Sailing

BIG ISLAND

Best Sailing On The Big Island

Ranked by traveller popularity

The 10 most popular sailing on the Big Island. What they actually deliver, who runs them, and what they cost.

10 Best Sailing On The Big Island

Big Island: Captain Cook Snorkel On A Power Catamaran With Lunch

Big Island: Captain Cook Snorkel On A Power Catamaran With Lunch - Where You Meet, What You Carry, and Why It Feels Smooth

Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona

Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona - Timing and Where You’ll Be Waiting (The Pier Part You Can Control)

2.Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona

5.0

Luxury catamaran snorkeling and dolphin watch from Kailua-Kona with included meals, reef-safe sunscreen, and fun water toys.

“Wow! I have been on two other snorkel trips and none compared to this experience. The food they provides was amazing, the boat was so much fun (they had so many fun things to swim with during our snorkeling time like a paddle board and yoga mat) and the crew was awesome. I highly recommend…”

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Waikoloa Signature Catamaran Sunset Sail

Waikoloa Signature Catamaran Sunset Sail - Kohala–Kona Coast Sights: Lava Fields, Turtle Chances, Volcanic Peaks

3.Waikoloa Signature Catamaran Sunset Sail

4.5

Waikoloa Signature Catamaran Sunset Sail on a barefoot 53-foot catamaran with live narration, premium drinks, and Kohala-Kona sunset views for $159.

“Great sunset sail. Absolutely beautiful, calming and relaxing. The crew was extremely nice and courteous.”

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Kona Signature Catamaran Sunset Sail

Kona Signature Catamaran Sunset Sail - Where the cruise goes: Kailua-Kona and Honokohau Marina

4.Kona Signature Catamaran Sunset Sail

5.0

Kona sunset catamaran with a full premium bar, snacks and a real dinner, plus chances to spot dolphins and whales.

“Very friendly staff and most accommodating. Answered all my questions! Thoroughly enjoyed our 90 minute experience - would highly recommend!”

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Kailua-Kona: Captain Cook Reef Catamaran Day Trip with Lunch

Kailua-Kona: Captain Cook Reef Catamaran Day Trip with Lunch - Captain Cook Monument: a meaningful stop that’s easy to enjoy

5.Kailua-Kona: Captain Cook Reef Catamaran Day Trip with Lunch

4.8

4-hour catamaran day trip from Kailua-Kona to Captain Cook Reef with lunch, snacks, and optional snorkeling at Kealakekua Bay.

“Bryce and Aleyo were wonderful guides. They have great personalities and made our snorkeling trip aemorable experience. I loved the tunes they were blasting during the ride to and there were also some educational moments as they showed us some key sights on our trip back to the harbor.”

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Waikoloa Catamaran Snorkel Sail Including Lunch

Waikoloa Catamaran Snorkel Sail Including Lunch - The 3-Hour Catamaran Rhythm (Fast, Not Rushed)

6.Waikoloa Catamaran Snorkel Sail Including Lunch

4.5

3-hour Waikoloa catamaran snorkel from Anaeho'omalu Bay with guided reef time, full premium bar, and deli lunch for fish, turtles, and possible dolphins.

“Great staff. Very accommodating and knowledgeable. Captain Jack put everyone at ease w his humor. The actual snorkeling was great quality. A good variety of fish and coral/plant life. Thoroughly enjoyed the trip and wanted to turn around and do it again.”

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Kona Catamaran Snorkel Sail with Lunch

Kona Catamaran Snorkel Sail with Lunch - Spirit of Aloha Catamaran: Shade, Space, and a Real Restroom

7.Kona Catamaran Snorkel Sail with Lunch

5.0

Sail the Kona Coast on a small catamaran, snorkel with provided gear, and enjoy lunch plus a full premium bar in about 3 hours.

“We did not see turtles but the friendliness of the crew made up for that. It was an especially nice cruise since we were the only 2 on the catamaran. We had our own private sailing!”

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Waikoloa: Catamaran Sunset Sail with Cocktails

Waikoloa: Catamaran Sunset Sail with Cocktails - Key things to know before you go

Sunset Cocktail Cruise on our Sailing Catamaran

Sunset Cocktail Cruise on our Sailing Catamaran - Catamaran space: sitting, standing, and even getting your feet toward the view

Kona Deluxe Catamaran Whale Watch

Kona Deluxe Catamaran Whale Watch - How the cruise works: sailing between Kona and Honokohau

10.Kona Deluxe Catamaran Whale Watch

4.5

Kona catamaran whale watch with humpbacks, premium drinks, and a free return if you miss sightings, sailing from Honokohau.

“Seeing false killer whales was awesome! Crew was knowledgeable and personable. Great 1.5 hours on the water in beautiful Hawaii!”

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