Romantic Sails/Cruises

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).

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) 

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). 

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 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 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 NY Harbor Cruise. This romantic cruise is truly one of the most spectacular ways to see NYC! (Photo by Tali Blankfeld). 

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). 

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. 

Classic Cocktails with a Twist aboard Yacht Manhattan

Savor a well-made cocktail as you watch the city pass by while relaxing in your private, partitioned seating area surrounded by large windows. Snap a few shots as we linger in front of the Statue of Liberty, explore the outer decks or stay cozy in your private nook; every vantage point offers the BEST VIEWS OF NYC. Welcome in a new era of 20s cocktails with a Sake Gimlet or a Grapefruit & Rosemary Rickey. Our sophisticated cocktail menu is packed with creative modern-day spins. Your first cocktail choice is on-the-house and additional cocktails are available for purchase.

Champagne & Cheese Pairing Cruise

Bubbles, Bites & New York City Sights! As you cruise on the Yacht Manhattan II or Yacht Manhattan, you will be able to take in all the beauty the New York City skyline has to offer while relaxing in our grand observatory. This cruise has limited capacity to create an intimate, comfortable and quiet NY Harbor cruise.

Evening Jazz Cruise

Cruise New York City’s famous harbor aboard the luxury 1920s style yacht Manhattan or Manhattan II 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 & 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 River. 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.

Sunset Cruise on Full Moon from Chelsea Piers

Step aboard one of the smaller more intimate wooden yachts of the Classic Harbor Line fleet and departs from Chelsea Piers for a cruise in New York Harbor at Sunset. Yacht Full Moon is equipped with comfortable seating and excellent views of the city skyline and New York harbor. Occasionally this cruise will take place on her sister ship the classic Yacht Kingston. This charming plumb-bowed mini-yacht features wrap-around seating to take in all the amazing views this city has to offer. Each excursion will feature a slow pass by the Statue of Liberty & Ellis Island. 

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.

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 2021
May 26th: Flower Moon
June 24th: Strawberry Moon
July 24th: Buck Moon
August 22nd: Sturgeon Moon
September 21st: Corn Moon/Harvest Moon
October 20th: Hunter’s Moon

Cocoa and Carols Holiday Cruise

Please join us for this special warm and cozy cruise with your friends, family, and all your loved ones during the Holiday Season. Step inside the toasty solarium in full holiday decor for a one hour and thirty minute cruise to see the New York City lights. Listen to Holiday Caroling backed by a live band and sing along to the classic holiday carols.  One complimentary drink of Beer, Wine, Champagne or Delicious Hot Cocoa (Spiked if you please), Cookies, and treats for all our guests are included! (**Additional Drinks are available for purchase)   This is a NYC Holiday cruise that you just can’t miss! 

Holiday Jazz Cruise

Step aboard our luxury Yacht Manhattan II in full holiday decor and join us for our romantic Holiday Jazz Cruise.  Enjoy this 1.5 hour cruise with your loved one and a glass of Champagne in hand.  See the city lights twinkle at night as you cozy up for an evening out in NY Harbor aboard a luxury yacht.  A complimentary beer, wine, hot cocoa (spiked if you please) or champagne from the bar is offered on all trips. Additional drinks are available for purchase.