Oyster Bay Two Hour Sailing Experience

If you’ve ever wanted to see Long Island’s scenic coast from the water, the Oyster Bay Two Hour Sailing Experience offers a well-paced and intimate way to do just that. While we haven’t personally set sail on Windswept, reviews and detailed information paint a compelling picture of what you can expect — from spectacular sunsets to the chance to learn a bit about sailing while relaxing on a comfortable vessel.

What genuinely stands out is the beautiful setting of Oyster Bay Harbor, with its waterfront estates and diverse birdlife. Plus, the fact that the boat, Windswept, is meticulously maintained and equipped with modern amenities makes this experience not only picturesque but also comfortable.

A potential drawback? Because the experience is limited to just two hours, it’s a quick taste of sailing — not a full-day adventure. But for those seeking a relaxing, private outing with stunning views, it hits the sweet spot. This tour suits couples celebrating, families wanting a memorable day, or small groups looking to enjoy Long Island’s scenic coast without the fuss of a large cruise.

Key Points

• Private and Personalized: Only your group of up to six people on a well-equipped sailing yacht.
• Spectacular Views: Perfect for sunsets and scenic waterfront estates.
• Flexible Activities: Sunbathing, sailing, swimming, or relaxing in the cockpit.
• Convenient Access: Easily reachable from NYC via Long Island Rail Road.
• Modern Amenities: Bluetooth stereo, refrigeration, float equipment, and a professional captain.
• Great for Special Occasions: Birthdays, anniversaries, or just a luxurious day on the water.

Setting the Scene: What the Tour Offers

The Oyster Bay Two Hour Sailing Experience is hosted on Windswept, a 36-foot Jeanneau sailboat designed for comfort and style. It’s built for private charters, accommodating up to six guests — making it ideal for small groups or families wanting an exclusive outing.

Starting at 5 Bay Ave, Oyster Bay, the meeting point is straightforward, with easy access from Manhattan—just hop on the LIRR from Penn Station and arrive steps from the marina. Operating year-round between June and November, this experience fits well into a summer or early fall itinerary, when the weather tends to cooperate.

During the cruise, the captain takes you through historic Oyster Bay Harbor, offering views of the famous waterfront estates that line the waterway. These grand homes, some built during the Gilded Age, add a touch of elegance to the scenery. As you cruise, you have the freedom to set the tone — whether that’s soaking up the sun, taking the helm, or cooling off with a swim in the harbor’s safe waters.

The Experience: What to Expect

The two-hour cruise, while short, manages to pack in plenty of memorable moments. Your captain, a U.S. Coast Guard licensed professional with decades of experience, ensures safety and offers insights into local sailing and history. Many reviewers mention Captain Jonathan for his friendly attitude and attention to guest comfort.

Highlights of the journey include:

• Stunning Water Views: Expect picture-perfect vistas of oyster beds, rocky shores, and the lush estates that have made Oyster Bay famous. The ambiance is peaceful, with gentle breezes and the sounds of sailcloth flapping.

• Sunset and Evening Cruises: If you opt for an evening departure, prepare for a breathtaking sunset. The glowing sky reflected on the water makes for a truly special experience, perfect for romantic couples or those wanting a quiet, reflective moment.

• Onboard Comforts: Windswept is well-equipped with modern amenities such as a Bluetooth stereo for music, refrigeration, and a YETI soft cooler for drinks. The fully shaded cockpit offers relief from the sun during warmer days, and the folding cockpit table provides a spot for snacks or drinks.

• Activities at Your Pace: You’re free to sunbathe, relax, take photos, or even get involved in sailing if you wish. Equipment including floats and a stand-up paddleboard is included, offering opportunities to cool off or get a different view of the harbor.

• Swimming: The boat’s integrated swim platform and floats make it easy to hop into the water for a quick dip, a favorite among recent reviewers. It’s a perfect way to refresh during a summer cruise.

What Travelers Say About the Experience

One enthusiastic guest, Massimo_P, summed it up: “This is an incredible experience! Booking was easy, and we had amazing views of the local area. Captain Jonathan went above and beyond to make sure everyone was having a great time.” Authentic praise, highlighting both the ease of booking and the quality of the crew.

Another reviewer appreciated the personalized nature of the tour, noting that the private setting made it feel exclusive and relaxed. This is perfect for celebrating a special moment or simply enjoying the water away from crowds.

Practical Details and Tips

• Booking in advance is recommended — most people book about a week before, which suggests spots fill up quickly during peak season.
• The cost is $595 per group, which is a good value considering it’s a private experience for up to six people. When split among friends or family, it becomes quite affordable for a luxury day.
• The tour runs year-round from 9 a.m. to 8:30 p.m., allowing flexibility to choose a time that suits your plans. For best sunset views, aim for late afternoon or early evening.
• Transportation: From NYC, the easiest way is via the Long Island Railroad to Oyster Bay. Once there, the marina is just steps away, making this a convenient escape from the city.

Who Will Love This Experience?

This sailing cruise is perfect for small groups or couples seeking a peaceful, scenic outing. It’s an ideal choice for celebrating a special occasion like an anniversary or birthday, given its intimate setting. Nature lovers will appreciate the chance to see local wildlife and enjoy the quiet beauty of Oyster Bay Harbor.

Sailors at heart will find value in the opportunity to participate in sailing or simply enjoy the craftsmanship and comfort of Windswept. For those new to sailing, the captain’s experience ensures a safe and informative ride, making it accessible for beginners.

The Sum Up: A Quiet Gem for Scenic Water Experiences

If you’re after a relaxed, private sail through one of Long Island’s most picturesque waters, the Oyster Bay Two Hour Sailing Experience offers a charming blend of comfort, stunning views, and personalized service. The modern vessel and thoughtful amenities make it a hassle-free way to enjoy the water, whether you’re celebrating, seeking a moment of tranquility, or wanting to capture memorable photos of the waterfront estates.

This experience shines brightest for those who value authentic scenery and a peaceful atmosphere, away from crowded tourist spots. The sunset cruises, in particular, promise some of the most breathtaking views Long Island has to offer. It’s a wonderful way to see Oyster Bay from a different perspective, with the gentle sway of the boat and the possibility of a refreshing swim adding to the charm.

For travelers looking for a special, intimate escape on the water, this sailing trip offers authentic, memorable moments — at a fair price for a private charter.

FAQ

How many people can join the sailing experience?
Up to six guests can participate, making it an exclusive and intimate outing.

What is included in the price?
The fee covers the private sailing charter, use of the boat’s amenities like floats and paddleboard, and the services of a U.S. Coast Guard licensed captain.

Can I book this experience for sunset?
Yes, you can plan an evening charter to enjoy the spectacular views of the sunset over Oyster Bay.

How do I get to the meeting point?
The starting point is at 5 Bay Ave, Oyster Bay. From NYC, taking the Long Island Railroad from Penn Station to Oyster Bay makes access straightforward and convenient.

Is this suitable for children or non-swimmers?
Most travelers can participate, and the availability of floats and a swim platform makes it family-friendly, especially if kids are comfortable in the water.

What should I bring?
Bring sunscreen, sunglasses, a hat, and possibly a camera. The boat has refrigeration and coolers for drinks, but packing a light snack or beverage is fine.

Is the experience weather-dependent?
Yes, good weather is required. If canceled due to poor conditions, you’ll be offered a different date or a full refund.

Can I cancel if my plans change?
Yes, cancellations are free if made at least 24 hours in advance. Less notice results in no refund.

What if I want to extend the experience or customize it?
The tour is typically two hours, but special requests or longer bookings might be available directly through Windward Sailing Charters.

Is the tour suitable for celebrations?
Absolutely. Many reviews mention it as an ideal setting for birthdays, anniversaries, or just a special day with friends or family.

This sailing adventure is a chance to see Long Island’s coast from a relaxed, personal perspective, making it an experience worth considering for your next trip to Oyster Bay.