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

Imagine gliding silently past the Statue of Liberty, the Brooklyn Bridge, and the Manhattan skyline—all from the comfort of a private sailboat. That’s exactly what Brooklyn Sail offers with their private sailing experience in New York Harbor. This isn’t your typical sightseeing tour; it’s a chance to see the city’s most famous sights from the water, in a relaxed, personalized setting.

What we love about this experience is how intimate and flexible it is. With a group of up to six, you get personalized attention from knowledgeable guides, and a chance to set your own schedule from various departure times. Plus, the views are simply breathtaking—sunset sailings or daytime cruises both offer unique photogenic moments. One thing to keep in mind: it’s a 2.5-hour experience, so you’ll want to plan around that, and weather can impact whether you sail or not.

This experience is best suited for couples, small families, or friends celebrating special occasions—birthday, proposal, or just a day to indulge in New York’s maritime scenery. If you enjoy being on the water and want a more private, relaxed way to see New York’s iconic sights, this tour ticks all those boxes.

Key Points

• Private boat for up to six guests, ensuring a personalized experience.
• Views of major landmarks: Statue of Liberty, Brooklyn Bridge, One World Trade Center, Ellis Island, Governor’s Island, and Manhattan skyline.
• Flexible departure times and a duration of around 2.5 hours.
• Bring your own food and drinks, with bottled water provided.
• Expert guidance from friendly, knowledgeable captains.
• Perfect for special occasions or just a memorable day on the water.

An Overview of the Experience

This private sailing tour from Brooklyn is a prime way to get away from crowded tourist spots and enjoy New York from a different perspective. For $895 per group, you’re reserving the entire boat, which means it’s an exclusive experience that can be tailored to your interests. The boat comfortably accommodates up to six people, making it ideal for intimate celebrations or small groups wanting a special outing.

The start point, Pier 5 at 8 Joralemon Street in Brooklyn, is easily accessible by public transportation, which adds to its practicality. Once onboard, you’ll have a chance to enjoy stunning views of the city’s most recognizable landmarks. The captain will navigate past the Statue of Liberty, under the Brooklyn Bridge, and along the Manhattan skyline, offering memorable photo opportunities at every turn.

Detailed Itinerary and Landmarks

Statue of Liberty

The tour begins with a sail-by past the Statue of Liberty, one of New York’s most iconic symbols. Seeing her from the water offers a different perspective—larger than life, yet still quite majestic when viewed from the harbor. Several reviewers mention how close they get to her, which makes for impressive photos and a more personal feeling of connection.

Brooklyn Bridge

Next, the boat motors under the Brooklyn Bridge, a feat for any boat lover. Watching this gothic suspension bridge from below, with the Manhattan skyline as a backdrop, is a highlight. As one reviewer put it, “We motor under the Brooklyn Bridge,” which is a unique experience that many sightseeing boat tours don’t offer.

One World Trade Center & Ellis Island

Passing the One World Trade Center gives you a view of the new World Trade complex, symbolizing resilience and renewal. The boat also sails past Ellis Island, where you’ll get a sense of the immigrant stories that built New York. The proximity to these landmarks makes this cruise educational as well as scenic.

Governor’s Island

The boat raises its sail and glides past Governor’s Island, a lesser-known gem with parks, historic buildings, and art installations. Many guests enjoy this quiet slice of the harbor, away from the hustle of Manhattan.

The Sailing Experience: What to Expect

The highlight of this trip is the sailing itself. Depending on the wind and weather, your captain may raise the sail for a true sailing experience or keep the engine running—many reviews mention the pleasure of both motor and sail. One reviewer described it as “such a peaceful sailing,” which underscores how relaxing this can be compared to the hustle of city streets.

Guests are welcomed to bring their own food and drinks, making it perfect for celebrating an occasion or just enjoying picnic-style snacks while soaking in the views. Bottled water is provided, so you won’t go thirsty. The tour typically lasts about two and a half hours, which feels just right—long enough to see everything without it dragging on.

The guides and captains

From multiple reviews, it’s clear the captains are friendly, professional, and knowledgeable. They’re adept at pointing out landmarks and sharing tidbits about the city’s maritime history, adding layers of interest. One reviewer noted that their captain “captured the moment beautifully,” which hints at the personalized touch you’ll receive.

Practical Details and Considerations

Price and Value

At $895 for the whole boat, the cost breaks down to roughly $150 per person—quite reasonable considering it’s a private experience with a dedicated captain. For a special occasion or a group of friends, it offers a memorable alternative to crowded boat tours or expensive helicopter rides, especially given its intimate nature.

Booking and Availability

Most travelers book about 26 days in advance, which is good to know if you’re planning ahead. The tour offers multiple departure times, so you can choose a sunset sail or a daytime cruise—both of which offer distinct experiences. Sunset cruises tend to be especially popular, as the city lights start to glow and the sky turns vibrant.

Weather and Cancellation

As with all outdoor activities, good weather is essential. The tour provides a full refund if canceled due to poor weather, so it’s worth checking the forecast. You can cancel free up to 24 hours beforehand, giving flexibility if your plans change.

Accessibility and Logistics

The tour is near public transportation, making it accessible for most travelers. Service animals are allowed, and most people can participate. It’s a private tour, so only your group will be onboard, ensuring a relaxed and private atmosphere.

Authentic Experiences: What Travelers Say

The reviews paint a picture of consistently positive experiences. Here’s what travelers appreciated most:
– Knowledgeable guides and captains who make the trip both fun and informative.
– The stunning and close-up views of NYC’s most famous landmarks.
– The peaceful sailing, especially during sunset, which many describe as “magical” and “beautiful.”
– The ability to bring your own food and drinks, turning the cruise into a personalized celebration.

One reviewer shared, “I 200% recommend this. I made lifetime memories with my family,” capturing the essence of how special this experience can be.

The Sum Up: Is This Tour Worth It?

For travelers seeking a private, personalized, scenic escape from the crowded streets of Manhattan, this sailing trip offers a distinctive way to experience New York. It’s particularly well-suited for couples, small groups, or families celebrating something special—perhaps a proposal, birthday, or simply a desire for a quiet moment on the water.

The combination of expert guides, intimate atmosphere, and breathtaking views makes this a standout choice. It balances cost and value well—especially given the exclusivity of reserving the entire boat—and offers an authentic perspective on the city’s maritime charm.

Keep in mind, weather can impact your plans, but the flexible cancellation policy and the option to choose different departure times give you peace of mind. The experience’s relaxed pace and stunning scenery make it a memorable highlight for anyone wanting a different view of New York.

FAQ

Is this tour suitable for children?
Most travelers can participate, and since it’s a private experience, you can decide if it’s appropriate for your family.

Can I bring food and drinks onboard?
Yes, you’re welcome to bring your own food and beverages. Bottled water is provided.

How long is the sailing trip?
The trip lasts approximately 2 hours and 30 minutes, making it a comfortable yet substantial experience.

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

Is the tour weather-dependent?
Yes, it requires good weather. If canceled due to weather, you can choose a different date or get a full refund.

How do I book?
Most travelers book about 26 days in advance through the tour provider’s website or Viator. Multiple departure times are available.

What is included in the price?
The price includes the private boat for your group, bottled water, and the guidance of an experienced captain.

Can I participate if I have mobility issues?
Most travelers can participate, but it’s best to check with Brooklyn Sail directly for specific accessibility concerns.

What if I want to celebrate a special occasion?
This tour is perfect for birthdays, proposals, or just a relaxing day. Bring your own food and drinks to tailor the experience.

What is the cancellation policy?
You can cancel free of charge up to 24 hours before the scheduled trip for a full refund.

This private sailing experience from Brooklyn combines the thrill of being on the water with the intimate charm of a customized tour. Whether celebrating or simply seeking a fresh perspective on NYC, it offers a unique, memorable way to see the city from a different angle—quiet, scenic, and personal.