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

5.0 162 reviews

  • Avatar Jennifer Keife ★★★★★ 3 weeks ago
    Sometimes you wonder when a company has only 5 star reviews...this company does for a reason and it is beyond accurate and … More deserving. We booked a private 3 hour afternoon cruise for the end of May. Our Captain was Nick and his first mate was Julia...they were both beyond amazing. They were knowledgeable, engaging, helpful, accommodating and fun! We chose a private charter so it would be less stressful on my father who has some memory issues. He stayed on the boat the entire time but Nick was so great with him and Julia checked in with him often as well :). The other 6 of us had an amazing time snorkeling at the two different spots they took us. We were also fortunate enough to see a hammer head shark and lots of dolphins. This is was an amazing experience that all of us would do again. THANK YOU THANK YOU THANK YOU
  • Avatar Kelly Scott ★★★★★ a month ago
    We had a WONDERFUL experience today! We did the AM private charter and had fun snorkeling and sailing the ocean. The crew … More was knowledgeable and told us fun facts. Highly recommend this trip.
  • Avatar Rachel ★★★★★ 6 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!

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