Private Long Island Sound Sailing Experience

A Sail Through Long Island Sound: What to Expect from the Private Experience

Imagine cruising along the shimmering waters of Long Island Sound in a private boat with just your group of six or fewer, taking in the sights of millionaire mansions, historic lighthouses, and the distant New York City skyline. For $650, this three-hour private sailing experience offers not just a scenic ride but a chance to actively participate in sailing the boat—furling sails, steering, and feeling the wind in your hair.

What we love about this tour is its blend of relaxation and engagement. First, the personalized nature of a private charter means you can set your own pace and focus on what excites you most. Second, the chance to anchor for lunch and swimming adds a refreshing twist—imagine diving into the cool waters off the boat after a day of sailing.

A possible consideration? The non-refundable policy might catch some off guard, so it’s worth planning your day carefully. This experience is perfect for celebrations like birthdays or anniversaries, as well as for anyone curious about the boating world and seeking a unique perspective of the New York area from the water.

Key Points

• Private & Personalized: Only your group on the boat, with the ability to participate actively.
• Scenic Views & Landmarks: Mansions, lighthouses, and NYC skyline views.
• Flexible & Engaging: Opportunity to sail, anchor, swim, and relax.
• Ideal for Special Occasions: Perfect for birthdays, anniversaries, or bachelorette parties.
• Short but Rich Experience: Three hours provides a well-paced, memorable outing.
• Cost-Effective Group Experience: About $108 per person for a group of six, blending intimacy and value.

Exploring the Long Island Sound by Private Charter

Setting out from Port Washington, NY, this three-hour tour offers a chance to see the stately waterfront mansions of Great Neck’s Kings Point and Sands Point. These homes, often multi-million dollar estates, give a glimpse into the luxurious lifestyles of Long Island’s elite. As you glide through the waters, you’ll also pass by Execution Rocks and Steppingstone Lighthouse, historic sentinels that have guided mariners for generations.

One of the main attractions is the unique perspective this tour provides on the Long Island coastline. Unlike a crowded ferry or a generic boat tour, this private experience allows you to get closer to the waters and customize your journey. You can choose to anchor for a picnic lunch or take a swim, which many travelers find adds a delightful element of spontaneity and fun.

The Itinerary: What You’ll See and Do

The tour begins at Port Washington, where Captain Steve or his crew will greet you and get you comfortable aboard the boat. The first part of your sail takes you into Manhasset Bay, a calm and protected harbor ideal for first-time sailors and those simply wanting a gentle cruise. We loved the way this initial stretch sets a relaxed tone, giving everyone time to settle in.

As you move into the Long Island Sound, the sights unfold—the impressive waterfront estates of Great Neck’s Kings Point and Sands Point are impossible to ignore, their manicured lawns and grand facades visible from the water. The thrill of seeing these homes from the sea adds a touch of Hollywood glamour to your day.

Continuing on, you’ll see Execution Rocks Lighthouse, a striking structure built in 1952, and Steppingstone Lighthouse, both iconic beacons in the harbor. The contrast between these weathered structures and the sleek boats passing by is poetic.

As the boat nears Hart Island and City Island, you get a broader sense of the area’s geography and maritime history. If weather permits, Captain Steve may suggest anchoring at a scenic spot for a lunch break—bring your own picnic or snacks to enjoy on deck. Many guests enjoy a quick swim in the cool waters, a perfect way to refresh before heading back to port.

The final leg of the cruise offers distant views of New York City’s skyline, an awe-inspiring sight that reminds you just how close the Big Apple truly is. The Throgs Neck Bridge also comes into view, adding to the impressive skyline panorama.

Active Participation and Sailing Skills

Unlike many sightseeing tours, this experience encourages hands-on involvement. Whether you’re unfurling the sails, taking the helm, or practicing tacking and jibing, you’ll get a first-hand look at what it takes to operate a sailboat. This element of participation appeals especially to those interested in boating or looking for a more interactive adventure.

Captain Steve, known for his friendly and approachable style, makes sure everyone gets a turn at the wheel. Some reviews mention that “we loved the way we could participate,” and that being able to furl and unfurl sails made the experience more memorable than just sitting back and cruising.

Practical Details and Considerations

The tour runs Monday through Thursday, from 9:00 AM to 7:00 PM, giving flexibility depending on your schedule. The booking process is straightforward, with confirmation received immediately. The activity is private, so only your group will be on board—ideal for celebrating special occasions.

The price of $650 per group, accommodating up to six people, offers good value considering the personalized service, the time spent on the water, and the potential for active participation. For families or small groups, this creates a comfortable and intimate setting.

One thing to keep in mind is the non-refundable policy. If your plans change unexpectedly, refunds are not available, making it wise to confirm your schedule ahead of time.

Overall Impression: Who Will Love This Tour?

This sailing experience is best suited for travelers who enjoy water-based activities and are curious about sailing but don’t necessarily have much experience. It’s equally appealing to those celebrating a special event—say, a birthday or an anniversary—and to anyone wanting a personalized, scenic escape from the usual sightseeing hustle.

If you’re a fan of luxurious waterfront homes or enjoy the idea of blending a scenic cruise with a bit of sailing involvement, this trip will hit the mark. The fact that you can anchor for lunch and swimming makes it very flexible and fun, especially in good weather.

The Sum Up: Is It Worth It?

For $650, this private Long Island Sound sailing tour offers a compact but comprehensive experience that combines stunning scenery, historic landmarks, and active participation. The chance to see New York’s iconic skyline from the water, alongside the mansions of the wealthy and historic lighthouses, makes it a memorable outing. The private nature of the tour ensures personalized attention, and the option to engage in sailing adds a layer of excitement for those interested in the maritime world.

While the non-refundable policy requires some careful planning, the overall experience offers good value for small groups seeking a special day on the water. It’s particularly well-suited for celebrations, couples, or small families wanting a peaceful yet engaging adventure with plenty of photo opportunities and stories to tell.

FAQ

How long is the tour?
The tour lasts approximately three hours, providing enough time to enjoy the sights, participate in sailing, and relax.

Where does the tour start and end?
It begins and ends at Port Washington, NY, making it convenient for travelers staying in the area or nearby.

Can I participate in sailing?
Yes, passengers have the opportunity to participate in sailing the boat, including furling sails and steering, making it a hands-on experience.

Is this a private tour?
Absolutely. It is a private experience for your group only, with no other guests joining.

What sights will I see?
You’ll see Manhasset Bay, Great Neck mansions, Execution Rocks Lighthouse, Steppingstone Lighthouse, Hart Island, City Island, and the NYC skyline in the distance.

Are there options to swim or anchor?
Yes, you can anchor for lunch and swimming, weather permitting, adding a fun and relaxing element to your sail.

Is this suitable for children or non-sailors?
Most travelers can participate, and the active involvement can be enjoyable for children and adults alike, especially those curious about sailing.

What should I bring?
Bring appropriate clothing for the weather, sunscreen, a hat, and perhaps a towel if you plan to swim.

How is the price justified?
The price covers a private, customizable trip with active sailing, scenic sightseeing, and the intimacy of small-group service, making it a worthwhile splurge for a special day.

This private sailing tour on Long Island Sound combines scenic beauty, historical intrigue, and active fun in a way that’s hard to match. Whether celebrating, exploring, or simply relaxing, you’ll leave with great stories and stunning photos.