Private Engagement & Marriage Proposal Sail | Long Island Yacht Charter – Greenport & Shelter Island
Quick Details
Greenport Village-Mitchell Park Marina
Shelter Island – Dering Harbor
📍 Departures
2 hours, longer sails available by request
🕓 Duration
Private for two (up to six available)
👥 Guests
Private for two (up to six available)
🍷 BYOB
Wedding marriage proposals, romantic engagements
🌅 Ideal For
Ask about our professional photographer add-on to capture the big moment!
❓Tip
Local florist available, let us arrange this for you or bring your own
🌸 Add-On
Custom playlists & proposal coordination available
🎶 Personal Touches
Hidden ring coordination + your preferred surprise setup
💍 Special Touches
Flowers, charcuterie, photography — just ask
🌹 Custom Options
📷 Photos
Crew discreetly captures the moment
Your Perfect Proposal Sail – Greenport & Shelter Island
The soft sound of sails in the breeze. The sunlight shimmering over the North Fork of Long Island’s East End. The person you love beside you, as you ask the most meaningful question of your life. Aboard SailSelinaNY, we specialize in creating unforgettable proposal experiences that are as unique as your love story.
Departing from Greenport Village or Shelter Island, you’ll glide along the water aboard our beautifully restored 1926 family yacht, built right here on the North Fork. With space for just six guests—and often booked privately for two—this is an experience designed for intimacy, elegance, and romance.
Limited availability — book early for peak weekends
How Your Romantic Long Island Engagement Sail Works
We’ll work with you to plan every detail—from timing your sail with the perfect sunset to helping you choose a secluded spot to drop anchor for the moment. You can bring your own Champagne, Long Island wine, or sparkling cider to toast after the proposal, and our crew will discreetly assist so everything unfolds seamlessly. Your captain and crew ensure everything flows smoothly—whether you’d like to play a favorite song, time the proposal with the sunset, or have flowers or candles waiting on deck. You can even coordinate with the captain in advance for timing, cues, or secret touches—we are experts at making sure your partner never suspects a thing.
Proposal Enhancements
Want to make it extra special? Add a photographer or local florist to capture and enhance your proposal. We’re happy to coordinate local partners from Greenport and Shelter Island who understand the magic of this moment. Or simply hand your phone to our helpful crew and let them capture the moment with a few snapshots of your momentus occasion.
Enhancements available upon request:
Professional Photographer – We coordinate with trusted Greenport & Shelter Island engagement photographers who specialize in capturing proposals aboard classic yachts.
🌹 Local Florist Arrangement – Partner with North Fork wedding florists for fresh, custom bouquets or onboard floral décor.
🎶 Personalized Touches– Add music, candles, or décor — we’ll help coordinate with local vendors to make it seamless.
A Proposal to Remember
After you’ve popped the question, enjoy a quiet sail along Shelter Island’s coastline, watching the colors change across the water. Toast to your future together and soak in the peaceful rhythm of the bay. Bring your favorite North Fork wine from nearby vineyards like Bedell Cellars, Kontokosta Winery, or Sparkling Pointe. Toast your engagement as the sun sets over Shelter Island waters and the shores of the North Fork of Long Island, NY.
When you return to shore, enjoy dinner at one of Greenport’s romantic waterfront restaurants to complete your perfect engagement day.
Noah’s www.chefnoahs.com
Port Waterfront Bar & Grill www.portbarandgrill.com
The Frisky Oyster www.thefriskyoyster.com
Why Choose SailSelinaNY
Exclusive & Private
Just you, your partner, and the open water.
Authentic Experience
Sail aboard a historic 1926 yacht, handcrafted in Greenport and still family-owned and loved after 100 years.
Scenic Beauty
The perfect proposal backdrop—Greenport Village, The East End, Shelter Island, and Long Island’s North Fork coastline.
Customizable:
Choose your favorite music, local wine, flowers, or photographer. Every proposal is unique.
Every love story deserves a setting as timeless as the sea. Let SailSelinaNY help you write the first chapter of your forever. Private for two — your yacht, your love story.
Ready to create this moment that will last a lifetime?
👉 Book Your Sail Now
or Call 📞 631-500-0763 to start planning your Private Engagement & Proposal Sail today.