Proposal sail from $699
Price does not include taxes or crew gratuity* Call or text 808-738-6604 Book now
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Proposal charters

Private sailboat proposals in Honolulu.

A peaceful private sail designed around the question, the light, and the moment after. The route stays simple so the experience can feel calm, personal, and easy to book.

Engagement ring and bouquet on deck during a proposal sail aboard Sailing Beauty.

Why couples book this charter

A calm setting for one of the most important questions you'll ask.

The proposal charter is designed to keep the experience private, peaceful, and easy to personalize. Book it as-is, or add a photographer, leis, or a charcuterie board if you want more built into the day.

Starting at $699
Duration 2 hours
Departure Dock C, Kewalo Basin

What's included

Everything needed for a smooth, beautiful proposal sail.

Private sail

Your charter is reserved for your guests only, so the moment stays personal from departure to return.

Captain and crew

Experienced crew on board to run the sail and keep the experience feeling easy and calm.

Light refreshments

Water and light refreshments are included so you do not need to over-plan the basics.

Ocean views

Ocean, skyline, and shoreline views make this a strong fit for couples who want timeless photos afterward.

Available add-ons

Meaningful finishing touches if you want them.

Professional photographerstarting at $250
Charcuterie board$100
Flower leis (set of 2)$60
Premium flower leis (set of 2)$100

Planning notes

Keep the plan simple and let the sail do the work.

  • Arrive 20 to 30 minutes early at Dock C for check-in.
  • This is a barefoot charter, so shoes are stowed before departure.
  • You are welcome to bring your own food and drinks on board in addition to the included refreshments.