The 15 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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8.Afternoon Sail & Snorkel to the Captain Cook Monument

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

Join Sea Paradise for a three-hour afternoon trimaran cruise from Keauhou Bay to Kealakekua Bay. You’ll snorkel near Captain Cook Monument, learn about Hawaiian culture and the bay, watch for dolphins, and use provided gear, snacks, drinks, and reef-safe sunscreen.

“Fantastic crew. Enjoyed the history about cove and island. The snorkeling was fantastic. The breaching baby whale was wild.”

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9.Kona Signature Catamaran Sunset Sail

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

Spend about 90 minutes sailing from Honokohau Harbor along the Kona Coast. Hawaii Nautical provides shaded and open-air seating, a restroom, premium drinks, snacks, and often a casual meal such as teriyaki chicken. Captains Michael and other crew members keep the trip relaxed and social.

“Very friendly crew who satisfied every need. Clean, comfortable boat. Some difficulty getting on and off the boat for older people. Kevin and Ceaser were so helpful and fun! Great personalities”

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10.Waikoloa Catamaran Snorkel Sail Including Lunch

★★★★★★★★★★4.5 · 105 reviews · 3 hours (approx.) · from $189

Spend about three hours aboard the Spirit of Aloha, sailing from Anaeho'omalu Bay along the Kohala Coast. You’ll receive sanitized snorkel gear, in-water guidance, lunch, snacks, and drinks from a full premium bar. The crew may spot dolphins, turtles, manta rays, or whales, but wildlife sightings are never guaranteed.

“Crew and boat were great! A great way to get on the water and get a chance to snorkel further out than our hotel beach.”

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11.Kona Deluxe Catamaran Whale Watch

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

Sail from Honokohau Harbor aboard the Spirit of Aloha for a 90-minute Kona whale watch. The crew, including captains and deckhands such as Kirk, Stan, John, and James, explains whale behavior while you scan the coast. Enjoy shaded seating, restrooms, tropical drinks, and a return voucher if no whales appear.

“We had a great time on this tour. We only had a short amount of time on this visit to the island as coming from a cruise ship. It's close to the cruise tender port so it was a quick Uber ride over. The boat tour was informative and relaxed. We saw many whales and had a great couple of hours on the water.”

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12.Kona Tradewind Catamaran Day Sail

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

Board Honi Olani at Honokohau Harbor for a 90-minute Kona coast sail with shaded seating, front nets, restrooms, soft drinks, and a full bar. Captains and crew such as Michael, Cindy, and Roy keep the mood easygoing, while dolphins, flying fish, and sunset views are possible but never guaranteed.

“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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13.Kona Luxury Catamaran Yacht Snorkel & Sail

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

Spend about four hours aboard a luxury catamaran from Honokohau Harbor, snorkeling near Pawai Bay or Makalawena, watching for dolphins and whales, and enjoying lunch with drinks. The group is limited to six, with private changing areas, fresh-water showers, restrooms, and prescription masks available.

“The staff was really nice and friendly, they made us feel very comfortable all the time and when we got to snorkel it was beautiful, I recommend this tour to families and couples.”

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

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

Join Eka Canoe Adventures at 8:00 a.m. for a 2.5-hour sail aboard Kini Kini, a traditional Hawaiian double-hull canoe. Cruise south from Keauhou Bay, snorkel for 50 to 60 minutes with a guide nearby, and hear stories about Kona’s coast on the ride home.

“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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15.Afternoon Tradewind Sail from Waikoloa

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

Spend 90 minutes sailing the Kohala Coast aboard Spirit of Aloha from Waikoloa. The crew, including James, Josh, Jay, and Brandon, serves juice, soda, and water while you watch for dolphins, whales, seabirds, and other marine life. Boarding at A-Bay involves barefoot steps through seawater.

“Great to get out on the water and see the island from afar. Enjoyed getting to know some people on the cruise as well.”

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