Long Island’s sailing scene delivers stunning coastal experiences with options for every budget. Based on decades of travel experience, the standout choices include private yacht charters from The Hamptons, Montauk, and Sag Harbor. The Hamptons-based charters ($2,390 for 10 people) earn top marks for their professional crews and well-maintained vessels. I’m particularly fond of Captain Steve’s NYC skyline tour ($475) – it’s thorough, expertly guided, and offers exceptional photo opportunities.
For value and flexibility, the Sag Harbor boat rentals (starting at £1,589.75) provide intimate experiences for small groups of 8. The Great South Bay yacht parties and Shelter Island sailing tours deserve special mention for combining local charm with seasoned maritime expertise.
Let’s explore the finest sailing tours Long Island has to offer.
Good To Know
- Private yacht charters in The Hamptons, Montauk, and Sag Harbor offer customizable 5-star rated experiences starting at $2,390 for up to 10 people.
- Boat or yacht rentals in Sag Harbor, The Hamptons, and Montauk provide flexible options starting from £1,589.75 for up to 8 people with free cancellation.
- Captain Steve’s sailing experience in Port Washington offers stunning views of Kings Point, City Island, and the NYC skyline for $475 up to 6 people.
- Private yacht parties in Great South Bay, Long Island, provide all-inclusive experiences with parking, fuel surcharge, and BYOB dinner.
- Wind Dancer Charters offer a half-day private sailing experience in Long Island for $958.64 up to 6 passengers, including yacht equipment and private transportation.
Private Yacht Charter in The Hamptons, Montauk or Sag Harbor
Chartering a private yacht in The Hamptons, Montauk, or Sag Harbor offers travelers an unparalleled opportunity to experience the beauty of Long Island’s coastline.
This service, recommended by 100% of travelers, provides a luxurious and personalized way to explore the region. With a 5.0 rating from 10 reviews, the private yacht charter includes fuel surcharge and a captain, ensuring a seamless and enjoyable experience.
Priced from $2,390.00 per group of up to 10 people, the service offers free cancellation and unlimited rescheduling up to 24 hours before the experience.
While not wheelchair accessible, the private tour allows travelers to customize their adventure and create lasting memories on the water.
Read our full review: Private Yacht Charter in The Hamptons, Montauk or Sag Harbor Review
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Boat or Yacht Rental in Sag Harbor, The Hamptons, or Monatauk
Boat or yacht rental in Sag Harbor, The Hamptons, or Montauk provides travelers with the freedom to explore Long Island’s picturesque coastline at their own pace.
Prices start from £1,589.75 per group (up to 8 people), allowing for a cost-effective way to enjoy a private sailing experience. Rentals offer free cancellation up to 24 hours in advance, and a reserve now, pay later option is available.
The meeting point is at 10 Wharf St, Sag Harbor, NY, and all necessary equipment is included. While not wheelchair accessible, most travelers can participate, and service animals are allowed.
With a 5-star rating across multiple platforms, this activity is a top choice for those seeking an unforgettable sailing adventure.
Read our full review: Boat or Yacht Rental in Sag Harbor, The Hamptons, or Monatauk Review
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Captain Steves Sailing Experience on Long Island
Captain Steve’s Sailing Experience on Long Island offers travelers a unique opportunity to explore the picturesque coastline from the comfort of a private sailing charter.
Located in Port Washington, NY, this 5-star rated excursion provides stunning views of the surrounding area, including Kings Point, City Island, Hart Island, and the New York City skyline.
With knowledgeable and friendly Captain Steve at the helm, guests can expect attentive service and engaging interaction throughout the tour.
While the experience isn’t recommended for those with certain medical conditions, the moderate fitness level required ensures a safe and enjoyable outing for most visitors.
Priced at $475 for up to 6 people, this private sailing tour is a must-try for anyone seeking a memorable adventure on Long Island’s waters.
Read our full review: Captain Steves Sailing Experience on Long Island Review
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Private Yacht Party on the Great South Bay of Long Island
A popular option for those seeking a private nautical adventure on Long Island’s picturesque Great South Bay is the yacht party offered by Long Island Private Yacht Charters.
The all-inclusive experience includes parking, fuel surcharge, bottled water, BYOB alcoholic beverages and dinner, as well as gratuities.
Passengers meet at the Patchogue location, where they’ll find the yacht under a big blue crane, and receive a free parking pass before setting sail.
The tour isn’t wheelchair accessible but stroller-friendly, and is located near public transportation.
Confirmation is provided upon booking, subject to availability.
Read our full review: Private Yacht Party on the Great South Bay of Long Island Review
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Half-Day Private Sailing in Sag Harbor and Shelter Island
Visitors seeking a unique nautical adventure on Long Island can embark on a half-day private sailing excursion with Wind Dancer Charters. The charter offers an intimate, group-only experience, accommodating up to 6 passengers.
At $958.64 per group, the tour includes use of the yacht’s equipment, bottled water, and private transportation to and from the launch point in Sag Harbor. Guests must arrive 15 minutes early and pay a $5 per person launch fee.
While not wheelchair accessible, the tour welcomes service animals and infants, with the latter sitting on laps.
With free cancellation up to 24 hours prior, this half-day sail is a flexible and exclusive way to explore the picturesque waters of Sag Harbor and Shelter Island.
Read our full review: Half-Day Private Sailing in Sag Harbor and Shelter Island Review
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Private Long Island Sound Sailing Experience
Nestled along the shores of Long Island Sound, the Private Long Island Sound Sailing Experience offers a unique opportunity for visitors to enjoy the breathtaking maritime scenery.
Passengers can embark on a private charter sailing journey, exploring Manhasset Bay, taking in views of multi-million-dollar mansions, and catching glimpses of the New York City skyline.
The experience includes sightseeing highlights like the Throgs Neck Bridge, Hart Island, and Steppingstone and Execution Rocks lighthouses.
Participants can actively engage in sailing or opt to anchor for lunch and swimming.
Ideal for celebrations, this charter caters to birthdays, anniversaries, and bachelorette parties.
The experience is available from May 2021 to July 2025, with operating hours catering to both weekdays and weekends.
Read our full review: Private Long Island Sound Sailing Experience Review
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Frequently Asked Questions
What Is the Minimum Group Size for a Private Yacht Charter?
The minimum group size for a private yacht charter typically ranges from 2 to 6 people, though some charters may accommodate larger groups. The exact minimum can vary depending on the yacht size and the charter company’s policies.
Can I Bring My Own Food and Drinks on a Yacht Rental?
Yes, most yacht rental companies allow guests to bring their own food and drinks on board. This can help save on catering costs and allow guests to enjoy their preferred refreshments during the sailing experience.
Do I Need Boating Experience to Charter a Private Sailing Tour?
No, you don’t need boating experience to charter a private sailing tour. Many sailing tour companies provide experienced captains and crew to guide you, so you can enjoy the scenic views without worrying about sailing the vessel.
Is There a Dress Code for a Private Yacht Party?
There’s generally no strict dress code for a private yacht party, though guests often opt for smart casual attire. The key is to wear comfortable, weather-appropriate clothing that allows you to enjoy the sailing experience.
Can I Customize the Itinerary for a Private Sailing Experience?
Yes, you can typically customize the itinerary for a private sailing experience. Many providers offer flexible routes and activities to accommodate your preferences and interests, so you can tailor the outing to your liking.
The Sum Up
For unparalleled sailing adventures on Long Island, choose from a range of options, including private yacht charters, boat rentals, and guided sailing experiences. Explore the scenic Hamptons, Montauk, and Sag Harbor, or set sail on the Great South Bay and Long Island Sound. With a diverse selection, you’re sure to find the perfect sailing excursion to suit your interests and preferences.