Top New York Sailing

Join the ship in New York City on Friday, October 11 at 5 p.m. You dine ashore in NYC for dinner and we may set sail this evening, weather dependent. Take in the beautiful views of the New York City skyline from the water as we depart for our sailing adventure! From New York City, we sail down the New Jersey Coast and continue up the Delaware Bay, where we transit through the C&D Canal and may anchor in the Sassafras and mud flats of the North Chesapeake before continuing on toward Baltimore. We aim to arrive on Tuesday, October 15 by 5 p.m. In Baltimore, you may choose to disembark, or stay aboard for the Great Chesapeake Bay Schooner Race! Please note: On our transit style cruises, we reserve the right to make adjustments to the itinerary and schedule based upon weather and other factors. This New York City to Baltimore cruise mixes the best elements of our more relaxed “windjammer-style” cruises with an offshore element to bring you a vacation cruise that you will never forget.

There is no more iconic skyline than New York City, particularly by night. With this evening sail, take in the city lights from New York Harbor while listening to live jazz by "The Sounds Waves". Relax against the backdrop of the glimmering lights of the city while sipping Champagne, wine, beer, or a soft drink.

The fall foliage along New York’s Hudson River is considered among the most spectacular in the state, and during this half-day sail you can enjoy all the colors of the countryside from the unique vantage point of the water. Board the 80-foot Schooner Adirondack and cruise north to the Palisade Cliffs, sipping hot cocoa, beer, or wine while taking in postcard-perfect vistas.

Enjoy a more romantic cruise with views of New York City landmarks on this sunset sail, on a classic schooner. Bring your favorite person and 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 included champagne or cocktail, and take in the views of sunset light cast across the city.

Enjoy magnificent views of the Statue of Liberty from the water on this 2-hour cruise. Set sail around New York Harbor on a traditional masted sailboat, the America 2.0, and admire views of Lower Manhattan, New Jersey, and Ellis Island from the water. While on-board, enjoy included drink on deck.

Admire New York’s skyline from the water’s edge, and see its major landmarks illuminated after dark, on this sailboat tour of the New York Harbor. Head to Chelsea Piers, and board the Adirondack: an elegant vessel inspired by 1890s pilot schooners. Sail past the Statue of Liberty and Ellis Island, and admire Battery Park, the Brooklyn Bridge, and other highlights.

Experience the magical sunset over New York City from the water on this evening cruise. Set sail along the Hudson River on a traditional 2-masted sailboat, the Schooner Adirondack, and admire views of landmarks such as the One World Trade Center, Battery Park, and the Statue of Liberty from the water. While on-board, enjoy an included drinks on deck.

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 complimentary wine, beer, and Champagne while looking out over iconic sights like the Brooklyn Bridge, Ellis Island, the Statue of Liberty, and Battery Park.

Enjoy a New York City evening on the water during this 2-hour twilight cruise. Take in views of the Statue of Liberty and Manhattan skyline while the sun sets, and order drinks from the on-board bar (own expense). This is a great way to start a night out in the Big Apple.

Get a glimpse of New York City from a different perspective: from a boat 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. Bring some food to eat while sailing around and sip cocktails from the cash bar.

Take in the sights of New York City and its famed skyline from aboard a sail boat. As you sail around the harbor, enjoy four tastings of both NY State Hard Ciders and NY Fall Seasonal Craft Beer led by the beer and booze experts from Urban Oyster.

This classic private tour showcases the Manhattan skyline and the natural beauty of a stunning sunset. Depart from North Cove Marina near the iconic Freedom Tower and set sail on a tour that highlights the Brooklyn Bridge, Statue of Liberty and more. Pack food and drinks to ensure a memorable evening as you take in stunning views of one of the world's most dynamic cities.

See New York City from the waters of the Hudson River on your own private motorboat tour. Enjoy two hours of sightseeing with stops at the Brooklyn Bridge, Freedom Tower (One World Trade Center) and Statue of Liberty. Bring your group of up to six people along with your own food or drink for this exclusive New York boating experience. Your tour departs from a convenient location in lower Manhattan.

Very different from the classic Manhattan 'Circle Line' or 'booze cruise' visiting the State of Liberty. Here you can sail in a real ocean (the Atlantic, in the Sound) and see the Manhattan skyscrapers off in the distance. The sunsets are amazing. And the sea breeze and comfort of the sail takes you far away from the hustle and bustle of Manhattan. Very private activity, you and your group can enjoy the trip and the views while I skipper the boat with one Crew. BYOB is welcome. I have seen many anniversary, birthday and special occasion parties on board the boat. Meetings are subject to weather, which can change in 24 hours. Confirmation subject to availability of licensed Captain.

Sail the Long Island Sound with Captain Steve. Sit back and relax as we tour Manhasset Bay, nestled between Great Neck's Kings Point and Port Washington's Sands Point. Oogle at the multi million dollar Mansions lining the coast until the bay opens up into the Long Island Sound where New York City's skyline comes into view. During our tour you will see the Throgs Neck Bridge, Hart Island (NYC's potters field), the Steppingstone and Execution Rocks Lighthouses. We welcome newbies and accomplished sailors to take the helm, trim the sales, tack and jibe. Want a more relaxing experience, we can drop anchor in a quiet bay for lunch and a swim. Perfect for birthdays, engagements, anniversaries, bachelorette parties and much more! So leave your worries ashore and let's go sailing!

Enjoy some of the most spectacular views of the Manhattan skyline, New York Harbor, and Statue of Liberty when you book this sunset cruise. Make your own way to Pier 36, hop aboard your vessel, and take to the water just as the sun starts to set. During your excursion, you’ll glide past Lady Liberty, Ellis Island, and the Brooklyn and Manhattan Bridges—and will enjoy marvelous views of the skyline as the lights start to come on.

This 2-hour sunset sail will be the highlight of your New York City stay. Take in close-up views of the Statue of Liberty, Ellis Island and the Manhattan skyline.

See some of New York’s top attractions away from the mobs of people on land during this daytime Statue of Liberty sail aboard a historical sailing ship. Cruise around New York Harbor, and enjoy views of the Manhattan skyline, plus landmarks like One World Trade Center, the Empire State Building, the Statue of Liberty, and Ellis Island.

Set sail in the waters of New York City on the only floating designated landmark around on this wine and cheese waterway experience. Float through the New York City Harbor as you sip on top wines and sample local cheese. Cruise alongside the State of Liberty, Ellis Island, Battery Park, Brooklyn Heights and New York City skylines on this relaxing excursion. This tour is the perfect way to unwind on the water and enjoy some of the city's top attractions while sipping wine.

Savor the traditional New York City brunch with a serious twist on this Big Apple champagne sailing cruise. Tuck into a full buffet, complete with coffee, tea and Prosecco. Enjoy homemade muffins, breads and bagels, plus meats, cheese and more. Relax on board as you make your way through the placid waters surrounding the city and take in epic skylines as you enjoy brunch. This cruise is capped at 40 people, which ensures there's plenty of room on deck. Beer, wine, cocktails and soft drinks are available for purchase.

If you're looking for a touch of luxury while sightseeing in the Big Apple, don't miss this private sailing excursion complete with panoramic views of the NYC skyline. As you set sail from Chelsea Piers, you can sit back as the Hudson River breezes guide your ship along Manhattan's West Side. While you cruise, you can enjoy views of Ellis Island, the Statue of Liberty, and Lower Manhattan landmarks including One World Trade.

Secure your ticket in advance for this New York Harbor sightseeing cruise: prebooking will spare you the fuss of ticket-buying in Manhattan. Settle indoors or out on the 3-level Lady Liberty paddleboat and pass under the Brooklyn Bridge for views of the Statue of Liberty, Ellis Island, and Manhattan’s skyline, including One World Trade Center. Choose a departure to suit you and upgrade to add access to Liberty Island’s grounds.

Valentine Dinner cruise for a small group not to be more than 75 couples. You will sail by the Statue of Liberty, Ellis Island and have the beautiful NYC Skyline as your backdrop. Dinner Menu - Champagne toast or Wine Cesar Salad - Penne Rigate with Fresh Tomatoes and Basil - Baked Tilapia served in a White Wine Sauce - Chicken Francaise - Carving Board of Oven Roasted Pork Loin with Traditional Homemade Applesauce - Medley of Seasonal Fresh Vegetables - Oven Roasted Baby New Potatoes - Assorted Dinner Rolls & Sweet Butter - Chefs Selection of Valentines Desserts - Freshly Brewed Coffee & Herbal Tea There will be a DJ and dancing & Cash bar. Limited seat 150

Admire New York City's famous skyline from the water on this afternoon cruise. Choose from two departure times and set sail around New York Harbor on-board a historic sailboat. Enjoy incredible views of Manhattan and spot landmarks such as One World Trade Center, the Empire State Building, the Statue of Liberty, and Ellis Island. While on-board, help raise the sails or even take a turn navigating the ship.