Sailing Cruises

This sunset cruise in NYC allows you to experience a fun and picturesque New York City sunset by sailing aboard our epic sailboat, Schooner America 2.0! During this sailboat sunset cruise, guests are treated to a complimentary drink by our exceptional crew along with stunning NYC skyline views at sunset! Plus the opportunity to watch our team raise sail and sail through NY Harbor! On this sunset sail of NYC, enjoy the vibrant, warm rays of the sun and watch it sink peacefully into the horizon as we sail past the Statue of Liberty. Looking for a fun activity in NYC to do at sunset? This New York City Sunset cruise on the Schooner America 2.0 is perfect for romantic NYC date night ideas, things to do in NYC while entertaining friends from out of town, or just a relaxing experience in NYC to do right now!

Book now to escape the hustle and bustle of the city with your favorite companions aboard this 105-foot, 1800s-style classic sailboat, America 2.0 for a NYC sunset cruise.

If Schooner America 2.0 is not available please check out Schooner Adirondacks Sunset schedule.

Looking for an epic activity in NYC to do at sunset right now? On this sunset boat cruise in NYC aboard Schooner Adirondack, enjoy a stunning New York City sunset from the Hudson River on a classic sailboat. Join us aboard our beautiful 80-foot schooner, the Adirondack, and join your captain and crew in this peaceful, picturesque sailboat sunset cruise away from the concrete and noise of the city. Whether you are looking for the best date idea in NYC or looking for a way to relax after work with colleagues, this outdoor activity in NYC is sure to create lasting memories. We will be shutting off our engines and setting sail for as much of the trip as possible. Book your NYC sunset boat cruise tickets now and join us aboard the Schooner Adirondack and experience the city's beauty and elegance under the setting sun!

If Schooner Adirondack's Sunset Sail is not available, please take a look at Schooner America 2.0 Sunset Sail schedule.

Enjoy a relaxing and comfortable sunset sail aboard the classic Schooner America 2.0. Our chefs have prepared a Taste of the Sea for you, expertly paired with a wine flight, if you choose to add it. Expect a tapas style tasting menu featuring caviar, smoked trout, ahi tuna, seared scallops and delightful accoutrements to dazzle your palate. Whether you’re celebrating a special occasion or enjoying an indulgent night with friends, our Tides & Tapas tasting and wine flight is sure to satisfy the senses as the perfect sea-inspired tasting while sailing at sunset. Capacity is limited to create an intimate and luxurious NY Harbor experience.

Offering the best NYC sail boat experience around, the Schooner America 2.0 provides a top-rated NYC day sail boat ride in New York Harbor. Schooner America 2.0 is the newest, largest, most elegant yacht in the Classic Harbor Line fleet. On this NYC boat tour, enjoy a day sail on this 105-foot schooner that is perfect for a fun NYC family activity, a top NYC day date idea, entertaining friends, or out of town guests. When you leave the dock aboard this sailboat cruise of NYC, you will forget the mayhem and noise of the city of Manhattan, and you’ll feel the relaxing breeze of New York Harbor! Take in all the iconic sites of NYC from the Hudson River, including Ellis Island and the Statue of Liberty. Get the perspective of the famous NYC skyline from the decks of this stunning NYC sail boat. If Schooner America 2.0 is not available for the date you are interested in, please take a look at Schooner Adirondack’s Day Sail Schedule.

Join us for a fun summer evening aboard the decks of our stunning 105-foot schooner, America 2.0 for live jazz in NYC! Sit back and relax with a glass of champagne in hand and glide through NY Harbor with the sun setting behind the Statue of Liberty or see the NYC Skyline lit up at night on this jazz cruise in NYC. Pass by the NYC skyline and see Manhattan’s financial district at the golden hour in NYC or see its twinkling lights! This sail is a top rated activity in NYC for friends, or for a romantic date night in New York. One of the best ways to have an epic experience in NY Harbor is aboard our classic Schooner America 2.0 for a live jazz show in NYC. Watch as our captain and crew raise sail, experience NYC during summer and get the best vantage point of the Statue of Liberty on this top rated live music experience!

This NYC sailboat ride is offered from April through early November: Experience New York like never before on this NYC sail boat tour, which is a two-hour experience aboard the Schooner Adirondack, an 80-foot, wooden pilot schooner. Within five minutes of leaving the dock on this sailboat cruise of NYC, you’ll forget the mayhem and noise of Manhattan street life, and you’ll feel the relaxing breeze of New York Harbor! Sail past the Statue of Liberty, Ellis Island and get the best views of the NYC skyline with One World Trade Center on this NYC sail boat cruise. Looking for a fun family activity in NYC? This sailboat cruise in NYC is the best fun family thing to do in NYC for families with special kids tickets available. Not only is this sail boat tour in NY Harbor good for families, but is a top rated NYC experience for a group of friends or out of town guests.

Join us on this autumn sail out of the busy city to the elegant, foliage-adorned cliffs of the grand Palisades. See the best fall foliage on the Hudson River on our scenic Hudson River fall foliage cruise to the cliffs of the Palisades aboard one of our classic sailboats. Forming a canyon on the Hudson River north of the George Washington Bridge, the Palisades are among the most dramatic geologic features in New York City’s vicinity. Observe this natural wonder from the open deck of Schooner Adirondack for the best view from the Hudson River. This is an epic NYC outdoor adventure up the Hudson River during Autumn so please make sure to dress for the weather! Lots of warm layers, hats, gloves, and even a lap blanket depending on the temperature & the crisp Autumn breeze is encouraged! Book now for a fun sightseeing experience during Autumn in NYC!

Join us for the Macy’s 4th of July cruise in NYC aboard the Schooner Adirondack. Experience great views of the NYC fireworks, the Brooklyn Bridge and the famous Manhattan skyline! Aboard the Schooner Adirondack, join your Captain and crew for a fun experience in NYC to celebrate the 4th of July. On this NYC fireworks cruise, you’ll be surrounded by other boats in a festive holiday atmosphere, as everyone gets into the 4th of July spirit in NY Harbor! Settle in for a fun night in NYC and the best view of the New York fireworks from the water while sitting aboard Schooner Adirondack’s elegant deck. Due to the confines of safety zones set up by the Coast Guard, maneuverability will be minimal and the ability to raise sails may or may not be possible during this event. An open bar of beer, soda, wine, and champagne is included, along with a delicious prix fixe light hors d’ oeuvres menu. Climb aboard the Adirondack and experience the city's most festive summer night!

Embark on a fun 4th of July cruise in NYC aboard the decks of a beautiful classic sailboat! Schooner America 2.0, a 105-foot classic sailboat, is a modernized tribute to the original Schooner America, which in the 1800s, won the international sailboat race that is now known as the America’s Cup. A night aboard Schooner America 2.0 is a top-rated NYC 4th of July experience! Guests on this NYC fireworks cruise are treated to a complimentary open bar, a delicious prix fixe light hors d’ oeuvres menu, and a 3.5-hour experience on the Hudson River amongst the entire New York July 4th flotilla! Be aboard the most stunning and patriotic yacht in the Classic Harbor Line fleet and enjoy the best New York fireworks! Due to the confines of safety zones set up by the Coast Guard, maneuverability will be minimal and the ability to raise sails may or may not be possible during this event.

Start your summer weekend with a top-rated boat ride in NYC! A mimosa sail aboard the stunning Schooner Adirondack is a fun weekend activity in NYC for locals, or add it to your NYC summer bucket list. Gather with friends and family on this NYC boat tour, or consider it for a fun NYC date idea. An afternoon in NY Harbor aboard our original classic boat, Schooner Adirondack, offers a premium sailing experience in NYC. Schooner Adirondack is an 80-foot wooden pilot schooner that’s been sailing in NYC since 1998. Quickly forget the mayhem and noise of Manhattan and join us for a memorable boat cruise in NYC!

Start your weekend with a boat ride in NYC! Our mimosa sail aboard the stunning Schooner America 2.0 is a top rated NYC summer activity! This is the perfect activity to gather with friends and family or as a fun NYC date idea! All are welcome to enjoy an early afternoon sightseeing experience on the Hudson River on this NYC boat tour. Offering a premium NYC sailing experience, the Schooner America 2.0 is the newest, largest and most elegant sailboat in the Classic Harbor Line fleet. Within five minutes of leaving the dock, you'll forget the mayhem and noise of Manhattan street life as you feel the relaxing breeze of New York Harbor. A sail on America 2.0 is guaranteed to be a memorable experience. So, sit back and relax on this two hour boat cruise in NYC.

Celebrate PRIDE in NYC with Classic Harbor Line and join us for an afternoon sail on one of our classic schooners! This is truly the best way to experience PRIDE in NYC: Sail aboard the schooner Adirondack for a sail through NY Harbor. On this PRIDE Sail in NYC, 100% of net ticket sales will be donated to the Hetrick-Martin Institute (HMI). HMI is the nation’s oldest and largest nonprofit organization serving LGBTQIA+ youth. HMI provides its youth members with access to mental health services, social services, basic needs such as toiletries and clothing, as well as remote and in-person programming services focused on education, workforce development and arts & culture. Support this amazing NYC organization this PRIDE month in NYC! Bring your friends, soak up some sunshine, and sail with us on our PRIDE cruises in 2025 through the waters we proudly call home. This is one of the best PRIDE events in NYC!