Romantic Sails/Cruises

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). 

Champagne City Lights Cruise on Yacht Manhattan

Experience a Romantic New York Sightseeing cruise like never before. Step aboard our luxurious 1920s inspired motor yacht. As you cozy up in the climate controlled observation cabin to take in the iconic sights, enjoy a complimentary. drink. (Enjoy a complimentary beer, wine, champagne or soda on us. Cash bar available for additional drink purchases) 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). 

Evening Jazz Cruise

Cruise New York City’s famous harbor aboard the 1920s style yacht Manhattan while listening to live jazz music by the Classic Harbor Line Jazz Trio, The Sound Waves! Learn more about our NYC Jazz Cruise!

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.

Live Jazz City Lights 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.  This sail is perfect for date night or a group of friends looking to do something unique.

Champagne 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 East Rivers. 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). 

Morimoto Sushi and Sake Sail on America 2.0

This light dinner sail features a most seaworthy cuisine:  sushi, and not just any sushi, but Iron Chef Morimoto’s sushi! No sushi meal would be complete without sake, and this sail does not disappoint, we offer a range of cool, refreshing sake served on the decks of New York City’s most elegant schooner. The menu includes a sampling of sushi perfect for a one-of-a-kind sunset sail – 9 sushi pieces and 1 roll – served in 2 platings, paired with 4 sake flights, and all while we set sail for the New York Harbor!

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.

Brews of the Boroughs Sunset Sail on Adirondack

Join us for a NYC Beer and Cheese Tasting sunset sail aboard the Schooner Adirondack.  Cruise in NY Harbor and let our crew cater to you with the most impeccable hospitality.  On this 2 hour sail you be served up to 4 locally made beers, expertly paired with artisanal cheeses by our in-house Executive Chef and Cheese Master. On this NYC Beer and Cheese Tasting sunset sail you will also take in the stunning views that NY Harbor has to offer and glide by the Statue of Liberty, Ellis Island and have the most famous skyline in the world as the backdrop for your next selfie!   

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). 

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 exquisite choice for an after dinner event or to finish any day in the city. (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 Moon Sail aboard Schooner America 2.0

Join us for a magical, moonlit view of Manhattan aboard the Schooner America 2.0. On this sail, you will experience the splendor of New York City’s nighttime skyline under the bright, radiating moonlight.

Around Manhattan Brunch Cruise

Join us for our famous leisurely weekend brunch! Our “cruisine” is packed with delicious foods & fresh baked goods! Our chef is aboard throughout the cruise, refreshing the buffet with fresh baked quiche, sausages, a spiral ham, spring salad, bagel & lox station, and waffle station. Guests are treated to a complimentary Bloody Mary or Mimosa as well! View the sites and enjoy a lightly narrated tour from the Manhattan’s climate controlled, glass observatory.

“This Cruise can be purchased at a reduced rate excluding food at $68. To obtain these tickets call 212.627.1825 Opt 4.“

Gay Pride Fireworks Sail on Schooner Adirondack

Step aboard Adirondack on Gay Pride night for the best seat in the house to take in the famous Pier 54 Fireworks! This annual celebration will end with a bang! Colorful fireworks soar in the sky of New York City Harbor just off Pier 54 after the “Pride Dance”. Exhale your “ooooo and ahs”! And watch as these electric volcanoes burst and fountains of sparkles fade into the open air above you as you glide through their reflections on the water.

Gay Pride Fireworks aboard America 2.0

Step aboard any of Classic Harbor Line’s fleet on Gay Pride night for the best seat in the house to take in the famous Pier 54 Fireworks!  This annual celebration will end with a bang!  Colorful fireworks soar in the sky of New York City Harbor just off pier 54 after the “Pride Dance”. “ooh” and “ah” as these electric volcanoes burst and fountains of sparkles fade into the open air above you as you glide through their reflections on the water.

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 1.75 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.  

Holiday Jazz will take place on Wednesdays, Fridays and Sundays.  

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 forty five 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.  Delicious Hot Cocoa, Cookies, and treats for all our guests are included!  This is a NYC Holiday cruise that you just can’t miss!

Cocoa and Carols Holiday Caroling will be featured Mondays, Tuesdays, Thursdays & Saturdays.

Holiday Wine Tasting aboard Yacht Manhattan

Step aboard the Yacht Manhattan or Manhattan II decked out in full holiday decor. Relax in our climate controlled glassed-in observatory and sip on wines hand picked by our adored wine expert Wendy Crispell!  She will teach you which wines go perfectly with everything on your holiday table. Additionally, each will be paired with the perfect cheese, chocolate or chutney to help you build the perfect holiday platter, or to help bring you into the spirited holiday season.

New Year’s Eve Fireworks Cruise

Enjoy a short champagne/sparkling wine tasting class at boarding to set the celebration in motion with our wine expert, Wendy Crispell.  Throughout the night, enjoy passed hors d’ oeuvres, our Live Jazz Trio the “Sound Waves”, and the New York Harbor Fireworks at midnight aboard our intimate and elegant 1920s style yacht.  So step aboard and celebrate the New Year with us in NY Harbor!

Champagne Valentine’s Day 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 lit-up 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 city lights 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.