Long Island is a fantastic destination for sailing, thanks to its extensive coastline, scenic harbors, and proximity to New York City. Whether you’re after a peaceful sunset cruise, a private day on the water, or a lively adventure with friends, Long Island offers options to suit all tastes. Our favorite is Captain Steve’s Sailing Experience, which combines stunning views with expert guidance and a relaxing atmosphere. Watching the Manhattan skyline fade into the horizon from the deck is a memory worth making. The other two options—an Oyster Bay sunset sail and a longer, private Long Island Sound charter—offer unique ways to explore the water and make your own adventure.
1. Captain Steve’s Sailing Experience on Long Island
At number one on our list is Captain Steve’s Sailing Experience, a two-hour cruise that combines beautiful scenery with professional guidance. This tour is perfect for those who want to take in the sights from the water while learning the basics of sailing. Captain Steve is an experienced sailor who knows the area intimately, sharing stories about the coast and pointing out landmarks like Kings Point, Hart Island, and the NYC skyline. The boat itself is a well-maintained vessel that offers a relaxed, friendly atmosphere.
What makes this experience stand out is the balance between relaxation and education. You’re not just along for a ride; Captain Steve encourages you to participate in steering the boat if you like, making it interactive. The reviews highlight how personable and knowledgeable Captain Steve is, with one guest noting their surprise at how well they navigated under his guidance. The views during sunset are especially memorable, providing a perfect backdrop for a special occasion or just a peaceful escape. Pricing at $475 per group makes it a good value for a private, intimate experience.
Bottom Line: This tour is ideal for those seeking a well-rounded, personalized sailing trip that combines scenic beauty with a touch of hands-on sailing. Great for couples, small families, or friends wanting a memorable experience.
2. Oyster Bay Two Hour Sailing Experience
Second on our list is the Oyster Bay Two Hour Sailing Experience, a cruise that highlights the spectacular sunsets and diverse wildlife of Oyster Bay Harbor. This tour emphasizes the area’s natural beauty and history, offering a peaceful two hours on a meticulously maintained boat. The vessel, WINDSWEPT, features modern amenities like a fully shaded cockpit, Bluetooth stereo, refrigeration, and a YETI soft cooler—perfect for relaxing in comfort while enjoying the sights.
This experience is noted for its easy booking process and the personable captain, Jonathan, who goes out of his way to ensure everyone has a good time. The reviews reflect how this sail is more than just a ride—it’s an enjoyable, scenic escape. It’s especially suitable for sunset lovers and those celebrating special occasions, with the calm waters and stunning views making it a memorable outing.
While it’s a bit pricier at $595 per group, the inclusion of modern comforts and the intimate setting make this a good value for anyone looking to unwind and enjoy nature. It’s especially perfect for small groups wanting a relaxed, scenic sail with plenty of photo opportunities.
Bottom Line: The Oyster Bay experience offers a scenic, comfortable sailing that’s perfect for relaxing with friends or loved ones, especially at sunset.
3. Private Long Island Sound Sailing Experience
Topping the list as the most comprehensive is the Private Long Island Sound Sailing Experience, a three-hour tour that offers a fully customizable adventure. This private charter tours Manhasset Bay and the Long Island Sound, with sights like the Throgs Neck Bridge, Hart Island, and the iconic lighthouses at Steppingstone and Execution Rocks.
What sets this tour apart is the participation opportunity—passengers can help sail the boat—and the option to anchor for lunch and swimming. The boat is equipped for comfort and flexibility, making it suitable for birthdays, anniversaries, or bachelorette parties. Although it currently has no reviews, its detailed itinerary and longer duration provide a more immersive experience for those who want to spend more quality time on the water.
This tour is priced at $650 per group, which reflects its private, customizable nature. It’s ideal for travelers who want a more active, tailored outing and don’t mind spending a bit more for a personalized experience. The longer duration allows for a more relaxed pace and deeper exploration of the scenery.
Bottom Line: For those wanting a private, flexible sailing adventure with options for swimming and a more involved sailing experience, this tour offers excellent value.
$650.00 per group (up to 6)
How to Choose Your Sailing Experience in Long Island
When deciding between these options, think about your budget, how much time you want on the water, and whether you prefer a guided or more participatory experience. If you’re after a short, scenic cruise with expert narration, Captain Steve’s sailing experience is a great pick. For a relaxing sunset sail in Oyster Bay with modern comforts, the Oyster Bay experience fits perfectly. If you want to fully customize your day and enjoy a longer, private outing, the Long Island Sound private tour is ideal.
Booking early can ensure you secure your preferred date, especially during peak season in summer. Consider your fitness level—these tours involve some sailing, so if you’re looking for a more laid-back cruise, opt for the calmer, shorter options.
In summary, Long Island offers a variety of sailing experiences to suit different preferences. Whether you want a quick scenic outing, a sunset cruise with modern amenities, or a full day of sailing with options to participate, there’s something for all. For a relaxing, scenic, and informative experience, Captain Steve’s sailing tour is highly recommended. For a peaceful sunset with stunning views, the Oyster Bay option is perfect. And for a customizable, longer adventure, the private Long Island Sound voyage delivers a memorable day on the water. Don’t wait too long—these tours fill up quickly during the summer months.