The 13 Big Island Sailing Tours We Would Step Aboard

1.Afternoon Sail & Snorkel to the Captain Cook Monument

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

From Keauhou Bay, you ride along Kona's lava coast to Kealakekua Bay, where a guide leads a one-hour snorkel near the Captain Cook Monument. Sea Paradise supplies masks, fins, flotation gear, reef-safe sunscreen, snacks, fruit, and drinks. Expect a powered catamaran, cultural commentary, and a maximum of 44 people.

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

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

Set sail from Kailua-Kona aboard a 50-foot catamaran with a friendly crew such as Captain Dan and Captain Jacques. Enjoy Kona coffee and pastries, snorkel for about an hour at Kealakekua Bay, then build a deli lunch before sailing home. Instruction, gear, flotation noodles, drinks, and reef guidance are included.

“Amazing snorkeling trip. Friendly and helpful crew, amazing boat and snorkeling gear and the fish and coral are incredible!”

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3.Deluxe Sail & Snorkel to the Captain Cook Monument

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

From Keauhou Bay, Sea Paradise takes you along the Kona coast to Red Hill’s underwater lava formations and the reef at Captain Cook Monument. You get breakfast, lunch, snacks, gear, reef-safe sunscreen, and instruction. Crew members such as Captain T-Roy and Fernando are praised for clear safety help, local stories, and friendly service.

“This was so much fun! Great crew. Very attentive . They are very invested in providing a great experience”

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4.Deluxe Sail & Snorkel to the Captain Cook Monument

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

Start at 8:15 a.m. from Keauhou Bay for a 4.5-hour catamaran sail along the Kona coast. Snorkel in Kealakekua Bay and near the Captain Cook Monument, with a possible third stop at Red Hill. Breakfast, lunch, gear, reef-safe sunscreen, drinks, and guided safety support are included.

“Very kind and welcoming. Helpful and considerate. Felt safe enough to fall asleep on the net on the front.”

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5.Waikoloa Signature Catamaran Sunset Sail

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

Board a 53-foot power catamaran from Anaehoomalu Bay for a relaxed 90-minute sunset sail along the Kohala-Kona coast. You’ll cruise barefoot, enjoy premium cocktails, beer, wine, snacks, and live commentary, then pause offshore for sunset and a possible green flash. The boat holds up to 49 people.

“This cruise is accessed by a tender boat right off the beach. You have to leave your shoes off, and step up a couple steps to board the tender. It was pretty easy. It is a little bit of a walk from the parking area at Lava Lava beach club, which was fine on the walk there....coming back after dark was more challenging, make sure your phone has a flashlight! The lighting is horrible at the beach club, even with our phone light it was tricky finding our way back safely.”

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6.Afternoon Sail & Snorkel to the Captain Cook Monument

★★★★★★★★★★5.0 · 246 reviews · 3 hours (approx.) · from $136

Join Sea Paradise at 2 p.m. for a three-hour trimaran sail from Keauhou Bay to Kealakekua Bay. Snorkel near the Captain Cook Monument with provided gear, flotation noodles, reef-safe sunscreen, snacks, and drinks. The crew offers instruction for beginners, shares Hawaiian history, and may spot spinner dolphins along the coast.

“We were well taken care of, and had an absolute blast hanging with the crew! Best marg in Kona. We booked last minute, for four people, and it was a breeze!”

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7.Kona Signature Catamaran Sunset Sail

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

Sail the Kona Coast aboard a spacious catamaran for about 90 minutes, with Captain Michael and crew members such as Caesar, John, or Kevin often helping on board. You get sunset views, possible dolphins or whales, light bites, a casual dinner, and a full bar with cocktails, beer, wine, soda, and juice.

“A great time with an excellent crew! Food and drinks were delicious and the music was on point. Highly recommend.”

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8.Kona Deluxe Catamaran Whale Watch

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

Set out from Honokohau Harbor aboard the Spirit of Aloha for a 90-minute Kona whale watch. The crew shares facts about humpback whales, serves drinks from a full bar, and points out sprays, tails, dolphins, and calves. Whale sightings are guaranteed with a free return trip, though the guarantee is not a cash refund.

“Fun, informative tour with a great captain and crew! We loved that the tour was smaller and being on the catamaran was a great experience. Saw dolphins and whales. Would recommend!”

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9.Kona Tradewind Catamaran Day Sail

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

Join Hawaii Nautical at Honokohau Small Boat Harbor for a 90-minute afternoon sail aboard Honi Olani, a 53-foot catamaran. You’ll cruise past Kailua-Kona and along the Kona coast with soft drinks, a full bar, shaded seating, restrooms, and a crew that may point out dolphins, flying fish, goats, reefs, and sunset colors.

“Perfect mid-afternoon no-frills cruise. Great opportunity to put in the middle of your vacation for a few hours of relaxing under sail. We saw a large pod of spinner dolphin, a bunch of goats along the coast, and thousands of flying fish. Great boat, with a great crew! No snorkeling, no dinner, just a relaxing cruise with snacks and drinks available.”

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10.Kona Luxury Catamaran Yacht Snorkel & Sail

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

Set out from Honokohau Harbor at 9 a.m. for a four-hour Kona Coast sail and snorkel aboard a high-end vessel limited to six people. Swim near Pawai Bay or Makalawena, use quality gear and prescription masks, then enjoy lunch, drinks, and shaded seating. Crews such as Cindy, Gretchen, John, Sean, and Liz have earned special praise.

“A fantastic tour. The boat really is luxury - superbly fitted out - and the crew were great. Not the cheapest tour we went on in Hawaii but definitely value for money.”

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

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

Set out from Keauhou Bay at 8:00 a.m. aboard Kini Kini, a traditional Hawaiian double-hull sailing canoe operated by Eka Canoe Adventures. You’ll cruise south along the Kona coast, stop at a selected snorkel cove for 50 to 60 minutes, and return with guided stories about Hawaii’s coastline, history, and culture. Gear, flotation devices, drinks, and snacks are included.

“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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12.Afternoon Tradewind Sail from Waikoloa

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

Set out at 1:45 pm from A-Bay in Waikoloa aboard the catamaran Spirit of Aloha for a 90-minute sail along the Kohala Coast. Enjoy juice, soda, and water while watching for dolphins and other sea life. Boarding is barefoot from the beach, so wear swimwear and footwear that can get wet.

“No wildlife seen, but was an awesome experience and got another ride out of it that we will take a day later. Fun guys to talk to! Thanks James, Josh, Jay, and Brandon!”

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13.Waikoloa Turtle Catamaran Snorkel Sail

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

Board Hawaii Nautical’s 2-hour catamaran at Anaeho'omalu Bay for a short sail, guided snorkeling, and a chance to see Hawaiian green turtles and reef fish. Sanitized gear, flotation equipment, snacks, shaded seating, restrooms, freshwater rinse, and a full premium bar are included. Beach boarding requires barefoot steps into seawater.

“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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