Oyster Bay Two Hour Sailing Experience

Imagine gliding across tranquil waters, surrounded by the beauty of Long Island’s famed Gold Coast, with the sun dipping toward the horizon. That’s exactly what the Oyster Bay Two Hour Sailing Experience offers — a chance to escape the hustle of city life and enjoy a relaxed, authentic sailing adventure. Whether you’re celebrating a special occasion, eager to learn about sailing, or simply craving a peaceful afternoon on the water, this private charter promises a personalized, picturesque outing.

Two things stand out about this trip: the stunning shoreline views of historic estates and the modern comforts on board that keep things comfortable and fun. The boat, a well-maintained Jeanneau called WINDSWEPT, is equipped with features like Bluetooth stereo, refrigeration, and a shaded cockpit, making your time on the water both scenic and enjoyable.

One thing to consider is that, at around $595 for up to six people, it’s an investment, but for the quality of experience and personalized attention, many find it well worth the cost. This experience is ideal for small groups looking for a memorable, relaxed outing with a touch of luxury. If you enjoy nature, history, or just a good sunset sail, this trip could be just what you’re after.

Key Points

• Private and personalized: Perfect for up to 6 guests, giving you space and attention.
• Spectacular views: Enjoy sights of historic estates, wildlife, and sunsets.
• Modern amenities: Fully equipped with shade, Bluetooth stereo, refrigeration, and a swim platform.
• Flexible experience: Sunbathe, sail, swim, or take photos — your choice.
• Easy access: Located in Oyster Bay with options for LIRR travelers from NYC.
• Experienced captain: U.S. Coast Guard licensed with local knowledge, ensuring safety and insight.

What the Experience Includes

The heart of this tour is a two-hour private sailing aboard the 36-foot Jeanneau, WINDSWEPT, a vessel that balances elegance and functionality. As you set off from 5 Bay Ave in Oyster Bay, you’ll cruise along the bay’s calm waters, passing by grand estates that whisper stories of Long Island’s Gold Coast era. This stretch of shoreline is lined with impressive mansions, many of which you can see from the water — a real highlight for architecture buffs or anyone interested in local lore.

The captain, with decades of sailing experience, is not only there to steer but also to share insights about the area and harbor. We loved the way the captain’s local knowledge added depth to the experience, making it more than just a boat ride but an engaging glimpse into Oyster Bay’s maritime charm.

The Scenic Tour of Oyster Bay Harbor

Your route covers the historic harbor, where you’ll see the waterfront estates that have long defined the area’s reputation as Long Island’s “Gold Coast.” The views of these mansions, often with lush greenery and manicured lawns right down to the water’s edge, are especially eye-catching at sunset, making evening sails a popular choice.

Onboard Comforts and Activities

WINDSWEPT is equipped for comfort and fun. The fully shaded cockpit offers a cozy spot for relaxing or taking photos, while the integrated swim platform and floats invite you to cool off with a swim or use the standup paddleboard — all included. The onboard Bluetooth stereo adds to the relaxed vibe, whether you’re listening to tunes or just soaking in the peaceful surroundings.

Sunbathers and watersports enthusiasts will appreciate the equipment provided, making it easy to enjoy the water without lugging gear along. The boat’s size and amenities mean you can sit back and enjoy the view, participate in sailing if you’re inclined, or simply unwind with a drink from the YETI soft cooler.

Sunset and Evening Sails

If timing allows, we recommend booking an evening sunset cruise. The way the light hits the water and the estates, casting warm hues across the landscape, turns the experience into a visual feast. The reviews highlight how memorable these sunsets are — “incredible views of the local area” and an experience “we can’t recommend enough,” as one happy guest put it.

Practical Details and Logistics

Getting to Oyster Bay is straightforward, especially if you’re coming from NYC. The LIRR train from Penn Station drops you just steps from the marina, making this a convenient option without needing to rent a car. The tour itself lasts around two hours, which is long enough to relax and see plenty without feeling rushed.

Pricing is $595 per group, accommodating up to 6 guests. While that might seem steep for some, the value lies in the private, customizable nature of the trip, the inclusion of all equipment, and the expertise of the crew. For small groups or families, it’s a more intimate, worthwhile experience than larger boat tours.

Booking is typically done 8 days in advance on average, and the activity runs from June through November — perfect timing for warm weather and clear skies. Cancellation is free up to 24 hours before, which adds peace of mind when planning.

Why Travelers Love This Experience

Feedback from previous guests emphasizes the stunning views and the captain’s personable approach. One reviewer exclaimed, “This is an incredible experience,” and praised Captain Jonathan for going “above and beyond” to ensure everyone had a good time. The private nature of the charter means you can tailor the experience — whether you want to soak up the scenery, learn to sail, or simply relax.

Who Should Consider This Tour?

This sailing adventure is especially well-suited for couples celebrating a special occasion, small groups of friends, or families seeking a low-key day on the water. It’s also a good choice for those interested in photography or history, given the scenic estates and picturesque harbor. The experience’s flexibility and comfort level make it accessible to most travelers, including those with limited sailing experience.

The Sum Up: Why It’s Worth the Cost

The Oyster Bay Two Hour Sailing Experience offers a rare chance to enjoy Long Island’s scenic waterfront in a private, relaxed setting. The combination of stunning vistas, modern boat amenities, and an experienced captain makes this a memorable outing for anyone seeking a peaceful retreat. You’ll love the chance to see the historic estates from the water, relax in comfort, and perhaps even catch a sunset that turns the sky into an artist’s palette.

While the price might seem high compared to larger group tours, the intimacy and personalized attention are what set this experience apart. It’s best for small groups or couples who appreciate a touch of luxury and genuine local insight. If you’re after a peaceful, scenic escape with plenty of photo opportunities and the chance to unwind, this sailing trip hits all the right notes.

FAQ

How many people can join this sailing trip?
Up to 6 guests can participate, making it ideal for small groups or family outings.

What’s included in the price?
The cost covers the private two-hour charter, use of all onboard equipment like floats and paddleboards, and a knowledgeable, U.S. Coast Guard licensed captain.

Is the experience suitable for beginners?
Yes, most travelers can participate, and the captain is experienced in providing a relaxed, enjoyable outing regardless of sailing experience.

Can I choose the time of day?
Yes, you can plan for a morning, afternoon, or evening trip — sunset sails are especially popular for their spectacular views.

How do I get to the meeting point?
From NYC, take the Long Island Railroad (LIRR) from Penn Station to Oyster Bay, which is just steps from the marina.

What should I bring?
Bring sunscreen, a hat, sunglasses, and a camera. Towels and swimwear are recommended if you plan to swim.

What happens in case of bad weather?
The trip is weather-dependent. If canceled due to inclement weather, you’ll be offered a different date or a full refund.

Is there a minimum or maximum booking time?
The experience is fixed at two hours and must be booked in advance with at least 24 hours’ notice for cancellation.

Can service animals participate?
Yes, service animals are allowed onboard.

What’s the best time of year to book?
The tour runs from June to November, with the best weather often in late summer and early fall.

Whether you’re seeking a peaceful day on the water or a scenic celebration, this sailing adventure offers a genuine taste of Oyster Bay’s charm. With impressive views, modern comforts, and a relaxed vibe, it’s a worthwhile splurge for those who value quality and authenticity.