Sailing Hawaii Catamaran Charters sailing Big Island Kailua Kona

Kailua Kona Catamaran Sailing Charters Big Island Boat Tours

Enjoy a true sailing experience with a small number of passengers while sailing Hawaii in Kailua Kona! Our beautiful new sailboat 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 Big Island boat tours

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.
Light appetizers, tropical fruit juice and bottled water included. BYOB

$99 per adult, $69 for children ages 5 to 12
(4 and under no charge)

Private Catamaran Tour4 Hour Private catamaran charter

Have our beautiful catamaran all to yourself and spend the morning sailing, snorkeling & looking for wildlife. Includes all snorkel equipment.  Refreshments provided (fresh fruit, baked goods, soft drinks, tropical juice & bottled water) BYOB
Click here for more details.

Call us at (808) 883-0399
for more information about our Kona sailing charters

Kona Sailing Charters sailing Big Island Hawaii


Starting at just $895*!

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 95 reviews

  • Avatar L Kiss ★★★★★ a month ago
    Amazing sunset cruise! Eric and Yumi were fantastic hosts, the cheese, fruit, and nuts was really good. We saw so many … More dolphins swimming, breaching, and spinning on the cruise out. They kindly took pictures of the clients off the front and sunset offered opportunity to help manage the sailing ropes. The best parts were 1) the intimacy of the very small group, 2) the ability to bring your own beverages (we brought the IPA that we liked), and beauty of seeing dolphins and the sunset.
  • Avatar Mark Barnes ★★★★★ a week ago
    My wife and I took the 2 hour Sunset cruise and enjoyed it. The owner/operator husband and wife crew were great hosts, supplying … More light appetizers and non-alcoholic beverages, and the boat was clean and comfortable. We had a cloudy day so sunset was limited and very little wind so the boat operated under motor instead of sails. No matter, the trip was still relaxing. Thanks, Eric and Yumi!
  • Avatar Donna McGuire ★★★★★ 6 months ago
    We sailed twice with Paradise Sailing while we were on the Big Island; the sunset cruise and a private snorkel cruise for … More our party of 8. Both cruises were wonderful. The catamaran is spotless, cleanest one I've ever been on! The light snacks on the sunset cruise and the banana bread on the private charter were just the right extra to add to our cruises. Most importantly, the cruises were so relaxing! Eric and Yumi went above and beyond to ensure their passengers had a memorable time. I certainly recommend Paradise Sailing anytime you are in paradise!!

*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)