Top New York Sailing Tours

Admire New York City from the water without squeezing onto crowded public ferries when you take a private tour in a classic sailboat. Board your vessel at the Chelsea Piers Marina and set sail with an expert crew. Glide past landmarks including the Statue of Liberty and Ellis Island, and admire the Big Apple from a rare peaceful vantage point. An ideal tour for couples seeking a romantic experience.

Experience a magical sunset over New York City from the water on this evening cruise. Sail along the Hudson River on a traditional 2-masted schooner, the Adirondack, and admire views of landmarks such as the One World Trade Center, Battery Park, and the Statue of Liberty. While on-board, enjoy one included drink on deck. You can bring your own snacks too, if you like.

Here are some reasons why people enjoy sailing with Captain Steve. Beautiful Scenery, that is best enjoyed from the water. With Captain Steve's Sailing Experience, you can experience the beauty of the area from a unique perspective. Professional Guidance: Captain Steve is an experienced sailor who knows the area well. He can provide you with professional guidance on how to sail and show you the best places to visit. Relaxation: Sailing is a relaxing activity that can help you unwind and forget about the stresses of daily life. Captain Steve's provides a peaceful and calming environment that allows you to escape from the hustle and bustle of city life. Adventure: Sailing with Captain Steve's Sailing Experience is an adventure. You can experience the thrill of sailing on the open water and explore new places.

By far the best way to admire New York City’s iconic skyline is from the water. With this day cruise along the Hudson River, you can take in the most recognized cityscape in the world while relaxing on board the elegant Adirondack schooner. Sip a complimentary wine, beer, and Champagne while looking out over iconic sights like the Ellis Island, the Statue of Liberty, and Battery Park.

Admire New York City’s iconic skyline from the water—without competing for a view on the ferry—during this private sightseeing cruise. Settle back and relax on a 28-foot (8-meter) luxury powerboat. Rides are limited to only six passengers, so you won’t have to struggle to see. Cruise past the Freedom Tower, Brooklyn Bridge, Statue of Liberty, and more, ticking off dozens of Big Apple attractions in just an hour.

See New York City's landmarks and skyline from the water—and enjoy views many other visitors miss—on this private boat tour. Board your own personal luxury vessel in Lower Manhattan then set sail on New York City Harbor, past the Brooklyn Bridge, One World Trade Center, Statue of Liberty, and more.

Enjoy New York City views that are only reachable from the water—at the most photogenic time of day— during this sunset sailing cruise aboard a classic schooner. Hop aboard the sailboat for your adventure, where you can admire the views of NYC's skyline, and the buildings of Lower Manhattan. Sail onward toward Ellis Island and Lady Liberty, sip a complimentary drink, and take in the views across the city.

Admire New York City's famous skyline from the water's edge—and cruise around the New York Harbor's top attractions—on this unique tour aboard a historic tall sailing ship. Enjoy up-close views of landmarks such as the Brooklyn Bridge, the Statue of Liberty, and Ellis Island along the way. While aboard, you have plenty of time to relax and purchase drinks from the on-board bar.

You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see the East End of Long Island, and sailing aboard our unique schooner makes the experience extra special. Unlike private charters that are widely offered in the area, this ticketed sail allows you to get on the water at a more affordable price.

Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and the impressive estates that line the bay. WINDSWEPT is meticulously maintained and equipped with modern amenities. Features include a fully shaded cockpit with an integrated swim platform, Bluetooth stereo, refrigeration, YETI soft cooler, and folding cockpit table. Private sailing charters are perfect settings for celebrating special occasions, enjoying a relaxing day on the water with family and friends, or hosting memorable client events. Those coming from NYC can take the Long Island Railroad (LIRR) from Penn Station to the Oyster Bay stop, which is steps to the marina!

Step aboard a sailboat for a relaxing evening cruise around New York City. From the outdoor open-air decks, catch views of the skyline, the Statue of Liberty, and Ellis Island lit up at night.

Experience the Manhattan skyline and the natural beauty of a New York City sunset from the water on this private sunset boat charter. With space for 2–6 people, it's ideal for couples, families, and small groups. Depart from North Cove Marina in Manhattan and set sail on a cruise that highlights the Brooklyn Bridge, the Statue of Liberty, and more. Relax during a memorable evening as you admire the views of this dynamic city.

Soak up magnificent views of New York Harbor, including the Statue of Liberty, on this day cruise aboard a traditional masted schooner sailboat. Glide past the One World Trade Center and Manhattan's towering Financial District, Ellis Island, the Brooklyn Bridge, and more, and toast the views with an included drink on deck.

Get a glimpse of New York City from a different perspective: from a classic tall ship sailing around New York Harbor. This tour of the waters around New York features incredible views of the Manhattan skyline and live music from a jazz quintet. Includes two glasses of wine and a cash bar onboard.

The fall foliage along New York’s Hudson River is considered among the most spectacular in the New York City area. Enjoy the colors of the countryside from the unique vantage point of the water during this half-day sail on a classic sailboat Cruise north along the Hudson River to the Palisade Cliffs, sipping a complimentary drink, and taking in postcard-perfect vistas.

Set sail for an unforgettable 2-hour journey on the Peconic River and Orient Harbor, accompanied by live music that enhances the serene atmosphere. With only 20 tickets available, this intimate experience allows you to relax and enjoy original Folk-Pop tunes with a Celtic twist performed by Driving Route 9, hailing from East Haddam, CT. This limited-time event is perfect for music enthusiasts and those looking to enjoy a unique night on the water. Don't miss out on this special opportunity to combine beautiful scenery with captivating melodies.

Make the most of your time in New York City by taking a tour that includes transportation. Take a bus ride past the 9/11 Memorial, Central Park, Rockefeller Center, and more. Then hop aboard the Staten Island Ferry to see the Statue of Liberty and Ellis Island.

Set sail in New York Harbor and enjoy stunning nighttime skyline views on this boat tour aboard a classic schooner. Cruise past iconic landmarks such as the Statue of Liberty while enjoying a peaceful, romantic setting. This 80-foot (24-meter) schooner, designed after 1890s pilot schooners, offers a truly unforgettable nighttime harbor experience.

Set sail on Long Island's Gold Coast with a private 3-hour sailing charter for up to 6 guests aboard WINDSWEPT, a Jeanneau 36i. This charter offers flexible departure times, allowing you to choose a start time that suits your schedule. Private charters are perfect for celebrating special occasions with friends and family, client outings, or learning to sail. Your charter includes a licensed US Coast Guard OUVP Captain with decades of sailing experience. Bottled water and ice are included, and you're welcome to bring your own food and drinks for a relaxing day on the water. Enjoy scenic views of the waterfront mansions that line the bay, help sail the boat, take in a spectacular sunset, or take a refreshing swim - you are free to choose your own adventure! - Private sailing charter for up to 6 guests - Flexible departure times to fit your schedule - Includes bottled water, ice, and onboard refrigeration - Perfect for sunset cruises or leisurely harbor tours - Swimming is permitted

Set sail aboard the Bonnie Lynn for a delightful 2-hour public schooner experience in Greenport. Departing from Stirling Harbor, this sail offers the opportunity to enjoy the scenic beauty of the waters while indulging in a BYOB policy and light picnics (no large coolers). Suitable for guests aged 5 and up, this adventure is perfect for families and friends looking to relax and connect with nature. Limited spots are available, so get your tickets early for this memorable nautical journey!

Give your legs and feet a break—and your ears a treat—during this NYC sightseeing cruise, which includes a live jazz performance. Set sail in the New York Harbor on a 105-foot (32-meter) Schooner, enjoying sweeping sunset views overlooking the Manhattan skyline. Admire attractions like the Empire State Building and Statue of Liberty while listening to jazz rhythms. Plus, a complimentary drink is included per person.

Get out on the water in New York with this private sailing charter for groups of up to six passengers. Set sail from Brooklyn and enjoy views of the Brooklyn Bridge, World Trade Center, Statue of Liberty, Ellis Island, Governor’s Island, and the Manhattan skyline. Guests are welcome to bring their own food and drinks.

Enjoy time out on the water and gain a different perspective on New York with this private boat charter, with space for up to six passengers. Set sail around New York Harbor on a classic sailboat and cruise past Ellis Island, the Statue of Liberty, Governor's Island, the Brooklyn Bridge, and more, while learning more about each landmark and their history.