Private Sail New York with Brooklyn Sail (Reserve the entire boat)

A Friendly Look at the Private Sail New York with Brooklyn Sail

If you’re dreaming of seeing the Big Apple from a different angle, a private sail off Brooklyn might just be the thing. While I haven’t personally taken this exact trip, based on the glowing reviews and thorough info available, it seems like a truly special way to experience NYC’s stunning waterfront. Whether celebrating a special occasion or just wanting a peaceful escape, this sail offers a personalized, intimate way to enjoy the city’s most famous sights.

What really catches the eye is the private setting for up to six guests. It’s a chance to relax without crowds, with the promise of incredible skyline views and several iconic landmarks passing by just a few feet from the water. Plus, you’re free to bring your own snacks and drinks, making it a fairly flexible way to celebrate, unwind, or even propose. And for those who love a good story about a memorable adventure, the reviews highlight how knowledgeable and friendly the crew are, making the experience feel both professional and personal.

Of course, no trip is perfect for everyone. The main consideration here is the cost — $895 for up to six people, which might seem steep for a short trip, but given the private nature and included amenities, many find it worth the splurge. Also, since it’s weather-dependent and non-refundable if canceled, it’s best to plan your sail during a clear forecast to avoid disappointment. This trip seems best suited for those looking for a relaxed, scenic, and personalized experience, especially if you want to avoid crowded boats and enjoy an exclusive, customizable outing.

Key Points

• Private and personalized experience for up to six guests.
• Iconic NYC sights like the Statue of Liberty, Brooklyn Bridge, and Manhattan skyline pass right by.
• Flexible departure times allow you to choose what works best for your schedule.
• Bring your own food and drinks, making it perfect for celebrations or relaxed afternoons.
• Includes bottled water and a friendly crew that makes you feel at home.
• Weather-dependent activity, so check the forecast before booking.

What to Expect on the Private Sailing Trip

This tour is designed as a relaxed, intimate water adventure that gives you a closer look at New York’s waterside landmarks. Starting from Pier 5 in Brooklyn, the boat is reserved entirely for your group—up to six people—so it’s a good option if you want privacy or a special way to celebrate.

The itinerary is straightforward but packed with visual treats. You’ll sail past the Statue of Liberty, an inspiring symbol of freedom and one of the world’s most recognizable monuments. It’s a pretty magical moment to see her from the water, with many reviews mentioning how close and personal the views are, something you can’t quite get from the land.

Next, you’ll motor under the Brooklyn Bridge, a feat that’s almost as impressive as walking it—except this time, you’ll be cruising beneath it, with the city’s skyline serving as a stunning backdrop. The combination of old-world architecture and modern skyscrapers makes for fantastic photos and a unique perspective on the city’s evolution.

Sailing past the One World Trade Center and Ellis Island, you’ll get a chance to appreciate the scale and beauty of these monuments from the water. Many reviews mention how close the boat gets, making the experience feel both personal and awe-inspiring. Plus, when the crew raises the sail at some point, the gentle breeze and the open water create a peaceful, almost meditative atmosphere—an ideal way to unwind after busy city days.

Finally, you’ll sail by Governor’s Island, which offers a more relaxed, park-like view, and you might even get some time to take in the skyline at sunset, depending on your schedule. The entire ride lasts around two and a half hours, providing ample time to soak in the sights without feeling rushed.

The Experience: Setting the Scene

The reviews paint a picture of friendly, knowledgeable captains who strike just the right balance between engaging and giving you space. One reviewer recounted how their captain, Ian, “captured the proposal moment beautifully,” emphasizing how personal and special the crew’s touch can be. Others describe the trip as “magical,” with many noting the breathtaking sunset views and close-up encounters with landmarks.

Many mention how peaceful and relaxing the sailing is, especially compared to typical crowded sightseeing tours. The boat’s comfort, combined with the soothing sounds of water and the sight of the city’s illuminated skyline, makes for a memorable escape. Plus, the option to bring your own snacks and drinks, and the bottled water provided, means you can turn it into your own personalized celebration—be it an anniversary, birthday, or just a well-earned break.

Price and Value: Is It Worth It?

At $895 for a group of up to six, this experience is in the higher price range for a water tour. However, considering the exclusive nature of the booking, the private setting, and the beautiful views, many guests feel it’s a good investment. It’s not just about seeing the sights; it’s about creating a personalized memory, away from crowds and with the freedom to relax and enjoy.

Guests often rave about the service, with several reviewers mentioning how helpful and friendly the crew are. The fact that it’s a private tour means you won’t share the boat with strangers, which is increasingly valuable in today’s travel landscape where exclusivity and comfort matter.

The duration of about two and a half hours strikes a good balance—long enough to enjoy multiple sights without feeling like the trip drags on. Plus, the ability to choose from different departure times adds some flexibility to fit into your plans.

The Itinerary in Detail

Let’s break down what each part of the trip offers:

• Sailing by the Statue of Liberty: This is a highlight for many. You can get close enough to appreciate her grandeur, and the reviews suggest that the vantage point from the water is unbeatable. One traveler noted, “You come so close to everything,” making it a memorable encounter.

• Motor underneath the Brooklyn Bridge: An iconic sight, especially with the skyline framing it. The experience is enhanced by the fact that you’re not just looking from afar but are right beneath the structure, feeling the scale and history of it.

• Passing One World Trade Center and Ellis Island: These landmarks are steeped in history, and seeing them from the water offers a different perspective. Many reviews mention how impressive it is to be so close, adding a sense of intimacy to the experience.

• Sailing by Governor’s Island: Less crowded and more relaxed, it’s a great spot to appreciate the city’s waterfront parks and open spaces. If the timing aligns, sunset views here can be particularly stunning.

• Raising the sail: Whenever this occurs, it’s a special moment—adding some classic sailing charm and a break from motorized cruising. The gentle motion, combined with the city’s lights, makes for fantastic photographs and a tranquil atmosphere.

Practical Details and Tips

• Meeting point: Pier 5, Brooklyn, NY. It’s accessible via public transportation, which is convenient if you’re staying in Manhattan or elsewhere in NYC.

• Duration: About 2 hours 30 minutes, allowing plenty of time to enjoy the sights and relax.

• Booking: Most travelers book around 26 days in advance, so plan ahead to secure your preferred departure time.

• Food and beverages: Bring your own food and drinks, including alcohol if you like. The boat provides bottled water, adding to the comfort.

• Weather considerations: This experience requires good weather. If canceled due to poor conditions, you’ll be offered a different date or a full refund, so it’s worth checking the forecast before planning.

• Accessibility: Service animals are allowed, and the tour is suitable for most travelers, though it’s always good to consider mobility if you are concerned about getting on and off boats.

Is This Tour Right for You?

This private sailing trip is perfect if you’re looking for an exclusive, relaxing way to see NYC’s waterfront landmarks without the crowds. It’s especially suited for couples celebrating something special, small groups wanting a personalized experience, or anyone who prefers a quieter, more scenic outing. If you’re into photography, the close-up views of the skyline and landmarks are fantastic. And if you enjoy a flexible schedule and the option to bring your own drinks, this tour checks those boxes as well.

However, if you’re on a tight budget or need a more structured, family-friendly outing, this might not be the best choice. Since the trip depends on good weather and is non-refundable, it’s best to plan this as a weather-permitting adventure.

Frequently Asked Questions

How many people can fit on the private sail?
Up to six guests, making it a cozy and intimate experience without feeling crowded.

Is food and drink allowed on the boat?
Yes, guests are welcome to bring their own food and drinks. Bottled water is provided by the crew.

What landmarks will I see during the cruise?
You’ll sail past the Statue of Liberty, under Brooklyn Bridge, and by One World Trade Center, Ellis Island, and Governor’s Island.

How long does the tour last?
Approximately 2 hours 30 minutes, giving plenty of time to enjoy the views and relax.

What is the price, and is it worth it?
It costs $895 per group, up to six people. Many find the private, customizable nature and exclusive access make it a worthwhile splurge.

Can I choose my departure time?
Yes, different departure times are available to fit your schedule.

What if the weather is bad?
The tour is weather-dependent. If canceled due to poor weather, you’ll be offered a new date or a full refund.

Is this experience suitable for children or families?
While most travelers can participate and service animals are allowed, the overall vibe suits small groups seeking a peaceful, scenic escape rather than a family-oriented activity.

To sum it up, this private sailing trip from Brooklyn offers a personalized, scenic, and relaxing way to see some of New York’s most iconic landmarks. If you value exclusivity, beautiful views, and the flexibility to bring your own snacks, it’s a memorable option worth considering. Just keep an eye on the weather, book early, and get ready for a peaceful escape on the water that many reviewers describe as “magical” and “amazing.”