Sailing Hawaii Catamaran Charters sailing Big Island Kailua Kona

Kailua Kona Sailing Catamaran Charters - Big Island Boat Tours

Enjoy a true sailing experience with a small number of passengers during a Kona sailing charter on Hawaii's Big Island! Our beautiful new sailing catamaran features plenty of shade, comfortable cushioned seating with tables, nice clean toilet facilities and the roominess, stability and speed of the newest 36' sailing catamaran offering Big Island boat tours.  We offer a variety of Kona sailing charters including a relaxing Kona Sunset Cruise and private catamaran charters.

Because we are family owned and operated, we provide the kind of personal service only a small business can and the comfort of catamaran sailing without the big boat crowds. Please check out our reviews on TripAdvisor to find out how much our guests enjoy sailing with us!

Our most popular Kona Sailing tours

Private Catamaran Tour4 Hour Private Catamaran Charter

Have our beautiful catamaran all to yourself and spend the morning sailing, snorkeling & looking for wildlife. Snorkel equipment and refreshments are provided. BYOB
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Big Island sailing tours kona sailing charters
Private Kona Sunset Cruise

Sail into the sunset aboard Kōlea on our Sunset Sail
and enjoy the beautiful Big Island Sunset.
Refreshments are provided.  BYOB
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Kona Sailing Charters sailing Big Island Hawaii


Starting at just $995*!

Have our beautiful sailing catamaran to yourself.
Where to go and what to do is completely up to you!
Snorkeling, Sailing, Sunset cruises, Weddings, sight seeing.
Private catamaran charter(*Rate for up to 8 guests for a 2 hour charter)
S/V Kōlea is USCG certified to carry up to 24 passengers

Google Rating

5.0 131 reviews

  • Avatar Brenda Hegel ★★★★★ a week ago
    Eric and Yumi made our birthday celebration sunset cruise so special!! Our group ranged in age from 70 down to 4 and everyone … More of us had a great time. When pilot whales were spotted, they answered our questions about the beautiful animals and sailed the boat at a safe distance but so we were able to see their beauty!! What a wonderful experience for all of us! Thank you.
  • Avatar Meghan Hupp ★★★★★ 7 months ago
    Very nice experience! Loved the crew! They were very personable and helpful, friendly, and just overall enjoyed the experience … More with them! The catamaran was very clean! They took care of everything, and even accommodated us when needed! Not to mention the sunset part of this cruise was spectacular! Definitely check them out if you are vacationing on the Big Island of Hawaii.
  • Avatar Michelle Van Beek ★★★★★ 4 months ago
    Wonderful day for our group! Highly recommend! We had a group of 14 including a bunch of small kids and the sailing, snorkelling … More and wildlife we saw was perfect. The boat was spotless and very comfortable. This was an excellent start to our big island vacay!

*Please note, for the protection of these beautiful creatures, we do not swim with wild dolphins.  Click Here for more information.

  • Paradise Sailing Hawaii

Paradise Sailing Hawaii, Honokohau Marina Slip J24, 74-380 Kealakehe Pkwy, , Kailua Kona, HI 96740, United States (US) - Phone: (808) 883-0399