Oyster Bay Two Hour Sailing Experience

Oyster Bay Two Hour Sailing Experience: A Relaxed Escape on Long Island’s Gold Coast

Imagine gliding across calm waters, with a gentle breeze and spectacular waterfront estates lining the shoreline. For just $595 per group (up to six people), you can enjoy a two-hour private sail aboard the beautifully maintained 36-foot Jeanneau on Oyster Bay. From the moment we arrived at the marina at 5 Bay Ave, we knew this would be a memorable escape from busy city life — a perfect way to celebrate a special occasion or simply unwind with family and friends.

What we loved most was the personalized experience—your own private boat, your own pace, with a knowledgeable captain (like Captain Jonathan, who makes every trip feel special). The boat is equipped with modern comforts such as a shaded cockpit and Bluetooth stereo, making the journey not only scenic but also comfortable. Plus, the chance to swim or paddleboard with included gear adds a fun, active element.

A potential consideration is the timing — this experience is weather-dependent, so a bit of flexibility is wise. But overall, it’s suited for anyone looking to enjoy a tranquil, scenic outing with great views and a touch of luxury. Whether you’re celebrating a milestone, eager to learn sailing, or just want a peaceful afternoon, this tour fits the bill.

Key Points

• Private and Intimate: Up to 6 guests, perfect for small groups or special celebrations.
• Flexible Adventure: Options to sunbathe, sail, swim, or paddleboard — all included.
• Spectacular Views: Great vantage point for seeing waterfront estates and sunsets.
• Expert Captain: Local knowledge and decades of experience ensure a smooth, enjoyable trip.
• Convenient Location: Easy access from NYC via Long Island Railroad.
• Weather-dependent: Might need to reschedule if weather doesn’t cooperate.

Discover the Charm of Oyster Bay’s Waterways

The Oyster Bay Two Hour Sailing Experience offers a chance to enjoy Long Island’s famed Gold Coast without the hassle of full-day commitments. We found that the experience strikes a perfect balance between relaxation and activity, providing enough time to settle into the boat and truly soak in the scenery.

The journey begins at the Oyster Bay marina, where the crew welcomes you aboard the WINDSWEPT, a sleek and well-maintained Jeanneau. This vessel is designed for comfort and ease, with a fully shaded cockpit that keeps you cool during the warmer months and an integrated swim platform that invites you to cool off or enjoy some paddleboarding — equipment included.

The Route and What to Expect

While this is a private charter, the emphasis is on enjoying the waterways and the stunning vistas. The captain will steer the boat through Oyster Bay Harbor, offering insight into the local landmarks and waterfront estates that have made this area famous. These stately homes and lush gardens provide a picture-perfect backdrop for photos and a reminder of the area’s historical significance.

A highlight for many is the chance to witness a spectacular sunset — plan an evening trip if you want to see the sky turn fiery orange and pink over the water. During the sail, you’re free to choose your activity. Many guests sunbathe on the deck, relax in the spacious cockpit, or even take a turn at the helm if they’re feeling adventurous.

About the Equipment and Extras

The boat is packed with features to enhance your outing. We appreciated the Bluetooth stereo, which made relaxing or chatting easy, and the YETI soft cooler kept our drinks cold throughout the trip. The standup paddleboard and floats provide additional ways to enjoy the water, especially if swimming is on your list.

The crew’s extensive local knowledge enriches the experience. Captain Jonathan, in particular, was noted for going above and beyond to make sure everyone was having a good time, according to reviews. His familiarity with Oyster Bay’s history and waters made the trip informative as well as enjoyable.

Booking and Accessibility

Booking is straightforward, with most trips booked about 8 days in advance. The experience’s flexibility allows for early morning or evening departures, with hours running from 9 AM to 8:30 PM daily. For travelers coming from NYC, the Long Island Railroad from Penn Station is just steps from the marina, making it easy to combine a quick train ride with a relaxing day on the water.

The tour is entirely private — only your group participates — which makes it ideal for celebrating a special occasion or enjoying a quiet family outing without strangers.

Who Will Love This Experience?

This sailing trip is perfect for those craving a relaxing, scenic escape that combines luxury with authenticity. It’s ideal for small groups celebrating a milestone, couples seeking a romantic sunset sail, or families wanting a fun water activity. The opportunity to learn a bit about sailing and enjoy the natural beauty makes it versatile.

If you’re someone who appreciates stunning views and a peaceful atmosphere, this tour will appeal. As one reviewer put it, “This is an incredible experience,” with particular praise for the amazing views of the local area.

Final Thoughts: Is It Worth It?

In our view, the Oyster Bay Two Hour Sailing Experience offers excellent value for a private, personalized outing. The modern boat, expert captain, and scenic setting combine to create a memorable mini-escape from the hustle and bustle. It’s a relaxing way to explore Long Island’s waterfront estates and enjoy some quality time on the water.

While it’s weather-dependent, the flexibility in rescheduling or opting for an evening sail means you can plan around good conditions. Plus, the included gear — paddleboards, floats, and swimming access — adds value that many similar tours lack.

This experience is well-suited for anyone wanting a luxurious yet laid-back water adventure with stunning views and a private atmosphere. It’s a great pick for celebrating, relaxing, or simply discovering a hidden gem of Long Island’s coast.

FAQ

How long is the sailing experience?
The tour lasts approximately two hours, providing enough time to relax, enjoy the scenery, and partake in activities like swimming or paddleboarding.

Can we book this experience for a specific time of day?
Yes, the tours are available from 9 AM to 8:30 PM, and you can choose morning, afternoon, or evening departures to suit your plans.

Is this a group activity or can I book alone?
It’s a private activity, so only your group will participate — perfect if you want a personalized experience.

What’s included in the price?
The price covers the private boat, a licensed captain, use of water equipment (paddleboard, floats), and amenities like a cooler and Bluetooth stereo.

Can we swim during the tour?
Yes, the boat has an integrated swim platform, and use of swimming gear is included. Many guests enjoy cooling off during their trip.

Is it suitable for kids or non-swimmers?
Most travelers can participate, and service animals are allowed. Non-swimmers should always take precautions and inform the crew.

How do I get to the marina from NYC?
The marina is just steps from the Oyster Bay LIRR station, making it easy to reach via train from Penn Station.

What should I wear?
Dress comfortably for the weather — layers are good for cooler evenings. Non-slip shoes are recommended for safety on deck.

What happens if the weather is poor?
Tours are weather-dependent. If canceled due to bad weather, you’ll be offered a different date or a full refund. Cancellations within 24 hours are non-refundable.

Is this experience good for special occasions?
Absolutely. Many reviews mention celebrating birthdays or anniversaries, making it ideal for marking special moments in style.

In all, the Oyster Bay Two Hour Sailing Experience combines scenic beauty, comfort, and personalized service to deliver a memorable outing. Whether you’re seeking a peaceful retreat or a unique way to celebrate, this private sail offers a genuine taste of Long Island’s famed waterfront lifestyle.