Category Sailing

Big Island · SAILING

Top 15 Sailing Trips on the Big Island

16 reviewed

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

Big Island: Captain Cook Snorkel On A Power Catamaran With Lunch - Sailing out of Kona aboard a power catamaran that feels easy to enjoy

1.Captain Cook Snorkel On A Power Catamaran With Lunch

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

Snorkel in historic Kealakekua Bay from Kona on a comfy power catamaran with lunch, reef gear, and a real chance at dolphins and whales.

“It was a great experience. Everyone was so helpful and friendly. We really enjoyed it. We took our son on this trip for his birthday. He said it was one of the best birthday presents he had ever had. He was visiting the big island from Colorado.”

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

Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona - The first hour in Kailua-Kona: check-in, parking, and getting settled

Waikoloa Signature Catamaran Sunset Sail

Waikoloa Signature Catamaran Sunset Sail - The catamaran ride itself: 49 people, shaded seating, clean restrooms

3.Waikoloa Signature Catamaran Sunset Sail

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

Waikoloa Big Island sunset catamaran with premium bar, lava coast views, sea turtle chances, and a green-flash moment at Anaehoʻomalu Bay.

“Enjoyable experience. The crew was fabulous. My only complaint there was an overcast and we couldn't see the sunset”

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Kona Signature Catamaran Sunset Sail

Kona Signature Catamaran Sunset Sail - Price and value: why $109 can make sense here

4.Kona Signature Catamaran Sunset Sail

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

Kona Signature Catamaran Sunset Sail: a 90-minute Kona coastline cruise with open-air views, premium drinks, snacks, and wildlife spotting.

“Read email they send to tell you where to meet, coordinates are helpful. We met Captain Michael and crew: John and Caesar. They were kind and helpful especially without our sea legs. We sat and were served drinks and a surprise meal. We saw dolphins and a beautiful sunset. A memorable part of our trip.”

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

Kailua-Kona: Captain Cook Reef Catamaran Day Trip with Lunch - Sailing out of the Kona harbor: snacks, shade, and the first wildlife chances

Waikoloa Catamaran Snorkel Sail Including Lunch

Waikoloa Catamaran Snorkel Sail Including Lunch - Wildlife chances: dolphins, turtles, and why some days feel better

6.Waikoloa Catamaran Snorkel Sail Including Lunch

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

Waikoloa catamaran snorkel sail on the Big Island with dolphins or turtles chances, guided snorkeling, and a full premium bar lunch.

“The crew were amazing, the vessel was meticulous! We did not see any dolphins 😞 The snorkeling experience was great. Snacks, sandwiches and drinks were perfect.”

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Kona Catamaran Snorkel Sail with Lunch

Kona Catamaran Snorkel Sail with Lunch - The 10:00 am Start: How the 3 Hours Feel in Real Time

7.Kona Catamaran Snorkel Sail with Lunch

★★★★★★★★★★5.0 · 101 reviews · 3 hours (approx.) · from $169

Kona catamaran snorkel sail with lunch from Honokohau. Sanitized gear, big ocean views, and a full premium bar in about 3 hours.

“The caption (Micheal) and crew were amazing. Very knowledgable. And just all around great people. One of the best adventures we booked. We would definitely do this again if we return here.”

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Waikoloa: Catamaran Sunset Sail with Cocktails

Waikoloa: Catamaran Sunset Sail with Cocktails - The view package: Kohala Coast, Mauna Kea, Hualālai, and the Pacific horizon

Sunset Cocktail Cruise on our Sailing Catamaran

Sunset Cocktail Cruise on our Sailing Catamaran - Unlimited Drinks and Pupu Snacks: How the Bar and Food Actually Help

Kona Deluxe Catamaran Whale Watch

Kona Deluxe Catamaran Whale Watch - A 90-Minute Catamaran Cruise Where the Crew Does the Scanning

10.Kona Deluxe Catamaran Whale Watch

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

Kona Deluxe Catamaran Whale Watch from Honokohau: 1.5-hour cruise with a premium bar, humpback whales, and a free return.

“The best part was seeing whales. The crew was very good. The weather was great. Would recommend to anyone.”

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Late-Morning Whale Watch on our Power Catamaran

Late-Morning Whale Watch on our Power Catamaran - Kohala Coast + Sanctuary Waters: Why the run matters

11.Late-Morning Whale Watch on our Power Catamaran

★★★★★★★★★★4.5 · 54 reviews · 1 hour 30 minutes (approx.) · from $125

Late-morning Big Island whale watch on a stable power catamaran with marine naturalists, whale sounds via hydrophone, and included drinks.

“Saw 6 whales for over an hour. Awesome experience and the crew made it even better serving drinks and educating us on whales and Hawaii.”

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Sunset Cruise with the Whales on our Sailing Catamaran

Sunset Cruise with the Whales on our Sailing Catamaran - Check-In and the Anaeho‘omalu Tender Transfer (What You Need to Know)

12.Sunset Cruise with the Whales on our Sailing Catamaran

★★★★★★★★★★5.0 · 48 reviews · 2 hours (approx.) · from $165

Sunset whale watching on a sailing catamaran off Kohala Coast with open bar, snacks, naturalist talk, and hydrophone whale songs.

“Meeting great people. Crew very friendly & acomadating. Also celebrating our 61 wedding anniversary Beautiful sunset also saw several whales. Made it the best!”

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Kona Tradewind Catamaran Day Sail

Kona Tradewind Catamaran Day Sail - The Kailua-Kona Loop: What the Two Stops Feel Like

13.Kona Tradewind Catamaran Day Sail

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

Sail the Kona coast on the Honi Olani catamaran with premium drinks, big ocean views, and real odds of dolphins on a 1.5-hour cruise.

“We love our afternoon sail up the coast. Of course we would have loved more wind but Keith did the best he could do. We only had 7 passengers so it felt like a private sail.”

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Kona Luxury Catamaran Yacht Snorkel & Sail

Kona Luxury Catamaran Yacht Snorkel & Sail - Getting onboard at Honokohau Small Boat Harbor (9:00am start)

14.Kona Luxury Catamaran Yacht Snorkel & Sail

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

Small-group luxury catamaran snorkeling from Honokohau on the Big Island, with private showers, bento or picnic lunch, and responsible wildlife watching.

“We got to see spinner dolphins and snorkel at one spot. We were hoping to snorkel at one more location but that didn't happen which I was kind of bummed about but it was still a wonderful trip and the crew was so hospitable. The food display was sweet and the lunch was acceptable.”

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Waikoloa Catamaran Snorkel & Sail Adventure with Lunch

Waikoloa Catamaran Snorkel & Sail Adventure with Lunch - Setting sail from Anae‘omalu Bay and cruising Waikoloa’s Kohala Coast

15.Waikoloa Catamaran Snorkel & Sail Adventure with Lunch

★★★★★★★★★★4.8 · 39 reviews · 3 hours · from $189

Waikoloa catamaran snorkel and sail with lunch: green sea turtles, reef time, Mauna Kea views, and a premium bar for $189.

“We had 8 people ranging from age 4 to 73 - everyone had a fantastic experience. It was the highlight of our stay in Hawaii. The snorkeling was great and the whale watching was spectacular!!!”

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