Long Island’s coastline and waterways are a haven for sailors and water enthusiasts. With its mix of posh beaches, historic harbors, and scenic open waters, it offers some of the best sailing opportunities on the East Coast. Whether you’re dreaming of a luxurious private yacht in the Hamptons or a relaxed two-hour sail with stunning city views, Long Island’s sailing options are diverse enough to suit different tastes and budgets. The region’s waterways provide a backdrop for memorable outings, whether you’re celebrating a special occasion, learning to sail, or just seeking a peaceful escape on the water.
What makes Long Island stand out for sailing is its combination of luxurious, guided experiences and tailored private rentals. You can hop aboard a yacht with all the amenities, enjoy a guided sail with local expert Captain Steve, or rent your own boat for a day. Each option provides a unique way to see the coast, with some tours focusing on celebrity homes and scenic coves, while others emphasize hands-on sailing or private customization.
1. Private Yacht Charter in The Hamptons, Montauk or Sag Harbor
At the top of our list is the Private Yacht Charter in The Hamptons, Montauk or Sag Harbor. This tour offers a luxurious, customizable experience aboard a fleet of over 30 boats and yachts ranging from 22 to 100 feet. Starting at around $2,390 per group, it’s an excellent choice for celebrating a special event like a birthday, bachelorette party, or family reunion. The tour typically lasts 2 to 4 hours, giving you plenty of time to explore the picturesque shorelines, hidden coves, and even spot celebrity homes along the coast.
This private charter excels in offering a tailored experience—you can choose to focus on celebrity homes, enjoy water sports with supplied toys like Sea Bobs, or simply relax on deck with drinks and good company. The crew’s expertise makes it easy to customize your route, and the boat options ensure your comfort whether you’re on a sleek yacht or a smaller vessel. Reviews highlight the professionalism and flexibility of the team, with many guests calling it “the finest fleet in the Hamptons.” It’s ideal for anyone wanting a luxury outing with privacy and plenty of onboard amenities.
Bottom line: If you’re looking for a private, high-end experience with options for water activities and celebrity sighting, this yacht charter delivers. Book early as it’s very popular, especially in summer.
2. Captain Steve’s Sailing Experience on Long Island
For those interested in learning to sail or enjoying a guided sailing tour, Captain Steve’s Sailing Experience offers a 2-hour adventure with a personal touch. Priced at $475 per group (up to 6 people), it’s perfect for small groups seeking a relaxed, interactive, and educational outing. Captain Steve’s extensive knowledge of the area, combined with his friendly approach, makes this trip stand out.
The tour emphasizes beautiful scenery from the water, with Captain Steve guiding you to the best spots like Kings Point, City Island, and even NYC skyline views. Guests can participate in sailing the boat, making it more than just a sightseeing cruise—it’s a hands-on experience. Many reviews mention how Captain Steve’s commentary and guidance added value, along with the stunning views of Great Neck Estates and Hart Island. It’s especially suited for those who want to learn the basics of sailing while enjoying a peaceful boat ride.
Bottom line: Perfect for small groups who want a more personal, educational experience with spectacular city and water views, and a guide who shares his sailing expertise.
3. Boat or Yacht Rental in Sag Harbor, The Hamptons, or Montauk
If you prefer complete flexibility and privacy, the Boat or Yacht Rental in Sag Harbor, The Hamptons, or Montauk is a fantastic choice. Starting at $1,990 for about four hours, it’s suitable for groups of up to 8 people. This option puts you in the captain’s seat—either with a crew to assist or fully self-guided—allowing you to craft your own itinerary.
This rental service emphasizes personalized experiences, whether you want a romantic sunset cruise, a fun day exploring coves, or a lively party with friends. Their staff provides expert guidance and insider tips to help you get the most out of your time on the water. Many renters appreciate the flexibility and focus on creating a custom experience, making it ideal for those who want to control their route and activities.
While it might lack some of the packaged amenities of luxury charters, this option shines for its value and customization. It’s best suited for confident sailors or those eager to learn, and who want to avoid the crowds of larger tours.
Bottom line: If you want total control over your sailing day and enjoy hands-on involvement, this private rental offers excellent value and flexibility.
4. Private Long Island Sound Sailing Experience
Rounding out our list is the Private Long Island Sound Sailing Experience. Priced at $650 for up to 6 people, this 3-hour tour gives you a personalized sailing adventure across one of Long Island’s most scenic waters. The tour explores Manhasset Bay, where you can enjoy sightings of multi-million-dollar mansions, and the boat allows you to participate in the sailing process.
What makes this tour stand out is the option to anchor for a swim and lunch, making it perfect for a casual, relaxing day. You can also choose to just sit back and take in the views, with sights including the Steppingstone and Execution Rocks lighthouses, the NYC skyline, and local harbors. It’s ideal for birthdays or anniversaries, offering a private and intimate setting that’s less crowded than larger charter tours.
While it has no reviews yet, the focus on participation and scenic beauty makes it attractive for those looking for a hands-on sailing experience without the luxury price tag. Plus, the smaller size allows for a more personal connection with the crew.
Bottom line: If you want a flexible, participatory sailing experience with stunning views and a chance to swim, this tour is a solid choice.
How to Choose Your Long Island Sailing Experience
When selecting your ideal sailing trip, consider your budget, time available, and what kind of experience you want. If luxury and privacy top your list, the Private Yacht Charter offers unmatched comfort and customization. For a more interactive sailing lesson or guided tour, Captain Steve’s experience provides a personal touch and scenic views. Those seeking total control over their schedule and activities might prefer the boat rental, especially if they have sailing experience. Finally, for a relaxed, scenic day with options for swimming and easy participation, the Long Island Sound sailing offers a well-rounded private adventure.
Booking early is advisable, especially in peak summer months, as these tours tend to fill up fast. Think about whether you want a guided, all-inclusive luxury cruise or a self-directed rental where you can set your own pace.
Final Thoughts
Long Island’s sailing options provide a wide range of experiences suited to different interests and budgets. For a luxury outing with celebrity sightings and water toys, the Private Yacht Charter is hard to beat. Those who want to learn to sail or enjoy a guided water tour with spectacular city views will find Captain Steve’s experience perfect. If independence appeals more, the private boat rental offers customization at a great price, especially for confident sailors. Finally, for a scenic, participatory outing, the Long Island Sound private experience provides a relaxed day with plenty of opportunity to enjoy the water.
Whatever your choice, booking early and clarifying your priorities will help ensure a memorable day on Long Island’s beautiful waters.