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15 Best Sailing Tours In Hawaii

Hawaii’s best days out.

The 15 sailing tours travellers book most across Oahu and Maui, with what each one costs, how long it runs and the operator behind it.

15 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

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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

“Everyone in our crew was absolutely friendly and kind, and very knowledgeable! We saw so many whales, which was unprecedented for this time of year, so, even the crew was excited! They made sure we got to see whales from all the angles, and it was just a great trip all around! Thank you so…”

827 reviewsFrom $50by Quicksilver Charters

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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

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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

“If you want an experience where the staff welcomes you and takes care of you like family, in an uncrowded relaxed and atmosphere, this is your luxury yacht. The captain and crew took time to slow the boat to enjoy a mama whale and her calf not 100 yards from the boat and did they…”

477 reviews5 hours (approx.)From $263.00by Pride of Maui

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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

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3.Oahu: Waikiki Sunset Catamaran Sail and Swim

Watch Diamond Head glow on a 2-hour Waikiki sunset catamaran, with time to swim and a standout crew for about $49.

★ 4.6

“The catamaran cruise was excellent!!! Pink Sails was very organized and knowledgeable with what they were doing. We felt safe on the boat. They were saving drinks on the boat. I don’t remember them serving food. The weather was perfect when we went. We were able to swim out too because the waves weren’t that…”

351 reviewsFrom $49by Pink Sails Waikiki

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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

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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

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5.Whale Watching Tour on a Charming Hawaiian Catamaran From Maalaea

Whale-watch from Maui’s Hawaiian-built catamaran Winona in Maalaea with snacks, drinks, and underwater hydrophones for humpback songs.

★ 5.0

“There is no bad whale watching on Maui. There are better than this, but these people are new to the business and still finding their way. They do have respect for the whales and knowledge but are still figuring out how to communicate it smoothly. The spotter would say, "There's a whale," but forget to…”

194 reviews2 hours 30 minutes (approx.)From $85.00by Makena Coast Charters

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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

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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.”

103 reviews3 hours (approx.)From $199.00by Alii Nui Sailing Charters

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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

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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!……………………………………………………………………………………………………………………………………..”

66 reviews2 hours (approx.)From $119.00by Alii Nui Sailing Charters

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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

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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!”

59 reviews2 hours (approx.)by Hawaiian Sailing Canoe Adventures

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Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only) - The Open Bar Reality: What You’re Really Buying
Cruises & Boat Tours, Dining Experiences, Dinner Experiences, Evening Experiences, Maui, Sailing, Sunset & Dinner Cruises, Tour Reviews, VIP

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

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13.Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Adults-only Maui sunset dinner cruise on a luxury catamaran with a top-shelf open bar, five-course plated meal, and photo option.

★ 5.0

“Very swanky experience. Great food, great crew, excellent food and drinks. Onboard photographer (extra fee) took some nice photos of us. The boat was pristine. I would do it again if I return to Maui!”

43 reviews2 hours 30 minutes (approx.)From $289.00by Alii Nui Sailing Charters

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From Maalaea: Whale Watching Catamaran Cruise with Drinks - Hydrophones and the Marine Biologist Talk: What You’ll Learn Beyond Sightings
Cruises & Boat Tours, Maui, Sailing, Tour Reviews, Whale Watching, Whale Watching Tours

From Maalaea: Whale Watching Catamaran Cruise with Drinks

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14.From Maalaea: Whale Watching Catamaran Cruise with Drinks

See humpback whales off Maalaea on a small catamaran with ice-cold drinks, a marine biologist talk, and hydrophones to hear whale songs.

★ 4.7

“The crew was great, friendly and helpful. We got free fruit, chips and soft drinks on the boat. The boat was clean and they were available at the restrooms. The trip was flawless and even though it was the very end of the season, we did encounter whales! The crew knew what they were doing…”

21 reviewsFrom $69by Makena Coast Charters

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Maui: Ma'alaea Catamaran Sunset Sail with Appetizers - The onboard layout: open deck, trampoline, and covered seating
Cruises & Boat Tours, Evening Experiences, Maui, Sailing, Sunset & Dinner Cruises, Tour Reviews

Maui: Ma’alaea Catamaran Sunset Sail with Appetizers

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More Sailing Tours In Hawaii

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