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11 Best Sailing Tours In Hawaii

Hawaii’s best days out.

The 11 sailing tours travellers book most across Oahu and Maui, with what each one costs, how long it runs and the operator behind it.

11 Best Sailing Tours In Hawaii

Ma'alaea Harbor: Whale Watching Tour Aboard Power Catamaran - The Captain’s Whale Notes: What the Narration Helps You Spot
Cruises & Boat Tours, Maui, Sailing, Tour Reviews, Tours, Whale Watching, Whale Watching Tours

Ma’alaea Harbor: Whale Watching Tour Aboard Power Catamaran

1.Ma’alaea Harbor: Whale Watching Tour Aboard Power Catamaran

Hear humpback songs on a narrated 2-hour Maui catamaran cruise from Ma'alaea Harbor. Watch breaches, tail slaps, and more.

Most Popular 4.7

“Everything was great!! We seen whales! The sun was shining it was a good day. The captain was very friendly and knowledgeable about the whales. The staff were polite and friendly served drinks . We would highly recommend this whale tour!!!”

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Maui: Molokini and Turtles Luxury Yacht Snorkel - Molokini Crater snorkeling: clearer water, classic reef energy
Cruises & Boat Tours, Maui, Molokini & Turtle Town Snorkeling, Sailing, Snorkeling Tours, Tour Reviews, VIP

Maui: Molokini and Turtles Luxury Yacht Snorkel

2.Maui: Molokini and Turtles Luxury Yacht Snorkel

Luxury yacht snorkel from Maui to Molokini and Turtle Town, with sea turtles, breakfast, BBQ lunch, and open bar.

5.0

“Awesome boat and crew, but cancelled 2 days in a row due to bad weather. On third day we finally went but never went to Molokini crater or turtle town due to wind and water conditions. Snorkeling was below average in a protected cove along shore.”

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Oahu: Waikiki Sunset Catamaran Sail and Swim - How the boarding works at Pink Sails Waikiki (and how to avoid stress)
Cruises & Boat Tours, Evening Experiences, Honolulu, Sailing, Sunset & Dinner Cruises, Tour Reviews

Oahu: Waikiki Sunset Catamaran Sail and Swim

Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch - The catamaran ride along West Maui: comfort, scenery, and real weather
1-Day Tours, Cruises & Boat Tours, Lunch Experiences, Maui, Sailing, Snorkeling, Snorkeling Tours, Tour Reviews

Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch

4.Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch

Sail West Maui on a luxury catamaran with included breakfast, lunch, snorkel gear, and an open bar, with flexible reef stops.

4.8

“It was outstanding and worth every dollar. Especially the guides were great. They explained everything very well and gave insights into everything. From our perspective, it was the best sail trip you can book in Maui. Best regards, Mahalo, the Swiss. It could not be better 🤙”

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Whale Watching Tour on a Charming Hawaiian Catamaran From Maalaea - Finding the Winona at 233 Maalaea Rd (and getting oriented fast)
Cruises & Boat Tours, Maui, Sailing, Tour Reviews, Tours, Whale Watching, Whale Watching Tours

Whale Watching Tour on a Charming Hawaiian Catamaran From Maalaea

Turtles & Tacos Luxury Catamaran Snorkel - The Catamaran Setup: Shade, Hammocks, and Getting In
Cruises & Boat Tours, Maui, Sailing, Snorkeling Tours, Tour Reviews, VIP

Turtles & Tacos Luxury Catamaran Snorkel

7.Turtles & Tacos Luxury Catamaran Snorkel

Lux catamaran snorkeling in Maui with guaranteed honu, taco lunch and open bar, plus pro photos. 3 hours from Maalaea Harbor.

4.5

“This trip was the perfect day. Snorkeling with Turtles and eating delicious tacos after. We had a surprise appearance from a bunch of humpback whales in the distance. Very friendly and knowledgeable crew. The catamaran had stairs that lowered into the water. You didn’t have to climb a swim ladder.”

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Luxury Catamaran Whale Watch - Comfort and motion: decks, shaded cabin, restrooms, and the step onto the boat
Cruises & Boat Tours, Maui, Sailing, Tour Reviews, VIP, Whale Watching, Whale Watching Tours

Luxury Catamaran Whale Watch

9.Luxury Catamaran Whale Watch

Luxury catamaran whale watch from West Maui with marine naturalist, premium open bar, and hydrophone whale songs.

5.0

“Very friendly, knowledgeable accommodating crew!……………………………………………………………………………………………………………………………………..”

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Hawaiian Canoe Sailing Experience in Maui - Snorkeling in Maui’s Secret Spots: What You Can Actually See
Canoes & Kayaks, Cruises & Boat Tours, Maui, Sailing, Tour Reviews

Hawaiian Canoe Sailing Experience in Maui

11.Hawaiian Canoe Sailing Experience in Maui

Sail Maui’s Wailea coast on a private outrigger canoe with snorkeling gear included, chasing sea turtles and possible humpback whales.

4.5

“Amazing experience. Super fun on a handmade Hawaiian Canoe. Complete with snorkeling gear, crystal clear waters made for an awesome adventure! Thank you!”

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