Romance Packages
About Our Romantic Sailing Packages on Long Island’s East End
Love deserves a setting worthy of the moment. SailSelinaNY specializes in romantic celebrations: engagements, anniversaries, vow renewals, honeymoons, birthdays, bachelorette parties, girls’ nights, and unforgettable date nights. Whether you’re planning a proposal or marking a milestone, our crew curates romantic sailing Long Island NY experiences that feel personal, thoughtful, and magical.
Feel the joy of giving the perfect gift: a two hour experience your sweetheart will always remember. Perfect for folks looking for a day trip from Long Island or NYC.
Our captain and crew are thrilled to customize your private sail.
Popular enhancements include:
Chocolate‑covered strawberries or artisan cheese trays with your BYOB bubbly
Bouquets of fresh flowers for proposals
Custom cakes for anniversaries or birthdays
Dessert samplers for two
Personalized keepsakes for surprise gift‑giving moments
From the first hello to returning to the dock, we curate an experience that feels effortless, elegant, and deeply memorable.
Romance sails are limited — book early for peak weekends.
A Private Sail That Feels Like Your Love Story
Your private charter takes place aboard our meticulously maintained 1926 classic wooden yacht built in Greenport and still sailing the local waters nearly 100 years later. With varnished mahogany, polished brass, and only six guests onboard, the setting is intimate, timeless, and cinematic.
Sail the serene waters of Shelter Island Sound, Greenport Harbor, and Long Island’s East End — some of the East Coast’s most romantic waterfront destinations.
Best of all, we’re:
A short ferry ride from the Hamptons and Montauk on the South Fork
A perfect day trip from Sag Harbor or Southampton
An easy getaway for NY and Long Island couples
Sailing away to celebrate love has never been easier.
Book early — peak summer romance sails sell out quickly.
Perfect Romantic Sailing Trips for Anniversaries, Honeymoons, and Proposals in Greenport & Shelter Island
Book Your Romantic Sail
Ready for the most intimate sailing experience on Long Island’s East End?
Choose a shared or private two-hour sail aboard SailSelinaNY, a 1926 wooden yacht handcrafted in Greenport and still family-operated today.