell is a classic yacht that provides the ultimate local experience of seaside restaurants and state parks. Create a special moment aboard one of East End Charters’ seasoned and professional sailing yachts.

November Rain Charters

Partake in some of the best freshwater and saltwater fishing in the United States with America’s top-rated charter. Located in Montauk, November Rain Charters was named the 2020 Traveler’s Choice Winner by TripAdvisor and the 2020 Angler’s Choice Winner by Fishing Booker. 

Montauk has one of the largest recreational fishing fleets in New York, which is why you will find the sign “Fishing Capital of the World” at the village’s harbor. The charter’s boat, November Rain, can hold up to 20 passengers. The boat’s spacious cabin provides a smooth ride, especially as you travel deeper into the open sea. Other boat features include booth and bench seating, air conditioning and heat, a television, Bluetooth radio, a mini kitchen, and a bathroom. 

November Rain Charters offers both inshore and offshore fishing trips. Closer to the shore, you will find flounder, striped bass, porgy, and blackfish roaming. If you want to venture out a little further, you can catch tuna, mahi-mahi, shark, and marlin. Looking for a non-fishing trip? November Rain also provides sunset cruises so you can bask in the beauty of the Hamptons. Whether you’re looking to reel in some fish or cruise along the water, November Rain Charters will tailor the trip to meet your needs.

If you're looking for a bite to eat after your boating experience, check out the best waterfront restaurants in the Hamptons

Hamptons Luxury Real Estate

If you are interested in information regarding luxury homes for sale in the Hamptons, contact Matthew Breitenbach. Matthew comes from one of the most successful real estate families in the Hamptons. Known for providing first-class service and consultation, Matthew is considered the leader of a new generation in real estate. If you are seeking a leading luxury real estate experience, collaborate with the Breitenbach Advisory Team.


You can always learn more about the Breitenbach Real Estate Agents in Hamptons.


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