IT'S TIME FOR THE VACATION OF YOUR DREAMS
1/2 day, one-day, sunset, dinner, multi-day to multi-week inter-island vacation, and trip options are available.
Your Private Charter Experience
Experienced Crew
Your captain and crew bring firsthand knowledge of Hawaii’s waters, weather patterns, and seasonal marine activity. That local expertise helps create a smoother, safer day while guiding you toward quieter stretches of coastline and the best conditions available.
Luxury Comfort Onboard
Every vessel is selected for both performance and comfort. Spacious decks, shaded seating, open-air lounging areas, and easy ocean access create a more enjoyable experience from departure to return.
Flexible Itineraries
One of the biggest advantages of private yacht charters is flexibility. If your group wants more time snorkeling, a slower scenic cruise, or a route adjusted for calmer water, the day can evolve naturally around your preferences.
Snorkeling and Wildlife Encounters
Some of the most rewarding moments in Hawaii happen offshore. Depending on season and location, guests may snorkel above vibrant reef systems, spot green sea turtles, watch spinner dolphins, or witness humpback whales during winter migration.
Contact us and plan your next private sailing experience with Hawaii Sailing Adventures LLC.
Why Choose Hawaii Sailing Adventures
Many of Hawaii’s most memorable coastlines, quiet anchorages, and clear snorkeling waters are best reached only by private boat. That is what makes a yacht charter with Hawaii Sailing Adventures LLC different.
We do more than take guests out on the water. We help you experience the islands through local sailing knowledge, seasonal awareness, and access to places many visitors never see. From the Na Pali Coast to Lanai, Molokai, and the Kohala Coast, every route is shaped by ocean conditions, visibility, and the type of day you want to have.
Unlike larger tour operations, our private yacht charters and sailing vacations are built entirely around your pace. Spend the morning snorkeling in calm water, linger longer at a scenic cove, or cruise into the afternoon for a sunset view offshore. Your time on the water stays personal, relaxed, and completely focused on your group.
Hawaii Sailing Adventures offers private boats, catamaran charters, and sailing trips on our luxury fleet. We provide charter options for Maui, Kaanapali, Kauai, Niihau, Lanai, Molokai, Honolulu, Waikiki, Oahu, Kaneohe Bay, and The Big Island. Snorkel, whale watch and visit Napali Coast, Kaanapali & Kohala Coast, exploring the beautiful "unknown" Hawaii through our one of our luxury boat trips.
Contact us to learn more about booking a private catamaran or boat charter where you'll create a memorable adventure for your family and friends. Enjoy extraordinary encounters with whales, dolphins, and sea turtles, swim and snorkel in tropical island waters and have the best sailing experience in your lifetime!
Explore Our Fleet
- All
- Catamarans
- Sailboats
- Yachts
Ready to find out more?
Get information on prices, itineraries, private daily or weekly charters & tours in Hawaii.
Napali Coast, "The Forbidden Island", North Shore Molokai, Kanaapali, Manele Bay
Niihau, Kalalau Valley, lagoon, reefs and beaches, sea cliffs, waterfalls, snorkel, scuba, swim, sunbathe, kayak, paddleboard, surf, windsurf, fish, and dine ashore. Stay in the harbor as a pleasant, charming, quiet, relaxing home base with all the cooking and sleeping amenities, a more creative environment than a hotel or house, and explore on-island activities on a week or two sailing charter. Relax, work the sails, whale watch, extended inter-island trips, short sailing tours, sunset sail, and dinner cruise. Feel what it is like to offshore cruise in the most dramatically beautiful settings in the world. Our crewed sailing and luxury yacht charters and boat tour prices include skipper, food, fuel, gear, other vessel costs, Sail Blue Hawaii, and much more.