Oyster Bay Two Hour Sailing Experience

Oyster Bay Two Hour Sailing Experience Review

Imagine escaping the hustle of city life for a couple of hours on a sailboat, surrounded by the shimmering waters and historic estates of Oyster Bay. That’s exactly what the Oyster Bay Two Hour Sailing Experience offers—an intimate, flexible cruise that blends scenic beauty with the thrill of being on the water. Whether you’re celebrating a special occasion or simply craving a peaceful day on Long Island’s iconic coast, this outing promises a memorable escape.

What really draws us in are its personalized vibe, the spectacular sunset views, and the opportunity to actively participate in sailing or just unwind with a drink in hand. The boat, Windswept, is a well-maintained 36-foot Jeanneau equipped with modern amenities, ensuring comfort throughout your journey. On the flip side, the cost—$595 for up to six guests—might seem high for just two hours, but considering the private setting, professional captain, and all included equipment, it’s a solid value for an exclusive experience. If you’re seeking a relaxed yet scenic adventure with loved ones or clients, this tour ticks many boxes.

Good To Know

• Private and Intimate: Perfect for groups up to six, offering a personalized experience.
• Flexible Activities: Sunbathe, sail, swim, or just enjoy the views—your day on the water, your rules.
• Modern Comforts: Fully shaded cockpit, Bluetooth stereo, refrigeration, paddleboard, and floats.
• Spectacular Scenery: Views of historic estates, Oyster Bay Harbor, and stunning sunsets.
• Accessible Location: Easily reachable from NYC via LIRR or local transport.
• Weather Dependent: Canceled in poor weather with options for rescheduling or full refund.

Why the Oyster Bay Sailing Experience Stands Out

A Scenic Escape on Long Island’s Gold Coast

Long Island’s Gold Coast is famous for its scenic waterfront, grand estates, and impressive shoreline. The Oyster Bay harbor showcases all of that in a concentrated burst of natural beauty. As we read in a recent review, guests loved the “amazing views of the local area,” emphasizing how the experience really captures the essence of this iconic stretch of coast.

You’ll board Windward Sailing Charters’ Windswept, a well-kept 36ft Jeanneau that feels both sturdy and homey. The boat’s fully shaded cockpit offers comfort, even on warmer days. There’s also an integrated swim platform, perfect for cooling off or taking a quick dip, which is a feature not always available on smaller boats. For those who like to stay connected, Bluetooth stereo keeps your favorite tunes playing during the trip.

The Itinerary and What to Expect

This is a private charter, meaning all six seats are exclusively yours—whether you’re celebrating an anniversary, hosting clients, or just seeking some peace. The departure point is 5 Bay Ave in Oyster Bay, a short walk from the LIRR station, making it a convenient day-trip option from NYC or other parts of Long Island.

Once on board, the captain—experienced and knowledgeable—is there to guide you through the harbor or let you take the helm if you wish. The route typically includes touring the historic Oyster Bay harbor, where you’ll see grand waterfront estates that speak to the area’s opulent past. One of the most praised aspects of this trip is the opportunity to choose your own adventure—whether lounging on deck, taking part in sailing, or jumping into the water if you fancy a swim.

The Sunset Sails and Evening Views

If timing allows, opting for an evening departure is highly recommended. Many reviews mention the spectacular sunset views and the golden light reflecting off the stately mansions—truly a visual treat. The calm water and the gentle breeze make for a romantic, peaceful experience that you won’t forget.

Equipment and Comfort Options

Windswept is equipped with plenty of gear to enhance your day. Besides the boat’s comfortable setup, you’ll find several floats and a standup paddleboard, both included in your booking. These little touches turn a simple cruise into an active adventure or relaxing float session. Guests have noted how convenient it is that everything is included, letting you focus on enjoying the scenery without extra fuss.

The Captain and Crew

The experience is led by a U.S. Coast Guard licensed captain with decades of sailing experience and local knowledge. One reviewer specifically mentioned Captain Jonathan, who “went above and beyond to make sure everyone was having a great time,” which speaks to the personal attention and professionalism you can expect.

Pricing and Value

At $595 for up to six guests, the price averages out to about $100 per person—quite reasonable considering the exclusivity, private setting, and included amenities. For a tailored, scenic outing with friends or family, this fee offers good value, especially when compared to the cost of other private outings or organized tours that include less personalized service.

Booking and Practicalities

Booking is straightforward, usually done 8 days in advance, which is enough time for most travelers to plan. The tour operates from 9:00 AM to 8:30 PM, giving flexibility for morning or evening cruises. Cancellation is free up to 24 hours before, a helpful feature if weather turns sour or plans change unexpectedly.

Who Will Love This?

This experience is best suited for small groups who want a private, scenic, and flexible outing. It’s ideal for celebrating milestones, relaxing with loved ones, or hosting clients in a unique setting. Those looking for a more adventurous, guided sailing trip might want to seek more extensive options, but for peaceful leisure, this cruise hits the mark.

Final Thoughts: Is It Worth It?

In essence, the Oyster Bay Two Hour Sailing Experience offers a tasteful blend of natural beauty, privacy, and comfort that appeals to many travelers. The high ratings and enthusiastic reviews underscore its appeal. Whether you’re captivated by the chance to see historic estates from the water, eager to enjoy a sunset sail, or simply want a quiet getaway, this tour delivers.

The boat’s modern amenities and flexible itinerary make for an enjoyable escape, especially if you appreciate personalized service and stunning views. The cost might be a consideration for budget travelers, but the exclusivity and quality of the experience justify it for those seeking a memorable day on Long Island’s coast.

Who Should Consider This Tour?

This sail is perfect for small groups, couples, families, and corporate parties wanting a private outing without the crowds. It’s suitable for those new to sailing and seasoned sailors alike, thanks to the captain’s guidance. If you love scenic water views, historic surroundings, or simply want a peaceful retreat without sacrificing comfort, this experience ticks many boxes.

For anyone seeking a relaxed, scenic, and customizable sailing trip with a focus on comfort and stunning scenery, this tour offers excellent value and genuine quality.

FAQ

Can I bring my own drinks or snacks?
While the tour includes refrigeration and a YETI soft cooler, it’s best to check with the provider beforehand about bringing your own food or beverages.

Is this experience suitable for children?
Most travelers can participate, and children are welcome. The boat is private for your group, so you can decide how active or relaxed you want the trip to be.

What should I wear?
Dress comfortably and consider layers, especially if you’re taking an evening cruise. Bring sun protection like hats and sunscreen for daytime trips.

How do I get to the meeting point?
The meeting point is near public transportation, specifically the Oyster Bay LIRR stop, making it easy to reach from NYC or other areas.

What happens if the weather is bad?
The trip relies on good weather; if canceled due to poor conditions, you’ll be offered an alternative date or a full refund.

Is the boat accessible for those with service animals?
Yes, service animals are allowed, so you can bring them along for the trip.

In all, the Oyster Bay Two Hour Sailing Experience stands out as a charming, scenic way to explore Long Island’s coastline with a private touch. Whether you’re celebrating, relaxing, or sightseeing, it’s a setting that promises stunning views and personalized service—an outing that many will cherish long after the sails are furled.