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

(Due to the COVID-19 pandemic and the need for social distancing, we are currently only offering private charters)

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
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
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

5.0 108 reviews

  • Avatar Tiffany Anderson ★★★★★ 2 days ago
    We booked a four-hour adventure with Captain Eric on Paradise Sailing for a family vacation. Honestly, I'm not sure … More it could have been a more perfect day. Eric, Yumi and Lila were probably some of the most kind and knowledgeable people we have ever met. It was like sailing with family! We boated alongside a group of five dolphins for nearly 45 min. (an experience my children will never forget), snorkeled in two separate locations, and sailed for part of the day. It was a perfect start to our Hawaiian vacation. We will definitely be coming back and booking Paradise Sailing again and recommending to all our friends! Thank you all so much!
  • Avatar Martha Vice ★★★★★ 3 months ago
    We had a wonderful 5 hour private charter trip! The owners were flexible, kind, professional, and fun! I would highly recommend … More them to anyone looking for a well organized and relaxing boat charter. We had the chance to see whales on our trip as well as some really fun snorkel spots. The boat is large and comfortable!
  • Avatar Joel Rubin ★★★★★ 4 months ago
    We had such a great day on the water with Eric and Yumi. They were friendly, professional, safety-minded, and just great … More people to spend 4 hours with. Their laid-back demeanor immediately helped remove the stress from our East-Coast bodies, as we saw whales, turtles, and even a shark during our outing.
    If you’re looking for a great way to spend the day on the water, give them a call. Guaranteed great time.

*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