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 GOOGLE and 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
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 $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

5.0 154 reviews

  • Avatar Denise Lafond ★★★★★ 2 months ago
    Our family of 7 did the 4 hour private snorkeling and sailing trip near the start of our 10 day vacation on Hawaii. It was … More a great day for it and we were able to see pods of dolphins and flying fish during the trip. The catamaran was comfortable and immaculately clean. Captain Eric, Yumi, and first mate Julia were some of the most welcoming and helpful people we could have met during our trip. They gave us a ton of good recommendations on where to go on the islands. All the recommendations they gave us turned out to be top notch. We really started our trip out right by booking the sailing trip with them.
  • Avatar Harriet Echternacht ★★★★★ 6 months ago
    Our family of 8 had an exceptional 4-hour sail on the Kolea, Paradise Sailing’s private catamaran charter. Besides the great … More time sailing we were able to snorkel, fish and see whales and dolphins along the beautiful Kona coast with the snowy peaks of Mauna Kea and Mauna Loa in the background! It was a spectacular cruise with Captains Eric and Yumi and ship’s mate Daniel. We would love to do again and highly recommend it.
  • Avatar SD Surfmaps ★★★★★ a month ago
    Did the private 4 hr private sailing trip. Really great experience. Loved the snorkeling and saw a huge turtle that the kids … More didn’t stop talking about for the rest of the trip. Everyone loved laying out on the netting. Captain Tony and first mate Julia were great. If you are prone to motion sickness make sure you take some dramamine (ideally the night before). Definitely recommend this trip

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