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Private Sailing Charter in Waikiki

Location: Waikiki, Oahu

Sail off of Waikiki Beach with Captain David during a Private Sailing Charter, where the spirit of exploration and adventure sails alive into the present day. Captain David holds 20 years of sailing experience and is ready to share his passion for the ocean with you along his private 34ft sailboat named, Running Silent.

From the serene mornings adorned with marine life under the majestic view of Diamond Head to the enchanting evenings painted with the hues of sunset, this exclusive tour offers an intimate connection with the ocean's wonders. Tailored for small groups, our sail provides a unique escape from the bustling crowds, allowing you and your loved ones to indulge in the tranquility and beauty of the sea. Whether you're steering the helm or lounging with the sails above, every moment is a promise of full sails and full smiles, making memories that last a lifetime.

Morning Sail

Your adventure begins at the Ala Wai Boat Harbor, conveniently located within walking distance from most Waikiki hotels. As the boat casts off, the cool morning air fills your lungs, and the sun's first rays illuminate Diamond Head in a warm glow. The ocean comes alive around you; dolphins leap joyfully, whales breach in the distance, and turtles glide beneath the waves. If the sea invites, you may even dive in for a snorkel, immersing yourself in the vibrant underwater world. For those eager to learn, Captain David offers a hands-on experience—take the helm, assist with the sails, or simply soak in the peaceful ambiance as we do the navigating.

Sunset Sail

As the day winds down, set sail again for an exclusive evening on the water. This time, the ocean greets you with a different palette, one of fiery oranges and calming purples as the sun dips below the horizon. Bring your favorite drinks and pupus (appetizers) to enjoy a picnic at sea, against the backdrop of Waikiki's glittering shoreline. On Fridays, the sky lights up with fireworks, adding a spectacular finale to your day at sea. The departure time is tailored to your preference, ensuring you catch the perfect view of the sunset and the evening's tranquil beauty.

Throughout your journey, aboard the Running Silent, comfort and intimacy are guaranteed. With ample seating for up to six, it's the perfect setting for families or friends seeking a private sailing experience. The boat's quiet electric motor ensures a serene sail, allowing the natural sounds of the sea to serenade you. Captain David's passion for sailing enriches the experience with stories and lessons, inviting you to try steering under his expert guidance.


  • Private charter aboard RUNNING SILENT, a 34-foot sailboat with electric motor
  • 20 year experienced and knowledgeable Captain
  • Option to participate in sailing or relax on board
  • Snorkeling opportunity (conditions permitting)
  • Cooler for BYOB drinks
  • Onboard bathroom facilities
  • Sailing playlist with option to play your own music
  • Educational insights into sailing theory and stories
  • Sightseeing (dolphins, whales, turtles, and other marine life depending on the season)


  • Maximum of 6 passengers to ensure a personal and comfortable experience
  • Bring sunscreen or long sleeves for sun protection during day sails
  • Light jacket recommended for evening sails as temperatures may drop
  • BYOB is welcome; however, excessive alcohol consumption is discouraged for safety
  • Children must be accompanied by adults


2 hours


Ala Wai Boat Harbor - 1651 Ala Moana Blvd, Honolulu, HI 96815

Cancellation Policy

Customers will receive a full refund or credit with 24 hours notice of cancellation. Customers will also receive a full refund or credit in case of operator cancellation due to weather or other unforeseen circumstances. Contact us by phone to cancel or inquire about a cancellation. No-shows will be charged the full price.