Romantic Sails/Cruises

New Year’s Eve Champagne Tasting Cruise

Celebrate this New Year’s Eve with your special someone or your close and dear friends on Classic Harbor Line’s New Year’s Eve Champagne Tasting Cruise! As you cruise on the Yacht Manhattan II, you will be able to take in all the beauty the New York City skyline has to offer while cozying up and staying warm in our climate controlled observatory. This cruise has limited capacity to create an intimate, comfortable and quiet NY Harbor cruise.This special tour features the twinkling lights of Manhattan and a selection of special sparkling wines featuring a delicious flight hand selected by our own wine and food expert.

New York City Lights Holiday Cocoa Cruise

Step aboard the cozy yachts Manhattan or Manhattan II decked out in Holiday decor!  Get into the holiday spirit during this magical time of year and cruise with us in the grand salons of these yachts filled with rich, heart warming full Holiday decor. 

Sunset & Holiday Cocoa Cruise

Experience a beautiful New York City sunset and the illuminated cityscape during a comfortable and unique NYC Harbor sunset cruise through the Hudson and East Rivers. Get into the holiday spirit and enjoy the grand salon of the Manhattan Yachts in their rich full Holiday decor while taking in NYC skyline during this magical time of year.

Live Jazz City Lights or Sunset Sail

Join us for a magical evening of live jazz aboard the decks of our stunning 105 foot schooner.  Sit back and relax with a glass of Champagne in hand and glide through the darkness of NY Harbor with the twinkling skyline as your backdrop or the magical sun setting behind the Statue of Liberty.  This sail is perfect for date night or a group of friends looking to do something unique. Enjoy a live Jazz trio from the decks of this elegant schooner.  (This sail is offered during the city lights time slot as well as the sunset time slot) 

Valentine’s Day Champagne Tasting Cruise

Join us in NYC for a Champagne Valentine’s Day Cruise aboard the luxury yacht Manhattan II.  As you cruise on the Yacht Manhattan II, you will be able to take in all the beauty the New York City skyline has to offer while cozying up and staying warm in our climate controlled observatory. This cruise has limited capacity to create an intimate, comfortable and quiet NY Harbor cruise.  This Valentine’s Day Cruise is one of the best date ideas in the city of Manhattan.  This romantic, intimate and breathtaking NYC Cruise is something that you will make a regular annual event on this special day. 

Sunset Cruise on Yacht Kingston

Step aboard the most intimate classic yachts in town to take in the spectacular New York City Skyline at Sunset! You and only up to 48 other guests will be aboard one of our 1920s style water taxis to zip out on to the Hudson in style! Our identical “mini yacht”, Kingston is the smallest and newest power yacht in the Classic Harbor Line fleet.

Wine & Cheese Pairing Classes on Yacht Manhattan

Each week wines are carefully selected from small family run or boutique producers to express the terroir of the region being represented. Years of experience, education and constant tasting help to select wines of exceptional value, quality and taste. Cheeses are ONLY artisan or farmstead cheeses sourced from NYC’s finest shops or small local dairies. Led by NYC wine pro Wendy Crispell (a certified wine and cheese educator) our wildly popular Wine and Cheese cruise has been featured in Wine Spectator, Time Out NY, Edible Manhattan, Gastronomista, Pasta’s Kitchen, Two plus Two review and The New York Post. (Photo by Tali Blankfeld). 

Evening Jazz Cruise

Cruise New York City’s famous harbor aboard the luxury 1920s style yacht Manhattan while listening to live jazz music by the Classic Harbor Line Jazz Trio, The Boat Band! Learn more about our NYC Jazz Cruise!  This is truly the perfect way to start your evening and relax to the soothing sound of the jazz. 

Sunset Cruise on Yacht Manhattan

Experience a beautiful New York City sunset and the illuminated cityscape during a comfortable and unique NYC Harbor sunset cruise through the Hudson and NY Harbor. Sit back and enjoy the gorgeous 360-degree view of the island from the open decks or the glass observatory of this Gatsby-esque 1920s style yacht. (Photo by Tali Blankfeld).

City Lights Cruise on Yacht Manhattan

Experience a Romantic New York Sightseeing cruise like never before. Step aboard our luxurious 1920s inspired motor yacht. Cozy up in the climate controlled observation cabin to take in the iconic sights. Join us for a bright and beautiful New York City Skyline by nightfall during a comfortable and unique New York City Harbor Cruise. This romantic cruise is truly one of the most spectacular ways to see NYC! (Photo by Tali Blankfeld). 

Full Moon Sail aboard Schooner Adirondack

Join us for a magical, moonlit view of Manhattan aboard the Schooner Adirondack. On this sail, you will experience the splendor of New York City’s nighttime skyline under the bright, radiating moonlight.

Full Moons 2020
May 7th: Flower Moon
June 5th: Strawberry Moon
July 5th: Buck Moon
August 3rd: Sturgeon Moon
September 2nd: Corn Moon
October 1st: Harvest Moon
October 31st: Blue Moon

City Lights Sail aboard Schooner Adirondack

Experience New York City lights like you never have on this sail past the bright and beautiful borough of Manhattan. You’ll take in the famous Manhattan skyline as it was meant to be seen — from the water. You will also enjoy spectacular views of Ellis Island, the Statue of Liberty, and the Brooklyn Bridge lit up by the evening lights.

Sunset Sail aboard Schooner Adirondack

See New York City sunset from the water on this evening sightseeing sail of the borough’s waterside landmarks. Climb aboard our beautiful 80-foot schooner, the Adirondack, and join your captain in this peaceful, picturesque sail away from the concrete and noise of the city. (Photo by Tali Blankfeld). 

Sunset Sail aboard Schooner America 2.0

Experience the most stylish means of viewing a New York City sunset; sailing aboard the Schooner America 2.0. While sailing you will be treated to a glass of champagne by our exceptional crew as you watch the vibrant warm rays of the sun sink peacefully into the horizon.  Step away from the hustle and bustle of the city with your favorite companions when you board this 105-foot, 1800s styled vessel, America 2.0. She’s perfect for romantic outings, entertaining friends from out of town, or just relaxing.

City Lights Sail aboard Schooner America 2.0

Board the 105-foot, 1800s styled, Schooner America 2.0 after dusk to take a tour of the unmatched Manhattan skyline. Bring your favorite companion or a group of friends to enjoy the lights as you sip on champagne in the peaceful late-night breezes of the Harbor. The City Lights sail on America 2.0 is an exquisite choice for an after-dinner event or to finish any day in the city. (Photo by Tali Blankfeld).