Private Long Island Sound Sailing Experience

If you’re dreaming of a relaxed yet memorable outing on Long Island Sound, a private sailing experience could be just what you need. This particular tour, offered by Captain Steve’s Sailing Experience, is marketed as a three-hour private charter in Port Washington, perfect for small groups up to six people. While I haven’t personally been on this exact adventure, I’ve gathered enough details to help you decide if it’s worth your time and money.

What stands out immediately is the personalized nature of this tour. Being private means you won’t be sharing the boat with strangers, which is a huge plus if you’re after a more intimate or flexible experience. The opportunity to participate in sailing—like handling the sails or taking the helm—adds an engaging, hands-on element that many might find more rewarding than just sitting back. Plus, the chance to anchor for a swim or a relaxed lunch sounds delightful, especially if you’re looking to combine scenic views with some downtime.

One thing to keep in mind is the price point of $650 for up to six people. That breaks down to around $108 per person if you’re in a full group, which is fair considering the private nature and the experience offered. However, since the tour is non-refundable and can’t be rescheduled, it’s important to be certain about your plans. Also, while the tour promises stunning views of mansions, NYC skyline, and lighthouses, it’s worth noting that the experience involves a fair amount of sailing—so a bit of a breeze or wind could make it more challenging for those sensitive to rougher waters or unstable footing.

This tour suits travelers who enjoy a mix of sightseeing, activity, and a touch of luxury. Whether you’re celebrating a birthday, anniversary, or just want to indulge in a unique, scenic escape, it can be a meaningful way to enjoy Long Island’s coast. If you’re traveling with kids or prefer a more relaxed, less participatory experience, you might want to weigh whether the active sailing element appeals to your group.

Key Points

• Private and intimate setting for groups up to six
• Hands-on sailing experience available, including steering and handling sails
• Opportunity to anchor for swimming and lunch
• Offers scenic views of mansions, bridges, lighthouses, and NYC skyline
• Non-refundable booking requires firm plans
• Tour duration of about 3 hours balances sightseeing with participation

Exploring the Long Island Sound on a Private Sail

When you’re considering a sailing tour on Long Island Sound, the idea of a private experience like this one by Captain Steve’s Sailing is appealing for several reasons. First, the personalized approach means your group gets exclusive access, which makes for a more relaxed, flexible outing. You won’t be crammed in with strangers, and you can tailor your experience—whether that’s taking the wheel, relaxing on deck, or swimming in the water.

The itinerary appears straightforward but packed with interesting sights. You’ll glide past Manhasset Bay, which is charming and quiet, perfect for a leisurely sail. As you leave the bay, you’ll cross into the wider Long Island Sound, where the real magic begins. The captain will point out spectacular waterfront mansions along Great Neck’s Kings Point and Port Washington’s Sands Point, which are famous for their opulence. If you’re into architecture and luxury homes, this part of the journey offers plenty to admire.

The tour also includes views of notable landmarks like the Throgs Neck Bridge, Hart Island, and the lighthouses of Steppingstone and Execution Rocks. These light stations have their own charm: the Execution Rocks Lighthouse especially makes for a striking photo backdrop, perched against the open water. The distant NYC skyline adds a quintessential urban touch to the otherwise peaceful scenery, giving you a sense of the city’s proximity.

The Sailing Experience

What really sets this tour apart is the participatory aspect. During your time on the boat, you’ll have the chance to unfurl and furl the sails and even take the helm if you’re feeling adventurous. According to some reviews, the captain is welcoming and willing to let guests engage with the sailing process, which can make the experience more memorable. If you’re a boat enthusiast or just curious, this hands-on approach is a bonus.

The three-hour duration strikes a good balance—long enough to see multiple sights without feeling rushed. It also leaves time for relaxation, swimming, or a picnic if you choose to anchor in a calm spot. For those who enjoy water activities, a swim in the cool waters of Long Island Sound can be a refreshing break from sightseeing.

What to Expect in Practice

Starting and ending in Port Washington, the tour makes it easy to access via public transportation or by car. The meeting point is conveniently located, and the schedule runs from morning to evening, giving some flexibility. Once aboard, you’ll likely spend some time sailing around, with the captain providing narration about local landmarks and history.

The view of Manhattan from the water is superb, especially if weather permits clear visibility—something that adds to the appeal of this trip. But be mindful that the tour’s success can depend on weather conditions; wind, rain, or choppy waters could impact your experience. This is typical for sailing trips, so packing accordingly and having a flexible mindset is wise.

Value for Money

At $650, the price reflects the private nature of the experience combined with the chance to participate actively. For a small group, this is a fairly reasonable rate, especially considering the personalized service and scenic value. However, it’s non-refundable, so it’s best to book when your plans are firm.

Who Will Love This Tour?

If you’re someone who enjoys being involved in activities and values exclusive experiences, this sailing trip ticks those boxes. It’s ideal for celebrating special occasions like birthdays or anniversaries, thanks to its intimate setting. The views and landmarks make it a great choice for those interested in architecture, cityscapes, and marine scenery.

Travelers looking for a relaxing water-based outing with some adventure will find this to be a good fit, especially if they’re comfortable with handling a boat or willing to try. It’s less suited for those who prefer a laid-back, purely sightseeing cruise—since sailing involves some participation and balance.

The Sum Up

The Private Long Island Sound Sailing Experience offers a unique blend of scenic beauty, interactive sailing, and exclusivity. It’s a chance to see some of Long Island’s most impressive waterfront properties, enjoy striking views of the NYC skyline, and get hands-on with the sailing process. For smaller groups, couples, or friends celebrating a special day, it promises a memorable outing that balances adventure with relaxation.

While the price is on the higher side for a short trip, the private setting, the opportunity to participate actively, and the scenic stops make it worth considering if you’re after a personalized water experience. Just remember that this isn’t a casual, no-strings-attached cruise—being flexible with weather and plans is key to fully enjoying it.

If you’re looking for a way to mark a special occasion, or just want to experience the waters around Long Island in a more meaningful way, this tour definitely deserves a spot on your radar.

FAQ

Is this a private tour?
Yes, only your group will participate, making for an exclusive experience.

Can I participate in sailing the boat?
Absolutely. You’ll have the chance to unfurl and furl sails, take the helm, and practice tacking or jibing under the captain’s guidance.

How long is the tour?
It lasts approximately 3 hours, giving enough time to see multiple sights and enjoy some sailing.

What sights will I see?
You’ll pass waterfront mansions, see the Throgs Neck Bridge, Hart Island, and the lighthouses at Steppingstone and Execution Rocks, plus get distant views of the NYC skyline.

Is there an option to swim or have lunch?
Yes, you can choose to anchor for swimming and a relaxed lunch, which adds a leisurely element to your trip.

What if the weather is bad?
Weather can impact sailing conditions. Since the tour is non-refundable, it’s best to check the forecast and be flexible with your plans.

How do I get to the meeting point?
The tour starts in Port Washington, NY. It’s near public transportation, making it accessible for most travelers.

If you’re a fan of scenic, participatory water outings and want a private, personalized experience on Long Island Sound, this trip could turn out to be a highlight of your visit. Just go in with a relaxed attitude, prepare for some wind, and enjoy the views and the company.