Under sail · BIG ISLAND SAILING TOURS

Sailing in Big Island: the 5 Best Trips

5 sailing trips  ·  seats from $137 each

Short on days in Big Island? Give one of them to the water. Below, 5 sailing trips that earn it.

Afternoon Sail & Snorkel to the Captain Cook Monument - Entering Kealakekua Bay with respect
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Afternoon Sail & Snorkel to the Captain Cook Monument

1.Afternoon Sail & Snorkel to the Captain Cook Monument

★★★★★★★★★★5.0 · 722 reviews · 3 hours (approx.) · from $136Top of the fleet

From Keauhou Bay, you’ll cruise along Kona’s lava-lined coast to Kealakekua Bay, where a guide leads a one-hour snorkel near the Captain Cook Monument. Sea Paradise supplies masks, fins, flotation noodles, reef-safe sunscreen, snacks, and drinks. Expect a 44-person maximum, afternoon departure, and a crew that shares local history and ocean safety.

“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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Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure - Breakfast With Kona Coffee and Coast Views
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Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

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

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

Sail Kona’s coast aboard a 50-foot catamaran with a crew that may include Captains Dan, Jacques, or Nick. Enjoy Kona coffee and pastries, watch for dolphins and seasonal whales, then snorkel for about an hour at Kealakekua Bay. A water staircase, flotation noodles, lunch, and non-alcoholic drinks are included.

“My spouse and I booked this activity for our first trip to Hawaii's Big Island. We had a great time and the crew is awesome! It was the perfect size group (around 24 folks) and there is a lot to do and see on Big Island, so the half day worked great.”

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Deluxe Sail & Snorkel to the Captain Cook Monument - Kealakekua Bay Marine Preserve, the main event
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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

Set out from Keauhou Bay at 8:15 a.m. aboard Sea Paradise’s catamaran for a 4.5-hour sail, breakfast, lunch, and two snorkel sessions. Swim near Captain Cook Monument and Red Hill’s lava formations with gear, flotation noodles, reef-safe sunscreen, and fish charts supplied. Crew members such as Captain T-Roy and Fernando may share local history along the way.

“Wonderful crew! Each one provided great service and support. We had one of our group who was snorkeling for the first time, and the crew watched over her and made her feel safe and comfortable. The snorkeling was top notch!”

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Deluxe Sail & Snorkel to the Captain Cook Monument - Kealakekua Bay Marine Preserve, the main event
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

Meet Sea Paradise at Keauhou Bay at 8:15 am for a 4.5-hour catamaran trip along the Kona coast. You’ll snorkel near the Captain Cook Monument and, weather permitting, at Red Hill, with breakfast, lunch, drinks, reef-safe sunscreen, gear, and attentive crew support included. The boat returns to Keauhou Bay.

“This was a great experience! Definitely recommend! The crew was great, very kind and patient with beginners! I will definitely book again!!”

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Waikoloa Signature Catamaran Sunset Sail - Drinks, Snacks, and the Onboard Setup
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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

Sail from Anaehoʻomalu Bay on a 53-foot catamaran with up to 49 people. Enjoy Pacific sunset views, live commentary, premium drinks, snacks, shaded seating, and a chance to spot whales, turtles, or the green flash. The barefoot boarding process and occasional rough water are worth planning for.

“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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Other ways to get on the water

Sunset Sailing CruisesCatamaran Sailing TripsSailing and Snorkeling TripsPrivate Sailing ChartersIsland Hopping Sailing TripsTall Ship and Schooner Sailing
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