Celebrate Molly’s 24th Birthday aboard the Clipper City, New York’s largest passenger sailboat, and experience stunning city skylines glowing at night from the harbor. A perfect mix of celebration and maritime ambiance awaits.
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Minimal physical exertion; suitable for all fitness levels
Wildlife
History
New York Harbor has long been a gateway to America, with sailing ships like the Clipper City carrying passengers since the 19th century.
Conservation
The Clipper City adheres to environmentally responsible practices to minimize impact on harbor waters and marine life.
Manhattan by Sail
Celebrate Molly’s 24th Birthday aboard the Clipper City, New York’s largest passenger sailboat, and experience stunning city skylines glowing at night from the harbor. A perfect mix of celebration and maritime ambiance awaits.
Manhattan by Sail operates passenger sails in New York, New York, offering public and private cruises aboard the Clipper City, New York’s largest passenger tall ship. The company’s scheduled experiences include Sunset Jazz sails, Afternoon Golden Hour Cocktail sails, Evening Wine & Jazz concerts, City Lights evening cruises, and daytime harbor sails. Private charters for celebrations and reunions are also available and listed events include birthday and class reunion sails.
Each itinerary sails through New York Harbor, passing signature landmarks such as the Statue of Liberty, Ellis Island, and the Brooklyn Bridge, with close views of the Manhattan skyline. Public trips advertised include a 90-minute Afternoon Golden Hour Cocktail sail and multiple evening jazz and wine cruises that combine live music and scenic harbor passages. The Clipper City features spacious wooden decks and a full bar with cocktails and wine; some offerings also note snacks and hors d’oeuvres during private events.
Manhattan by Sail markets both ticketed public excursions and privately booked events, providing options for couples, friends, and groups seeking skyline views or music-focused evenings. Trip summaries reference live jazz ensembles, wine selections, cocktail service, and photo-friendly sunset opportunities. Routes and featured experiences vary by departure, with specific sails emphasizing music, cocktails, or city lights.
All information on this page reflects listed trip summaries and locations for Manhattan by Sail as published for each advertised experience in New York Harbor. Ticket availability, pricing, and exact departure times are published with each trip listing. Check individual listings for booking details.
Location
New York, NY
Sails operate in New York Harbor
Trips Offered
8 Trips
Public and private listed experiences
Duration
Varied (including 90 min)
Some public sails are 90 minutes
Vessel
Clipper City
New York’s largest passenger tall ship
Check individual trip listings for departure times, ticket availability, and private charter options.
Book Early for Prime Deck Space
Reserve your spot in advance to secure a great view on the upper decks during sunset.
Dress in Layers
Evenings on the water can get cool even in summer; bring a light jacket or sweater.
Arrive 15 Minutes Early
Allow extra time for boarding to avoid missing the departure and enjoy a stress-free start.
Bring a Camera with Zoom
Capture close-up shots of landmarks and the city skyline illuminated after dusk.
Light Jacket
Keeps you warm against evening harbor breezes.
summer
Camera or Smartphone
For capturing scenic nighttime city views.
Comfortable Non-Slip Shoes
Ensures safety on the deck while moving around.
Reusable Water Bottle
Stay hydrated during the cruise, especially in warm months.