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 $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

5.0 117 reviews

  • Avatar Tiffany Anderson ★★★★★ a month 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 Christopher ★★★★★ a week ago
    Very nice time. BYOB, did a sunset cruise, just two of us. Got a lot of ideas for restaurants in the age of 50 percent … More occupancy. Boat was safe and in good condition. A married couple, the owners, crewed the boat, and were very warm and accommodating. Best thing for perfect sunset pics.
  • Avatar Lake Rucker ★★★★★ a month ago
    You will not regret it. Our family of nine took a beautiful 4 hour snorkel trip with Capt Eric and Yumi. They were warm, … More helpful, knowledgeable about the area and the catamaran was pristine. They took us to the best snorkel spots, pointed out fish and shared many recommendations for local food and fun. They provided healthy, tasty snacks and soft drinks. If our family ever has the opportunity to travel to the Big Island again, we will certainly reach out to Paradise Sailing.

*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