Paradise Sailing Hawaii

Kailua Kona Sailing Charters Big Island of HawaiiKailua Kona Sailing Charters
on the Big Island of Hawaii

Harness the power of the wind and experience the natural beauty of Hawaii under sail! 

Now open in Kailua-Kona Hawaii!  A new Kona sailing charter on the Big Island for those who want to REALLY SAIL. Relaxing hands-on sailing with a small number of passengers, PLENTY OF SHADE, nice clean toilet facilities, comfortable cushioned seating with tables and the roominess, stability and speed of the BIG ISLAND'S NEWEST 36' SAILING CATAMARAN.  We offer Big Island Sunset Cruises and Private Charters for Snorkeling, Dolphin & Whale Watching.  Family owned and operated, we provide the kind of PERSONAL SERVICE only a small business can, a hands-on sailing experience to anyone interested 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 charters

Big Island sunset cruise kona sailing
Big Island Sunset Sailing Cruise

Sail into the sunset aboard Kolea, and enjoy the magic of
the Big Islands best Sunset.

Appetizers, tropical fruit juice and bottled water included. BYOB 

$94 per adult, $62 for children ages 6 to 12
(5 and under no charge)

Click here or call direct for on-line special $5 off!

Private Charters Kona Sailing Catamaran Big Island
 Private Snorkel Sail & Dolphin Watch

Have our beautiful catamaran all to yourselves and spend the morning sailing, snorkeling & dolphin watching.

Includes all Snorkel equipment.  Fresh fruit, baked goods, tropical juice & bottled water are provided. (Lunch and additional snacks are provided during the 4 hour private charter) BYOB

3 and 4 hour options.

Call us at (808) 883-0399
for more information

Kona Sailing Private Charters on Big Island of Hawaii


Starting at just $595*!

Have our beautiful sailing catamaran to yourself.
Where to go and what to do is completely up to you!
Snorkeling, Sailing, Dolphin & Whale Watching. 
CLICK HERE for more information.
(*Rate for up to 6 guests for a 2 hour charter)
S/V Kōlea is USCG certified to carry up to 24 passengers

Call us at

(808) 883-0399


Paradise Sailing Hawaii, 74-380 Kealakehe Pkwy, Slip J24, Kailua Kona, HI 96740, United States (US)

  • Paradise Sailing Hawaii