Classic Harbor Cruises offers some of the best water sightseeing excursions in NYC: holiday and regular cruises, Family-Friendly, July 4th, NYE, Sunday Brunch, Champagne & Wine Tasting, Fall Foliage, Sightseeing, Thanksgiving Dinner, Valentine’s Day, Pride, Architecture and dozens more.

NYC Insider Guide had the privilege of sailing with Classic Harbor on a Sunset Sail aboard the Schooner Adirondack and it was spectacular!!!!!! Please read our review with tips and the most amazing photos of our Sunset Sail Schooner Adirondack.

Sunset Sail Cruise NYC Aboard Schooner Adirondack

We scheduled ourselves for the Sunset Sail on America 2.0, however the boat was switched to the Sunset Sail aboard the Schooner Adirondack. The two hour cruises are identical and the boats are almost the same. Our cruise was on NYC’s most bittersweet day of the year, 9-11, so we got to admire the Tribute of Lights (lit once per year for 24 hours) from the water and fondly remember our loved ones and heroes we lost that day.

Sunset Sail Skyline Cruise NYC

The crew was wonderful and made sure we received our 3 included drinks throughout the cruise. We captured beautiful views of downtown Manhattan, including the World Trade Center, and then sailed past the Statue of Libery and Ellis Island. Lady Liberty glowed and lit up the sky in the evening just as the sun was setting.

Sunset Sail Cruise Statue of Liberty

Book Now: Classic Harbor Cruises

We did not bring a picnic or snacks, but we should have. You can grab things just before you get on the boat at fresh&co, with sandwiches, salads and snacks, or you can grab something at any deli or grocery in the city. Although our night was very warm, as the day had been very hotel, it will usually cool down on the water in the evening, so be sure bring a covering of some kind if you tend to get chilled. There is no tour narration, so make sure to ask the crew what you are looking at, which will be the downtown Manhattan skyline, World Trade Center, New Jersey, Governors Island, Ellis Island and Statue of Liberty.

Classic Harbor Sunset Cruises are open to adults and kids, however, there is only one ticket price. Make sure to book your Sunset Sail aboard the Schooner Adirondack to make the most of your NYC trip. For additional family-friendly options, see our picks for Classic Harbor Family Friendly Cruises.

Classic Harbor Sunset Sail Cruises


Classic Harbor Family Friendly Cruise Picks


Classic Harbor Holiday Cruise Picks

Holiday and Christmas Cruise Specials

NYC Insider Best Sellers every Holiday Season!!!! Classic Harbor cruises has some holiday treats just for YOU!!! Their upscale cruise line offers dozens of NYC Holiday Cruises, like Cocoa & Carols, Holiday Jazz, Holiday Brunch, Holiday Wine Tasting, New Year's and many more, all year round.

These cruises SELL OUT QUICKLY, so make sure to head over to: Classic Harbor Holiday Cruises to book your sail around Manhattan.

Classic Harbor Family Friendly Cruise Options

All Classic Harbor Sightseeing Boat Cruises



More Info Classic Harbor Line Boat Cruises

Our three classic yachts — the Schooner Adirondack and the Schooner America 2.0 (our sailboats), and the Luxury Yacht Manhattan or Manhattan II (our motorized yacht) are reminiscent of the classic boats that cruised the NYC waters in the past two centuries. Classic Harbor Line Boat Cruises is dedicated to helping locals and visitors alike enjoy the unique wonders of New York City and we hope for the privilege of escorting you on a relaxing, inspiring, and breathtaking cruise through the waters we proudly call home.

Classic Harbor Line Boat Cruises

Classic Harbor Line Boat Cruises

  • Address: 62 Chelsea Piers #103, New York, NY 10011 (23rd and West Side Highway on the North end of Chelsea Piers)
  • More Info: Classic Harbor Cruises

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