BIG ISLAND

The 7 Best Big Island Sailing Tours

7 sailing trips  ·  from $109 a head

The good big island sailing tours fill up weeks ahead and the small boats go first. Below: the 7 to book early, what each includes and how they differ.

Afternoon Sail & Snorkel to the Captain Cook Monument - What the snorkeling is like
Big Island Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours

Afternoon Sail & Snorkel to the Captain Cook Monument

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure - The 8:30 a.m. start and check-in routine
Bay, Harbour and Coastal Sailing, Big Island Sailing Tours, Coastal Sailing Tours in the USA, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

Deluxe Sail & Snorkel to the Captain Cook Monument - Leaving Keauhou Bay at 8:15 a.m.
Big Island Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours

Deluxe Sail & Snorkel to the Captain Cook Monument

3.Deluxe Sail & Snorkel to the Captain Cook Monument

★★★★★★★★★★5.0 · 535 reviews · 4 hours 30 minutes (approx.) · from $177

Review of Sea Paradise’s Kona sail and snorkel to Captain Cook Monument, with two reefs, meals, gear, coastline views, price, and practical tips.

“The crew and captain were wonderful, very helpful! The lunch and drinks were great. We really liked the sailboat, it was beautiful and it was fun to write on it. The first snorkeling spot was pretty boring. Captain Cook monument had the most amazing snorkeling ever!. Wish that we'd gone with the shorter tour and saved money because it wasn't worth it to go on a longer tour just to snorkel in that first spot.”

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Deluxe Sail & Snorkel to the Captain Cook Monument - Leaving Keauhou Bay at 8:15 a.m.
Big Island Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours

Deluxe Sail & Snorkel to the Captain Cook Monument

4.Deluxe Sail & Snorkel to the Captain Cook Monument

★★★★★★★★★★5.0 · 472 reviews · 4 hours 30 minutes (approx.) · from $179

Sail from Keauhou Bay to Captain Cook Monument for guided snorkeling, island views, breakfast, lunch, and two reef stops.

“Amazing experience! Surprised by a school of dolphins while snorkeling! Crew was super knowledgeable and friendly and made us feel safe while exploring! Highly recommend this trip!”

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Waikoloa Signature Catamaran Sunset Sail - A 53-foot catamaran with room to move
Big Island Sailing Tours, Catamaran Sailing Trips, Catamaran Sailing Trips in the USA, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Waikoloa Signature Catamaran Sunset Sail

5.Waikoloa Signature Catamaran Sunset Sail

★★★★★★★★★★4.5 · 396 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $159

Review of Waikoloa’s sunset catamaran sail, with coast views, drinks, boarding tips, food details, pricing, timing, and practical advice.

“We had a great cruise. The crew was terrific. We enjoyed the catamaran. The drinks were varied and the dinner was a surprise.”

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Afternoon Sail & Snorkel to the Captain Cook Monument - What the snorkeling is like
Big Island Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours

Afternoon Sail & Snorkel to the Captain Cook Monument

Kona Signature Catamaran Sunset Sail - What the 90-minute route actually offers
Big Island Sailing Tours, Catamaran Sailing Trips, Catamaran Sailing Trips in the USA, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Kona Signature Catamaran Sunset Sail

7.Kona Signature Catamaran Sunset Sail

★★★★★★★★★★5.0 · 218 reviews · 1 hour 30 minutes (approx.) · from $109Best value

Review of Kona’s 90-minute sunset catamaran sail, with coastline views, cocktails, dinner, wildlife sightings, practical tips, and value advice.

“Read email they send to tell you where to meet, coordinates are helpful. We met Captain Michael and crew: John and Caesar. They were kind and helpful especially without our sea legs. We sat and were served drinks and a surprise meal. We saw dolphins and a beautiful sunset. A memorable part of our trip.”

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