A mother-and-son team focused on calm, personal charters instead of crowded tour-boat experiences.
Private sailing charter Honolulu
Come Aboard Sailing Beauty.
Private sailing charters along O'ahu's south shore for sunset sails, proposals, weddings, special occasions, fireworks, and peaceful time on the water. Family-owned, easy to book, and designed for guests who want a beautiful escape at sea.
Your charter is for your guests, your pace, and the kind of day you actually want on the water.
Sail past Waikiki, Diamond Head, and the Honolulu coastline with sunset, city-light, and ocean views.
Sail With Us Today
Choose your private charter.
Customize your private luxury sail. Choose the time and adventure you wish to have here in Honolulu, then move straight into the booking link.
Proposal
Private sail designed around your moment.
Captain and crew are included, photographer add-ons are available, and the setting is built for a calm yes on the water.
Starting at$699
Wedding or elopement
Ocean views for a beautiful ceremony and timeless photos.
Private sail with ordained captain as officiant, captain and crew included, and a setting that keeps the day intimate from dock to sunset.
Starting at$949
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Special occasion
Celebrate birthdays, anniversaries, and meaningful moments on the water.
A private sail tailored to your celebration, with room to keep it simple or dress it up with thoughtful add-ons.
Starting at$699
Sunset sail
Picturesque views of Honolulu as the sun drops over the water.
This charter leaves in the late afternoon and returns just after sunset, with skyline, shoreline, and Ko'olau views throughout the sail.
Starting at$699
Friday fireworks sail
Golden hour, city lights, and fireworks from the water.
A special Friday night cruise along the Waikiki coastline that starts with golden light and ends with the Hilton fireworks show offshore.
Starting at$699
Ash scattering
A respectful private charter handled with care and intention.
Captain Donovan creates a sacred space for burial at sea and can make sure you have the location details needed for future visits.
Starting at$699
A peaceful sailing oasis
Sailing Beauty gained her name from her performance on the water.
She has sailed the oceans of the world, raced between the Hawaiian Islands, and has been utilized in chartering services both on the mainland and here on the coastline of O'ahu.
She has been beautifully transformed by her new owners with a refreshed deck, updated upholstery, and thoughtful comforts that make time on board feel polished without losing the calm spirit of sailing.
On board
Private, beautiful, and easy to step into.
The goal is simple: make it easy to picture the experience, book quickly, and feel confident about the people and the boat before you ever arrive at the dock.
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Looking For Something Else?
Being a small family-owned business allows us to be flexible.
If you are interested in a charter type or time that is not listed, give us a call or text at (808) 738-6604 and we will be sure to help plan the perfect charter for you.
Guest feedback
What guests remember after they sail.
Real reviews matter here because this is a customer-booking site. The goal is to make it easy for a guest to picture the experience and move into the right charter without hesitation.
"An unforgettable sunset charter with Captain Donovan on the Sailing Beauty. We enjoyed breathtaking views of Waikiki at sunset, spotted sea turtles, and relaxed on the water."Emma M.
"The boat itself is beautiful and very comfortable. The crew was warm, friendly, and accommodating. I would definitely recommend this experience."Ryan
"Words can't describe the beautiful scenery we enjoyed. Smooth sailing, great company and ono food embraced us with a sunset to top it all off."Charise J.
"Seeing Waikiki from the water as the sunsets is remarkable, an unforgettable experience."John S.
"A unique, well priced, luxury sailing experience. I look forward to joining them again."Ryan