Plan Your Perfect Engagement on the Water
Sophie Kaye
NYC Sailboat Proposal Guide & Checklist
charters starting at $600 for couples, $700 for 3-6 passengers
2 – 4 hours | flexible itineraries
catering menu | luxury amenities
Picture this: you’re getting down on one knee as the Statue of Liberty glows in the golden hour behind you, your partner is speechless, and a photographer is capturing every emotion. When proposal planning is used in advance, you’re free to focus on the moment itself.
Our complimentary concierge service guides you through everything—timing your departure to catch the perfect sunset, coordinating your photographer, and creating weather backup plans. Whether you’re envisioning an intimate moment for two with the Manhattan skyline at dusk or a champagne celebration under the Brooklyn Bridge with your closest friends, we’ll help you design a proposal that’s seamless, personal, and unforgettable.
Your Free Proposal Planning NYC Concierge
When you book a private sailboat charter for your engagement, you gain access to our dedicated proposal planning team at no additional cost. We’ve coordinated hundreds of successful on-the-water engagements throughout NYC, and we know exactly what transforms a good proposal into an extraordinary one.
What Our Proposal Planning Service Includes:
- One-on-one planning consultation to map out your complete vision and timeline
- Photographer recommendations and boarding coordination
- Route and timing consultation
- Decoration and catering coordination for champagne service, roses, and celebration packages
Our approach to proposal planning in NYC is simple: you focus entirely on the moment and the words you’ll say, while we handle every logistical detail behind the scenes.
These are just some of the considerations you may have:
Involving Family and Friends
One of your first decisions when planning a proposal in NYC: an intimate moment for two or a celebration with loved ones?
Private Proposal (Just You Two):
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- Maximum intimacy and privacy
- Easier to maintain a complete surprise
- Flexible, spontaneous pacing
- Celebrate with friends and family afterward at a favorite NYC restaurant
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Including Guests (Up to 6 Total):
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- Immediate celebration with your closest people
- Requires careful coordination to maintain surprise
- Consider separate guest boarding to preserve the surprise element
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Ideal Romantic Sailing Times
Golden Hour Magic: Sunset Departures
The most popular romantic boat ride option in NYC. Sunset departures capture the golden hour glow—that magical window when everything looks better, feels softer, and photographs beautifully.
For couples who thrive after dark, a night sail offers different magic. Watch Manhattan transform as skyscrapers blink on, bridges illuminate their architectural lines, and the Statue of Liberty torch holds court over the harbor. Quieter waters, cooler temperatures, and a romantic sense of having the harbor to yourselves.
Daytime Romance
Don’t discount daytime romance—some couples prefer the relaxed atmosphere and better visibility for photography. Added bonus: the couples weekday special will save you $100.
Charter Duration Recommendations
2 hours: Perfect for intimate proposals focused on the moment.
3 hours: Ideal for including guests. Allows relaxed pacing and multiple photo locations around the NYC harbor.
4 hours: Best for combining a proposal with a full catering experience or comprehensive sightseeing.
Ready to Begin Your Proposal Planning NYC?
Our concierge team is standing by to assist you in creating the perfect proposal experience. We handle every logistical detail so you can focus entirely on the moment that matters most. Your unforgettable proposal on the water starts here. Let’s plan something extraordinary together.
Complete Proposal Planning NYC Checklist
Use this comprehensive checklist to track your planning progress from booking through your engagement day:
☐ Book your charter date and time
- Reserve your preferred slot early—sunset departures book fastest during peak season (May-September)
- Choose charter duration: 2 hours (intimate), 3 hours (with guests), or 4 hours (extended celebration with dining)
☐ Schedule your complimentary proposal planning consultation
- Discuss your vision, timeline, and must-have elements with our concierge team
- Plan your ideal route and proposal location backdrop
☐ Book your photographer
- Book early—top photographers fill calendars 4-6 weeks out for weekend sunset slots
- Confirm they’re experienced with boat charters and comfortable on the water
- Discuss shot list: proposal moment, reactions, ring close-ups, couple portraits with skyline
- Coordinate arrival time at Pier 59 with your concierge
☐ Plan your music
- Create a proposal playlist
- Download music offline (cell phone reception can be spotty on the water)
- Consider the flow: background music during the sail, a meaningful song for the proposal moment
☐ Prepare what you’ll say
- Rehearse your proposal speech (though emotions may take over—and that’s perfect)
- Practice the physical mechanics: kneeling smoothly, opening the ring box, and presentation
- Run through your plan with a trusted friend if it helps calm nerves
☐ Decide on ring logistics
- Secure pocket option: Use a zippered/button pocket, test that the box doesn’t create an obvious bulge
- Consider a slim profile ring box (easier to conceal than traditional bulky boxes)
- Ensure the ring box opens smoothly—test it beforehand
- Trusted friend option: If bringing guests, someone can hold the ring until the moment
☐ Communicate with your partner (carefully)
- Let them know about the “boat ride” without revealing the proposal
- Mention the charter duration so they can plan their day
- Maintain mystery—keep anticipation building
☐ Review arrival logistics
- Parking: Chelsea Piers valet parking vs limited street parking
- Car service drop-off recommended at Pier 59
- If you’re strolling through the neighborhood to the pier, select your walking route
- Plan to arrive 15 minutes before departure time