BIG ISLAND

The 13 Best Big Island Sailing Tours

13 sailing trips  ·  from $89 a head

The good big island sailing tours fill up weeks ahead and the small boats go first. Below: the 13 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 $109

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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Kona Deluxe Catamaran Whale Watch - Following the Kona Coastline
Big Island Sailing Tours, Catamaran Sailing Trips, Catamaran Sailing Trips in the USA, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

Kona Deluxe Catamaran Whale Watch

8.Kona Deluxe Catamaran Whale Watch

★★★★★★★★★★4.5 · 55 reviews · 1 hour 30 minutes (approx.) · from $109

Review of Kona’s 90-minute whale watch on the Spirit of Aloha, with catamaran comfort, premium drinks, whale guarantee, price, and tips.

“Great crew! The whales cooperated and the coastline was gorgeous! Stan, John and James took good care of us!”

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Kona Tradewind Catamaran Day Sail - Leaving Honokohau Small Boat Harbor at 2:15 p.m.
Big Island Sailing Tours, Catamaran Sailing Trips, Catamaran Sailing Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours

Kona Tradewind Catamaran Day Sail

9.Kona Tradewind Catamaran Day Sail

★★★★★★★★★★5.0 · 42 reviews · 1 hour 30 minutes (approx.) · from $89Best value

Review of Kona’s 90-minute Tradewind Catamaran sail, with coastline views, drinks, wildlife chances, pricing, practical tips, and honest drawbacks.

“Captain Cindy and Louie were amazingly accommodating and friendly. We had such a great time and even got to take a jump into the water. We were treated like old friends and made to feel at home!”

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Kona Luxury Catamaran Yacht Snorkel & Sail - The Kona Coast and Its Possible Snorkel Stops
Big Island Sailing Tours, Catamaran Sailing Trips, Catamaran Sailing Trips in the USA, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Sailing Yacht Charters, Tour Reviews, USA Sailing Tours

Kona Luxury Catamaran Yacht Snorkel & Sail

10.Kona Luxury Catamaran Yacht Snorkel & Sail

★★★★★★★★★★5.0 · 40 reviews · 4 hours (approx.) · from $449

Review of Kona’s luxury six-person catamaran snorkel tour, with yacht comfort, lunch, dolphin sightings, costs, stops, and practical booking advice.

“Great cruise and snorkel experience staff on board were excellent and food/beverage was awesome! Great day on the ocean!”

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Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii - A Guided Snorkel of 50 to 60 Minutes
Big Island Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours

Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii

11.Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii

★★★★★★★★★★5.0 · 10 reviews · from $125

Review of Eka Canoe Adventures’ 2.5-hour Hawaiian sail and snorkel from Kona, with small groups, coastal views, gear, snacks, and practical tips.

“We had a great time with Eka canoe. The guys were super welcoming and seemed to really enjoy working there. We really appreciated the Captain sharing his knowledge on the islands history. It's a special place and it was very cool to see it from that angle.”

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Afternoon Tradewind Sail from Waikoloa - The 1:45 p.m. departure and meeting point
Big Island Sailing Tours, Sailing Tours, Tour Reviews, USA Sailing Tours

Afternoon Tradewind Sail from Waikoloa

12.Afternoon Tradewind Sail from Waikoloa

★★★★★★★★★★5.0 · 10 reviews · from $117

Review the Waikoloa afternoon tradewind sail, with Kohala Coast views, wildlife chances, beach boarding tips, price, and booking advice.

“Crew was wonderful. I'm older and have mobility issues but they helped me and made me feel special. Even though we saw no dolphins, even kids enjoyed the beautiful ride.”

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Waikoloa Turtle Catamaran Snorkel Sail - Snorkeling for beginners and regular swimmers
Big Island Sailing Tours, Catamaran Sailing Trips, Catamaran Sailing Trips in the USA, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

Waikoloa Turtle Catamaran Snorkel Sail

13.Waikoloa Turtle Catamaran Snorkel Sail

★★★★★★★★★★5.0 · 2 reviews · 2 hours (approx.) · from $149

Review of Waikoloa Turtle Catamaran Snorkel Sail, with turtle snorkeling, reef fish, open bar, snacks, costs, tips, and booking advice.

“Amazing experience on our snorkel trip this morning. The crew and captain were super friendly and knowledgeable. We took a short ride then were in the water for a good amount of time. We saw so many fish, urchins, a sea turtle and the beautiful reef. Then had a sandwich, snacks and drinks while enjoying the ride back to the bay. They even picked us up and dropped us back off at the resort. I would recommend to anyone looking for a snorkel trip!”

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