Private Long Island Sound Sailing Experience

Imagine cruising through calm waters, watching the skyline of New York City fade into the distance while on a boat specifically chartered for your group. That’s what the Private Long Island Sound Sailing Experience promises—a three-hour escape that combines sailing, sightseeing, and the chance to actively steer your vessel. Offered by Captain Steve’s Sailing Experience, this tour combines the thrill of sailing with stunning views of some of Long Island’s most exclusive waterfronts.

One feature we really appreciate is the opportunity for passengers to participate in sailing: you’ll get hands-on experience—furling sails, taking the helm, and helping with tacks and jibes. This interactive element makes it a more engaging and memorable outing than a typical sightseeing cruise. However, it’s worth noting that the cost is $650 per group of up to six people, so this is a premium experience, but one that offers privacy, exclusivity, and personalized attention.

A potential consideration is the non-refundable policy—once booked, changing plans isn’t possible, so it’s best suited for those confident about their schedule. This experience is ideal for a variety of special occasions, from birthdays to anniversaries or even bachelor/bachelorette parties, especially if you’re craving a scenic, active, and intimate escape on the water.

Key Points

• Private and customizable three-hour sailing experience for groups up to six.
• Passes iconic landmarks like NYC skyline, Throgs Neck Bridge, and lighthouse views.
• Hands-on sailing opportunity, allowing guests to participate actively.
• Flexible option to anchor for lunch and swimming, perfect for a relaxed day.
• Ideal for celebrations and special occasions that call for privacy and personalized service.
• Cost reflects exclusivity — a premium experience with significant value for those seeking a memorable adventure.

An Overview of the Long Island Sound Sailing Tour

This private sailing trip offers a refreshing way to see the Long Island Sound from a different perspective. Starting from Port Washington, you’ll spend roughly three hours exploring the waters around Manhasset Bay, enjoying both scenic views and a chance to take the wheel.

What makes this tour stand out is its blend of sightseeing and active participation. Unlike many commercial cruises that merely offer a seat, here you’re encouraged to be part of the sailing—furl sails, tack the boat, and even take the helm if you feel confident. This hands-on involvement enriches the experience, making it ideal for those who love a bit of adventure or want to learn more about sailing itself.

The Sights You’ll See

One of the most appealing aspects of this tour is the opportunity to witness some of the most luxurious waterfront mansions on Great Neck’s Kings Point and Sands Point. These properties, often multi-million dollar, highlight the wealth and elegance of the area.

As you exit Manhasset Bay into the broader Long Island Sound, the views of New York City’s skyline become increasingly prominent. The tour includes sightings of notable landmarks like the Throgs Neck Bridge, the Steppingstone Lighthouse, and the Execution Rocks Lighthouse—each offering unique photo opportunities and a sense of maritime history.

The route also passes Hart Island, known for its historical prison and now a public park, and City Island, a quaint fishing community. Distant views of the cityscape provide a stunning contrast to the natural beauty of the Sound.

Itinerary Breakdown: What to Expect

While this is a three-hour tour, the actual experience is quite fluid, allowing for a relaxed yet engaging adventure.

Start Point: The adventure begins in Port Washington, a charming town with easy access to public transportation. You’ll meet your captain, likely Captain Steve himself, who’s well-known for his friendly demeanor and expertise.

Sailing the Bay and Sound: The first part of the tour involves sailing around Manhasset Bay—a calm, sheltered area ideal for both beginners and experienced sailors. Here, you can learn about the basics of sailing or just enjoy the tranquil waters.

Exploring Landmarks: As you move into the broader Long Island Sound, your captain may point out luxurious mansions, the lighthouse at Execution Rocks, and other noteworthy sights. The boat’s route is flexible, depending on conditions and your preferences.

Anchoring and Refreshing: One of the highlights is the chance to anchor for lunch and swimming. If you choose to stop, you’ll be able to relax, enjoy a picnic, or take a refreshing dip in the water. This feature adds a personalized touch, making the experience suitable for a leisurely day on the water.

Participatory Sailing: Throughout the trip, you’ll be encouraged to help with sailing tasks. Whether you’re a seasoned sailor or a complete novice, the crew aims to make everyone feel involved. Expect to unfurl and furl sails, take the helm, and experience the boat’s movement firsthand.

Meeting Details and Practicalities

The tour begins in Port Washington, a town that’s accessible by public transportation, which is a big plus if you’re staying in New York City or nearby. The activity runs Monday through Thursday from 9:00 AM to 7:00 PM, giving you flexible options to fit your schedule.

The booking process confirms your participation immediately, ensuring peace of mind, but it’s important to note that the experience is non-refundable—so plan accordingly.

This private tour is tailored for groups of up to six people, making it perfect for small celebrations or intimate outings. The mobile ticket feature adds convenience, allowing you to show your ticket easily when you arrive.

What Travelers Say and What You Can Expect

While the tour doesn’t currently have reviews, accumulated insights from similar experiences suggest that guests generally appreciate the personalized nature of the trip and the chance to get involved in sailing. Many mention the beautiful views of mansions and city skyline, which provide a luxurious backdrop to your adventure.

Since the tour is private, it’s easy to customize or relax as much or as little as you like. The typical feedback about sailing trips in this area hints at a relaxed yet engaging atmosphere—a good choice if you’re looking to combine sightseeing with some hands-on fun.

Cost and Value Analysis

At $650 for up to six people, this experience averages roughly $108 per person, which is quite reasonable given the exclusivity, personalized service, and the active nature of the tour. When compared to larger commercial cruises, this private option offers more flexibility and a more intimate setting.

The inclusion of sailing participation adds value—you’re not just a spectator but a part of the adventure. Plus, the opportunity to anchor for a swim or picnic enhances the overall experience, making it suitable for a relaxed day on the water.

Who Is This Tour Best For?

This sailing experience is perfect for couples, small groups of friends, or families celebrating special occasions. It offers an intimate setting that’s both fun and educational, especially for those curious about sailing. It’s also ideal for travelers wanting to combine sightseeing with active participation, all while enjoying luxurious views and a peaceful atmosphere.

If you’re seeking a unique, personalized maritime experience with scenic views, this tour provides a wonderful balance of adventure and relaxation. Just keep in mind that the non-refundable policy means it’s best suited for those confident in their plans.

The Sum Up: Why Consider This Experience

The Private Long Island Sound Sailing Experience offers a rare chance to enjoy New York’s waterfront from a different angle—on a private boat that allows for both sightseeing and active involvement. It’s perfect for celebrating a special day, or simply indulging in a scenic escape away from busy city life.

With its flexible, personalized approach, you’ll love the opportunity to learn sailing skills, pass by luxurious mansions, and take in iconic sights like the NYC skyline and lighthouse beacons. The privacy and small group size create an atmosphere that’s both relaxed and engaging, making it ideal for those wanting a more intimate and customized outing.

The cost reflects the exclusivity and experience, making it well worth the price for travelers seeking something memorable and unique. Whether you’re a sailing enthusiast or a first-timer, this trip promises a delightful blend of adventure, luxury, and scenic beauty, perfect for creating lasting memories.

FAQ

What is the duration of this tour?
The tour lasts approximately three hours, giving you plenty of time to enjoy sailing, sightseeing, and relaxing on the water.

Where does the tour start and end?
It begins and ends in Port Washington, NY. The meeting point is easily accessible, and the trip is designed as a round trip with no additional transportation needed.

How many people can join this tour?
Up to six guests can participate, which makes it ideal for small groups, couples, or families looking for a private experience.

Can I participate in sailing?
Yes, passengers are encouraged to help with sailing activities like furling sails and taking the helm. It’s designed to be an interactive, hands-on experience.

Is the experience suitable for children?
Most travelers can participate, so children comfortable with boat environments should enjoy it. It’s best to check with the provider if you have younger kids or specific needs.

What sights will I see?
Expect views of Mansions of Great Neck’s Kings Point and Sands Point, Execution Rocks Lighthouse, Throgs Neck Bridge, Hart Island, and distant NYC skyline.

What should I bring?
Bring weather-appropriate clothing, sunglasses, sunscreen, and perhaps a camera. If you plan to swim, pack a swimsuit and towel.

Is there a lunch break or swimming?
Yes, you can choose to anchor the boat for lunch and swimming, making it a customizable and relaxing experience.

Can I cancel or reschedule?
No, this experience is non-refundable and cannot be changed once booked, so plan accordingly.

This private sailing adventure offers a wonderful way to explore Long Island’s waters in comfort and style—perfect for those seeking an active, scenic, and exclusive outing that leaves lasting memories.