Sail Long Island Sound with Captain Steve

Sailing along Long Island’s coast with Captain Steve offers an intimate look at the region’s scenic waters, historic lighthouses, and grand Gold Coast Mansions. This private 3-hour sunset cruise takes you aboard a comfortable 34-foot Beneteau sailboat, providing a personalized and relaxed way to enjoy New York’s Long Island Sound. Whether you’re celebrating a special occasion or simply seeking a peaceful escape, this experience promises a memorable blend of sightseeing and hands-on sailing.

One of the standout features is the opportunity to bring your own refreshments and soak in a stunning sunset, all while aboard a well-equipped vessel with a U.S. Coast Guard-certified captain. That said, the experience demands some logistical planning — notably, parking is on the street, which might require arriving early. This tour appeals most to those who love the water, enjoy scenic vistas, and are curious about sailing but prefer a guided experience.

Key Points

• Personalized Private Tour: Up to 6 guests, ideal for small groups or couples.
• Sunset Views: Perfect timing for a beautiful, relaxing evening on the water.
• Educational Element: Captain Steve can teach you basic sailing skills if you’re interested.
• Flexible Experience: Bring your own food and drinks to enhance your cruise.
• Historic Sights: See Gold Coast Mansions and historic lighthouses from the water.
• Convenient Location: Starts and ends at the Fathoms Hotel & Marina, with nearby parking options.

An Authentic and Relaxed Sailing Adventure

This tour provides a laid-back yet engaging opportunity to explore Long Island’s coast from the water. The 34-foot Beneteau Oceanis yacht, named “Sales Call,” is spacious enough for small groups and designed to maximize comfort. We loved the way the boat is equipped with a bathroom, kitchenette, and a Bimini top for shade — making the trip comfortable even on hot days or if you want to linger longer.

What sets this experience apart is the chance to learn sailing basics from Captain Steve, who is U.S. Coast Guard certified. If you’re curious about how sailing works, you can get hands-on by learning how to adjust sails and even take the helm. For many, this educational element transforms a simple boat ride into an engaging experience that offers a new skill or at least some good stories.

The timing of the tour, usually 3 hours, makes it perfect for an evening activity. Watching the sunset from the water, with the chimneys of the Gold Coast Mansions and lighthouse beacons in view, creates a magical ambiance. As one reviewer noted, “The sunset views are simply stunning, and the captain’s calm guidance made it feel very special.”

The Itinerary: What’s Included and What to Expect

Starting Point at Fathoms Hotel & Marina

The adventure begins at the Fathoms Hotel & Marina, a convenient launching spot in Port Washington. While there’s no parking on-site, travelers should plan to arrive early to find metered parking on Main Street or free parking in the residential neighborhood nearby. It’s worth the extra effort to get settled before your departure, especially if you’re carrying any gear or refreshments.

First Stop: Manhasset Bay

Your captain will give a safety briefing before the boat gently departs into Manhasset Bay. Within five minutes, you’ll start to notice the sights that make this area unique — from historic lighthouse beacons to the elegant waterfront estates. The initial sail is relaxed, allowing you to get comfortable with the boat and enjoy the fresh air.

Main Sightseeing Segment: Gold Coast Mansions and Lighthouses

The highlight is the guided tour of Manhasset Bay, where you’ll cruise past the grand waterfront mansions that earned Long Island the nickname “Gold Coast.” These stately homes, once summer retreats for the wealthy, now serve as iconic landmarks seen from the water. The boat provides an excellent vantage point for photos and appreciating the scale and style of these historic properties.

Meanwhile, your captain will share stories about the area’s past, adding context to the sights you see. Approximately thirty minutes into the tour, there’s an opportunity for guests to sit back, take in the views, or participate in sailing activities if they wish.

Sunset and Relaxation

As the tour draws to a close, the boat positions itself for the sunset. The changing light cast across the bay, illuminating the mansions and glistening on the water, makes for a truly memorable scene. This is the perfect moment for photos or just enjoying the peaceful surroundings.

Return to Fathoms Hotel & Marina

The cruise concludes back at your starting point, where you’ll disembark after a total of around three hours. Many find this length ideal — long enough to relax and see plenty, but not so long that it becomes tiring.

The Practicalities: Pricing, Booking, and What’s Included

At $850 per group, this experience is priced for small groups of up to six people. That makes it a relatively intimate way to spend an evening, and the cost can be split among friends or family, offering good value for a private, guided sailing experience.

What’s included:
– The sunset cruise aboard the Beneteau sailboat
– A U.S. Coast Guard-certified captain who can teach you sailing basics

What’s not included:
– Food and drinks, so bringing your own refreshments is recommended
– Parking costs, since there are no parking facilities on-site

You’ll want to plan ahead for parking, arriving early to secure a spot on Main Street or nearby residential streets. The tour offers the flexibility to bring your own food and beverages, elevating the experience with a picnic or celebratory drink onboard.

The Experience: What Real Guests Say

Reviewers highlight the relaxed yet informative atmosphere Captain Steve creates. One guest shared, “The captain explained everything clearly and made us feel safe while encouraging us to participate in sailing if we wanted.” Others appreciated the beautiful sunset views, noting that “the setting was perfect for a romantic evening or peaceful escape with friends.”

A common theme is the value of personalized service and the chance to learn a new skill — even if just for fun. The boat’s amenities, including a bathroom and kitchenette, add to the comfort, allowing guests to feel at home on the water.

Who Would Enjoy This Tour?

This sailing trip is ideal for small groups seeking a calm, scenic escape. It’s perfect for those interested in learning about sailing or simply relaxing with a drink while watching the sunset. Families with children over 3, couples celebrating, or friends looking for a unique outing will find it appealing.

However, it’s important to note that this experience isn’t suitable for guests with mobility impairments, vertigo, seasickness, or very young children under 3. Weather conditions can also influence availability, as rescheduling might be necessary in case of heavy rain or high winds.

The Sum Up: Is This Experience Worth It?

For anyone craving a peaceful, scenic evening with a touch of adventure, this cruise offers a genuinely enjoyable way to see Long Island from the water. The combination of beautiful views, educational sailing, and a relaxed atmosphere makes it a standout option for small groups or couples wanting a private, memorable outing.

The price reflects the personalized nature and the inclusion of a knowledgeable captain, making it a worthwhile investment if you value quality, authenticity, and a flexible schedule. It’s particularly suited for travelers who appreciate a slow-paced experience, stunning vistas, and the chance to learn a new skill or simply unwind.

If you’re visiting New York and want a different perspective of the region’s coastline, this sail provides an intimate, beautiful, and educational escape from the hustle and bustle.

FAQ

How long does the tour last?
The experience is approximately 3 hours, making it a perfect evening activity without feeling rushed.

Where does the tour start and end?
It begins and ends at Fathoms Hotel & Marina in Port Washington, with the boat docked at the end of the walkway in front of the hotel.

Is parking available on-site?
No, there’s no parking on the marina property. Guests should plan to park on Main Street (metered) or in nearby residential streets.

Can I bring my own food and drinks?
Yes, guests are encouraged to bring their own refreshments to enjoy during the cruise.

Is the boat equipped for comfort?
Absolutely. The boat has a bathroom, kitchen, shade from a Bimini top, and a deck shower for cooling off.

What if the weather is bad?
Charters may be rescheduled due to inclement weather, such as high winds or rain, as these conditions can make sailing unsafe or less enjoyable.

Who is the captain?
Captain Steve, a U.S. Coast Guard-certified professional, who also enjoys sharing sailing tips and stories with guests.

Is this experience suitable for children?
It’s best suited for children aged 3 and above; younger children or those with mobility or motion sickness issues may not find it suitable.

How do I book?
Reservations can be made online, with options to reserve now and pay later, offering flexibility in planning your trip.

This sailing experience with Captain Steve offers a delightful mix of scenic beauty, education, and relaxation — perfect for those looking to experience Long Island’s coast from a different perspective. Whether celebrating, sightseeing, or simply unwinding, this private sunset cruise delivers a memorable day on the water.