San Diego Proposal & Engagement Sails
Plan the perfect proposal or engagement party with downtown San Diego as your backdrop.
It Doesn’t Get More Romantic Than This.
This is a big moment. Let’s make it one to remember. Start your “happily ever after” story with us. Open water, clear skies, and a beautiful sailboat – the perfect setting to pop the big question or celebrate them saying, “Yes!” Go all out and add chilled champagne, keepsake flutes, and a San Diego Bay blanket to mark the occasion.
"My fiancee and I went out for an engagement photo shoot on the water. They went above and beyond even my high expectations!"
— Andrew E.
More Friends. More Fun.
Customize your sail for groups of up to 22 guests.
Your sail, your way. Cast off with the people who matter most on a spacious, premium sailboat – on your schedule. We'll even bring the drinks.
Anchor & Swim • Rady Shell Concerts • Catering & Bar Packages Available
Make Your Sail Delicious
Level up the occasion with gourmet bites from one of our incredible catering partners. Enjoy hors d'oeuvres or a full picnic meal.
Capture the Moment
Make the memories last forever with photos and videos from our preferred professionals. Note that photographers count toward your guest limit.
FAQs
We're Pretty Sure They're Gonna Say, "Yes!"
Will you help me keep the proposal a surprise?
Our crew has hosted many proposals and will be sure to keep things discreet and not spoil the surprise. Feel free to coordinate details with us before you sail.
Can I get flowers delivered?
Yes, you can have flowers delivered to our office beforehand. Address: 2720 Shelter Island Drive, San Diego, CA 92106. Just be sure to give us a call so the office staff is aware of flowers being delivered for your charter.
Can the captain take pictures of the proposal?
While the skipper’s primary role is to navigate and steer the boat safely, if they are able to, we can help coordinate for them to take photos on a mobile device.
Can I coordinate the timing of the proposal with the captain beforehand?
Please give our office staff a call at 619-297-7426 and we will take care of all of the details and coordinate with your skipper.
Am I able to have a photographer on board?
Yes. While we do not provide a photographer we have several you can book directly with. See above for a list of our preferred photographers and links to their contact information.
Is my photographer included in the passenger count?
Yes, the photographer would be included in the guest count on board.
