How long are the charters?

Charter lengths run two to six hours; choose a duration that fits your desired timing for sunrise, sunset, or a private evening cruise.

Can I bring alcohol or food?

Yes—guests may bring food and alcohol. If bringing glass bottles, inform the crew so they can chill beverages below deck and provide unbreakable sipping glasses for the top deck.

Are add-ons like photographers available?

Yes—professional photographers, flowers, and leis can be arranged as add-ons; coordinate details with the operator when booking.

Are there age or accessibility restrictions?

Not specified by the provider; contact the operator directly for accessibility accommodations or age-related questions.

Sail into Yes: Private Proposal Cruises off Oahu's Coast | Private | Sailing

Q: Where do guests meet the boat?

The meeting point is Kewalo Basin Harbor, 1125 Ala Moana Blvd, Slip C35, Honolulu, HI.

Q: What is the cancellation policy?

Customers receive a full refund or credit with 24 hours notice of cancellation.

On a private charter called Proposal aboard the Sailing Beauty, couples slip away from Kewalo Basin Harbor, 1125 Ala Moana Blvd, Slip C35, Honolulu, HI, for a tailored moment on the Pacific. The city shoreline slides past — Waikiki’s high-rises, the flanks of Diamond Head — while trade winds flatten the ocean into usable glass. Choose two- to six-hour options that let you time your ask for sunrise, golden hour, or under a starlit sky.

This is intimate, not theatrical: the crew on Sailing Beauty keeps the boat steady and the pacing quiet so your focus is on the ring and the person who will say yes. The vessel’s deck provides close contact with the water — reef gardens and the blue-green shoulder of the sea — and Hawaii’s marine life often appears unannounced: honu (green sea turtles) cruise nearby and spinner dolphins sometimes bow-ride. Add-ons such as a professional photographer, floral arrangements, or leis are available to match personal style and keep necessary details off your plate.

Geology and natural context sharpen the scene. Oahu’s shoreline here is a seam between volcanic bedrock and coral reef; offshore drop-offs deepen quickly, producing clear water and dramatic color shifts that photograph beautifully. The trade winds and long Pacific swell shape how a proposal unfolds—timing matters. The experience also brushes against local custom: presenting a lei after a proposal is a common Hawaiian gesture of affection and welcome.

Logistics are straightforward. Meeting point is Kewalo Basin Harbor, 1125 Ala Moana Blvd, Slip C35, Honolulu; charters run two to six hours; guests may bring food and alcohol, provided glassware policies are followed. The crew will substitute unbreakable sipping glasses and ice beverages on deck if you bring glass. Because the setting is a living ecosystem, guides emphasize reef-safe sunscreen and keeping a respectful distance from wildlife.

Why book? A private sail on Sailing Beauty turns a proposal into a lived scene rather than a staged photo, with ocean views that change by the minute and a small crew smoothing technicalities so you can stay present. For destination romance, Honolulu’s shoreline offers accessibility without sacrificing that suspended, away-from-the-world sensation that makes a proposal feel monumental. Whether you plan a quiet morning ask or a sunset surprise, this charter is designed to make the moment yours.

Booking is flexible: charters run two to six hours and customers receive a full refund or credit with 24 hours notice of cancellation. Coordinate timing with captain at check-in at Kewalo Basin Harbor to pick the best approach vector, and discuss add-ons like photographers or leis ahead of time so the crew can stage discreetly. The goal: one seamless, private moment in your story that opens onto the Pacific.