The 7 Best Big Island of Hawaii Sailing Trips

1.Captain Cook Snorkel On A Power Catamaran With Lunch

★★★★★★★★★★5.0 · 2,232 reviews · 4 hours (approx.) · from $85Our pick

Cruise from Honokohau Marina to historic Kealakekua Bay on a power catamaran with Captain Aiden, Bryce, Jordan, or Kiwami. Snorkel among coral and fish, watch for dolphins and winter humpback whales, then enjoy sandwiches, fruit, snacks, and drinks before the coastal ride home.

“Super fun and knowledgeable! Very informative about the reef and marine animals. Staff was super friendly! Will definitely be coming back!”

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

★★★★★★★★★★5.0 · 797 reviews · 4 hours 30 minutes (approx.) · from $183

Set out from Kailua Pier on Body Glove’s large catamaran for about two hours at Red Hill, not Kealakekua Bay. You’ll get snorkeling gear, breakfast, BBQ lunch, reef-safe sunscreen, dolphin watching, a 20-foot slide, a 15-foot jump platform, floating toys, and attentive crew support.

“First class all the way. Crew was excellent, ship was excellent, and the location was perfect. Couldn’t ask for a better trip.”

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3.Afternoon Sail & Snorkel to the Captain Cook Monument

★★★★★★★★★★5.0 · 722 reviews · 3 hours (approx.) · from $136

Spend three hours aboard Sea Paradise’s afternoon boat from Keauhou Bay to Kealakekua Bay. Your crew guides you over coral and fish near the Captain Cook Monument, provides clean gear and flotation aids, and shares island history, marine life facts, and cultural traditions along the coast.

“The cruise was a lot of fun and supplied all the equipment needed for a great snorkeling adventure. The crew was informative and regarded safety as a high priority for those on board. We had an added bonus to see a pod of dolphins following the boat as we headed back to the harbor. Definitely recommend!”

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4.Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

★★★★★★★★★★5.0 · 695 reviews · 4 hours (approx.) · from $189

Join Kona Style at 8:30 a.m. for a four-hour sail on a 50-foot catamaran to Kealakekua Bay. Captain Dan and the crew share Hawaiian history, provide snorkel gear and instruction, and serve Kona coffee, breakfast, lunch, and non-alcoholic drinks.

“Absolutely beautiful boat and kind crew! We have been island hopping and this was one our favorite activities that we did!”

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5.Deluxe Sail & Snorkel to the Captain Cook Monument

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

Board Sea Paradise at Keauhou Bay for a 4.5-hour catamaran cruise along the Kona coast. Snorkel at Red Hill and Captain Cook Monument in Kealakekua Bay, with gear, reef-safe sunscreen, breakfast, lunch, snacks, and crew help included. Captains and crew share local stories along the way.

“Excellent Crew! Helpful and knowledgeable. Capt TRoy, Beau, Denali, Bailee, and Noe were the best, so much so that I will book another trip!!!”

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6.Deluxe Sail & Snorkel to the Captain Cook Monument

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

Sail from Keauhou Bay along the Kona coast aboard Sea Paradise’s catamaran. Snorkel near the Captain Cook Monument and, weather permitting, at Red Hill, with breakfast, lunch, gear, reef-safe sunscreen, and crew support included. The boat carries up to 44 people and returns by early afternoon.

“Nice crew, very clean boat and good breakfast and lunch. The snorkeling was just right, with two very different experiences, 45 minutes each”

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7.Waikoloa Signature Catamaran Sunset Sail

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

Board a barefoot 53-foot catamaran at Anaehoomalu Bay for a relaxed sunset sail along the Kohala-Kona coast. Captain Rob and crew may point out whales, turtles, lava fields, and mountain peaks while you enjoy cocktails, beer, wine, snacks, and wide sea views.

“Keith and the crew were really really really really really really really really really really awesome”

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