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
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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
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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

5.0 160 reviews

  • Avatar Rachel ★★★★★ 5 months ago
    Stunning sunset, awesome dolphins and whales, and an incredible boat ride! Our family of 8 adults and 5 kids (under 4 years … More old) had a great time on our sunset cruise. The owners were knowledgeable and so kind... and the boat was clean and sturdy. We even got to see 4 whales breech one after another after another! Our fam will talk about this trip for years to come. Thank you!
  • Avatar Denise Lafond ★★★★★ 11 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 Savannah Gehosky ★★★★★ 8 months ago
    Such a fun and beautiful experience! Highly recommend if you have a group of people that love snorkeling or sailing as Nick … More and Julia were a blast and knew all of the best spots! This was definitely the highlight of our trip!

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