THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Set sail with SailawayNY for a romantic dinner journey featuring iconic NYC landmarks, gourmet appetizers, and unmatched waterfront views. Discover the city from the water as you cruise past Lady Liberty and the Brooklyn Bridge.
Set sail with SailawayNY for a romantic dinner journey featuring iconic NYC landmarks, gourmet appetizers, and unmatched waterfront views. Discover the city from the water as you cruise past Lady Liberty and the Brooklyn Bridge.
Book with SailawayNY
Verified experiences and guided adventures in the surrounding area.
Operated by SailawayNY · New York, New York
New York City’s iconic waterfront offers more than just skyline views—it invites you aboard a sailing experience that blends cityscape drama with intimate moments on the water. SailawayNY’s Romantic Dinner for Two crafts a private journey starting from Chelsea Piers, gliding past the Statue of Liberty’s stern silhouette as you savor gourmet appetizers prepared onboard. The trip then threads the East River, bringing the Brooklyn Bridge’s soaring arches within arm’s reach as the sun dips low, setting the scene for a memorable dinner served under open skies.
This 1 hour and 45 minute sailing adventure is an exceptional way to experience New York’s unique urban wilderness from a waterborne perspective. The shifting panorama of Lower Manhattan’s architectural giants—gleaming glass towers and historic brick facades—animates the background while the gentle rocking of the boat brings a soothing natural rhythm to the evening.
SailawayNY stands out in the city’s outdoor recreation scene by melding classic sailing with curated dining, offering an experience that is both active and relaxing. The East River’s brackish currents and tidal flows create a distinctive aquatic environment, home to diverse birdlife such as ospreys and gulls, visible against the cityscape. This voyage layers cultural history—Lady Liberty herself representing freedom and opportunity—with the sensory pleasure of fresh breezes and artisanal cuisine.
Perfect for couples seeking a refined yet adventurous date night, the trip’s moderately paced itinerary balances scenery, conversation, and cuisine. Whether you’re a local or visiting New York City, this sailing dinner is a unique invitation to engage with the city’s waterways in a way few get to experience—intimate, scenic, and unforgettable.
easy.
1 hour and 45 minutes.
Suitable for all fitness levels; mostly seated during the trip with minimal movement on deck.
No sailing experience is needed; this trip is a guided experience designed for passengers of all backgrounds.
Dinner includes a gourmet meal prepared by the onboard private chef, served alongside appetizers as you sail.
Alcoholic beverages may be restricted; please confirm with SailawayNY directly before bringing your own.
This experience is tailored for two adults; please reach out to SailawayNY about special arrangements.
Trips may be rescheduled or refunded due to unsafe weather; SailawayNY provides guidance before your booking date.
Boarding takes place at Chelsea Pier 59 or Pier 60 in New York City.
The Statue of Liberty, a symbol of freedom since 1886, anchors this route, while the Brooklyn Bridge, completed in 1883, represents engineering innovation bridging boroughs.
SailawayNY emphasizes eco-friendly practices and supports local initiatives to maintain water quality and protect the river ecosystem.
SailawayNY operates private yacht and sailing charters in New York Harbor and surrounding waters. The company offers a variety of charter options aboard named vessels including the 60‑foot motor Yacht Trident (capacity up to 35 guests), the 50‑foot sailing Purse Princess, and the 40‑foot sailing Julia. Charter types listed by SailawayNY include weekday specials, motor yacht charters sized for groups from 2 to 35 guests, sailing charters with captain, romantic dinner cruises for two, marriage proposal packages, and private event charters for birthdays, weddings, and corporate outings. Motor yacht listings reference climate‑controlled interiors, premium bar selections, and gourmet dining prepared by a private chef on select trips. Several motor yacht packages note professional entertainment and state‑of‑the‑art sound systems. Sailing charters emphasize scenic routes along the Hudson and East River, past the Statue of Liberty and under the Brooklyn Bridge, offering distinctive views of the Manhattan skyline. Proposal packages described in trip summaries include champagne, roses, and a hidden photographer capturing images around the harbor. All captain‑led charters indicate operation with a licensed captain and crew. SailawayNY is featured on The Adventure Collective, where these charter products and trip summaries appear for discovery. Booking options span intimate two‑person experiences to larger 35‑guest celebrations, with motor and sailing vessels available to match event size and style. All details here reflect the trip summaries and vessel names provided in published listings.
Book with SailawayNY