New York, NY

Romantic Sails/Cruises

Romance in NYCTake to the water and fall in love all over again. There are a lot of romantic things to do in NYC, but the most unique romantic thing to do in NYC is step aboard one of our classic vessels for a unforgettable memory.

Take a deep breath, relax and feel the wind in your hair. Sip on Champagne and have a quiet, intimate conversation with your loved one as you drift by the Statue of Liberty or cruise below the Brooklyn Bridge. Sit aboard one of our yachts and have moments of laughter and take in the breath taking views. Whether it is a City Lights Cruise, Sunset Sail, Wine Tasting or Full Day trip to Bear Mountain you and your loved one will share an experience that will last a life time and you are sure to make this a regular date idea.


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.

  Depart: Chelsea Piers   Boat: America 2.0   Cost: Adult $68 - $78

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.

  Depart: Chelsea Piers   Boat: America 2.0   Cost: Adult $54

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.

  Depart: Chelsea Piers   Boat: Manhattan   Cost: Adult $52

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!

  Depart: Chelsea Piers   Boat: Manhattan   Cost: Adult $56

Champagne City Lights Cruise on Yacht Manhattan

Experience 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!

  Depart: Chelsea Piers   Boat: Manhattan   Cost: Adult $52

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.

  Depart: Chelsea Piers   Boat: Adirondack   Cost: Adult $68 - $78
  Depart: Brooklyn Bridge Park Marina   Boat: Adirondack   Cost: Adult $68 - $78

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.

  Depart: Chelsea Piers   Boat: Adirondack   Cost: Adult $54

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.

  Depart: Chelsea Piers   Boat: America 2.0   Cost: Adult $54

Sunset or City Lights 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.

  Depart: Chelsea Piers   Boat: Kingston   Cost: Adult $44
  Depart: Brooklyn Bridge Park Marina   Boat: Kingston   Cost: Adult $44

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!

  Depart: Chelsea Piers   Boat: America 2.0   Cost: Adult $124

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.

  Depart: Chelsea Piers   Boat: Manhattan   Cost: Adult $54

Gay Pride Fireworks Sail on Yacht Kingston

Step aboard Kingston 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 “ohs 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.

  Depart: Chelsea Piers   Boat: Kingston   Cost: Adult $68

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.

  Depart: Chelsea Piers   Boat: Adirondack   Cost: Adult $72

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.

  Depart: Chelsea Piers   Boat: America 2.0   Cost: Adult $72

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.

  Depart: Chelsea Piers   Boat: Manhattan   Cost: Adult $104

Holiday Wine Tasting aboard Yacht Manhattan

This fun, interactive NYC cocktail event features a different theme in cocktail culture each week. Craft liquors, house made fruit infusions, gourmet simple syrups and creative garnishes are used to create 5 different signature cocktails with a fresh new spin or traditional flavor. From historical cocktails to modern mixology with tales of distillers, a peek into past and present trends in popular drinks and recipes to recreate your favorite drink at home. Learn how to balance contrasting flavors, add depth of flavor, what makes each liquor unique and get tips on the best sources for ingredients and pairing spirits with food.

  Depart: Chelsea Piers   Boat: Manhattan   Cost: Varies

Cocoa and Carols/Holiday Jazz 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 90 minute cruise to see the New York City lights. Delicious Hot Cocoa, Cookies, and treats for all our guests are included!  This is a NYC Holiday cruise that you just can’t miss!

A live Jazz Trio will be playing Wednesdays, Fridays & Sundays, and Holiday Caroling will be featured Mondays, Tuesdays, Thursdays & Saturdays.

  Depart: Chelsea Piers   Boat: Manhattan   Cost: Adult $56 | Child $36

New Year’s Eve Fireworks Cruise

Join us in your finest formal-wear for a wonderful New Year’s Eve celebration aboard the Manhattan and experience a comfortable and unique waterways cruise around our City of Lights. Take in the New Year’s Eve Fireworks in our cozy enclosed back observatory. Start the night off with a Sparkling Wine Tasting and dance the night away!

  Depart: Chelsea Piers   Boat: Manhattan   Cost: Adult $346

Valentine’s Day Champagne & Aphrodisiacs Pairing Cruise

Celebrate this Valentine’s Day with your special someone on Classic Harbor Line’s Champagne and Aphrodisiac Pairing Cruise in New York City. As you cruise on the Yacht Manhattan, you and your loved one will be able to take in all the romance the New York skyline has to offer while cuddling up and staying warm in our climate controlled observatory. You will be treated to a four course pairing menu that is sure to entice.

  Depart: Chelsea Piers   Boat: Manhattan   Cost: Adult $76

August 22nd: Italy! Part Two.

Traditions in Wine and Cheese, Southern Italy, Sicily and Sardinia. Italy is home to fabulous array of wines with hundreds of indigenous grape varieties and cheese! Taste, compare and learn about the laws, traditions, perfect pairings and more in this special celebration of Italy!

  Depart: Chelsea Piers   Boat: Manhattan   Cost: Adult $104

September 12th: For Gouda time call, Chille & Argentina.

Chile and Argentina are home to fabulous and food friendly reds and whites! They may not have any indigenous grapes but vintners from Spain, France, Italy and the USA have banned together to set up second homes there. Find out why these bold beauties are gaining favor the world over! Pair these wines with a stellar selection of Gouda cheeses, aged from 6 months to 5 years! Discover why Gouda in all of its glory pairs perfectly with these sexy, full bodied, bodacious wines. These are no red waxed supermarket cheese’s, there are the real deal in deliciously addictive flavor!

  Depart: Chelsea Piers   Boat: Manhattan   Cost: Adult $104

September 26th: Portugal, It’s a treasure trove of delicious wines and cheeses!

Portugal is full of amazingly delicious red, white, sparkling and fortified wine. Famous for Port, cork production and one of the most successful wine marketing plans ever Portugal is moving into the future with modern techniques and flavor. Its cheese is also gaining a cult following with curd nerds everywhere. Learn about the grapes, styles, rennets, aging methods, regions and culture of Portugal. Swirl, sip, savor the amazing flavors and go home with a recipe for Wendy’s famous tomato jam (a traditional Iberian treat).

  Depart: Chelsea Piers   Boat: Manhattan   Cost: Adult $104

October 10th: Oktoberfest! Austria and Germany, Red and White Wines with Germanic cheeses and treats!

Fall in love with the flavors, aromas and taste of Riesling, St. Laurent, Blaufrankisch, Zweigelt and Sekt! Learn the terms to help you determine the taste and style of these wines. Discover the traditions, regions and modern advances in each country. Savor the amazing, stinky, aged wonders in the cheese world of Germany and Austria. NYC’s wildly popular “Summer of Riesling” may be over but these wine and cheese combinations are the perfect way to celebrate the flavors of Fall! Go home with a recipe for Wendy’s delicious Liptauer cheese!

 

  Depart: Chelsea Piers   Boat: Manhattan   Cost: Adult $104

October 16th: Spain and the Iberian Peninsula, From Rioja to Rueda and beyond with sinfully satisfying cheeses, jams and drizzles!

Immerse yourself in the culture of Spain! Sail away to a faraway place using sight, sound, smell and taste. Explore the culture, tradition, grapes, regions, cheese styles and tapas tradition of Spain. Learn about ancient traditions and modern advances in the world of Spanish wine. Taste the refreshing whites and rich reds, aged wines and finish with a luscious sherry! An interesting selection of cave aged cheeses will be paired perfectly. Go home with ideas for creative tapas and a special jam recipe!

  Depart: Chelsea Piers   Boat: Manhattan   Cost: Adult $84

November 14th – Craft the perfect platter for Holiday Celebrations!

Holiday Wine and Cheese Pairing with Chocolate and Chutney. Craft the Perfect Platter for Holiday Celebrations. Recipes Included! Is there a perfect wine to serve with a selection of cheese? Is there a specific order or style of cheese I should know about? Are there easy tips or tricks to make my display look amazing? Should I serve red or white? Are there any other choices beyond fruit to add interest? Go home with a handy pairing guide and a recipe for a delicious drizzle created by a master chef! International selection of wine and cheese will be served.

  Depart: Chelsea Piers   Boat: Manhattan   Cost: Adult $104

November 28th – Perfect pairings and ideas for light bites and cheesy dessert!

Holiday Wine Pairing. Wines to pair with everything on your holiday table, even your wacky relatives! Perfectpairings and ideas for light bites and cheesy dessert! Recipes Included! With so many flavors, personalities and choices at the holiday table picking the perfect wines can be a head spinning ordeal! Are there wines that will make everyone happy and still pair with a number of foods? YES! Learn about the 5 wines styles that will make your holiday celebrations a success! Go home with a recipe for a mini cheese inspired dessert that is easy and incredibly tasty!

  Depart: Chelsea Piers   Boat: Manhattan   Cost: Adult $104

December 12th – Holiday Wine & Cheese pairing with Chocolate and Chutney!

Holiday Wine and Cheese Pairing with Chocolate and Chutney, Craft the Perfect Platter for Holiday Celebrations. Recipes Included! Is there a perfect wine to serve with a selection of cheeses? Is there a specific order or style of cheeses I should know about? Are there easy tips, tricks and to make my display look amazing? Should I serve red or white? Are there any other choices beyond fruit to add interest? Go home with a handy pairing guide and a recipe for a delicious drizzle created by a master chef! International selection of wines and cheeses will be served.

  Depart: Chelsea Piers   Boat: Manhattan   Cost: Adult $104

December 19th – Wines to pair with everything on your holiday table, even your wacky relatives!

Holiday Wine Pairing. Wines to pair with everything on your holiday table, even your wacky relatives! Perfect pairings and ideas for light bites and cheesy desserts! Recipes Included! With so many flavors, personalities and choices at the holiday table picking the perfect wines can be a head spinning ordeal! Are there wines that will make everyone happy and still pair with a number of foods? YES! Learn about the 5 wines styles that will make your holiday celebrations a success! Go home with a recipe for a mini cheese inspired dessert that is easy and incredibly tasty!

  Depart: Chelsea Piers   Boat: Manhattan   Cost:

December 31st – Bubbly Holiday Tasting!

Sparkling Wines and Silky, Savory Cheeses for a Decedent NYE Celebrations! Sparkling wine is the most versatile pairing in the cheese world! Find out about the grapes, styles, traditions and methods of production. Tickle your senses with bubbly Cremant from France, Sekt from Austria, Cava from Spain, Method Ancestral Prosecco, an American bubbly from the oldest hand dug cellar in the states and discover an unusual sparkling red! Taste a runny, ripe bloomy rind, a cave aged reserve, a rock hard salty sheep’s milk cheese and other surprises in this fun, interactive tasting!

  Depart: Chelsea Piers   Boat: Manhattan   Cost: Adult $104