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
Click here for more details.

Big Island sailing tours kona sailing charters
Kona Sunset Cruise

Sail into the sunset aboard Kōlea on our Sunset Sail
and enjoy the beautiful Big Island Sunset.
Refreshments are provided.  BYOB
Click here for more details

Kona Sailing Charters sailing Big Island Hawaii


Starting at just $795*!

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
(currently 11 guests max due to COVID 19 restrictions)

Google Rating

5.0 102 reviews

  • Avatar Nina McLaughlin ★★★★★ 4 weeks ago
    This private charter was the highlight of our trip to the Big Island. Yumi and Eric were so accommodating and gracious, … More the catamaran was in pristine condition and extra Covid precautions taken. We would book this excursion over and over again!
  • Avatar elle martins ★★★★★ 4 months ago
    Captain Eric and Yumi were extremely hospitable, attentive and were flexible with our group allowing us to choose what we … More wanted to do and when. The boat was very clean, they provided snacks, drinks and snorkel gear. They also allowed us to help put up the sails and even more unique was they found us a pod of dolphins, at one point we were surrounded by 50+ dolphins! Definitely a highlight of our trip in Kona.
  • Avatar James McCarthy ★★★★★ 9 months ago
    We were a party of five. We signed up for a 3 hour snorkel cruise, but mid-cruise extended it to a 4 hour cruise with some … More sailing added.
    Some of our group were experienced snorkelers and sailors. But no experience was necessary to enjoy the Paradise cruise. It was a perfect day on the water on Big Island. The boat was immaculate and well provisioned, the snorkeling sites were easy to access and full of interesting fish. The owners were friendly and informative. The sailing was a nice way to finish off the excursion. The owners provided all necessary snorkeling equipment as well as drinks and treats.
    I highly recommend Paradise Sailing. It was well worth the cost.

*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, 74-380 Kealakehe Pkwy, Slip J24, , Kailua Kona, HI 96740, United States (US) - Phone: (808) 883-0399