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15 Best Sailing Tours In Maui

Maui’s best days out.

The 15 best sailing tours on Maui right now — what each day actually involves, who runs it, how long it takes and what you will pay.

15 Best Sailing Tours In Maui

Ma'alaea Harbor: Whale Watching Tour Aboard Power Catamaran - Double-deck layout and comfort that actually helps your whale spotting
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

A narrated 2-hour humpback whale cruise from Ma’alaea Harbor on a double-deck catamaran, with underwater hydrophones to hear whale songs.

Most Popular★ 4.7

“Captain Kiwi was very entertaining. We saw whales in several different locations leaving on the first boat departing in the morning. The service and crew were great. This was a nice value when you consider the costs of other whale watching options. We had good time!”

827 reviewsFrom $50by Quicksilver Charters

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Maui: Molokini and Turtles Luxury Yacht Snorkel - The luxury yacht details that actually matter on snorkel day
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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Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch - The boat and the vibe: luxury catamaran, but practical
1-Day Tours, Cruises & Boat Tours, Lunch Experiences, Maui, Sailing, Snorkeling, Snorkeling Tours, Sunset Sails & Sailing, Tour Reviews

Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch

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

5-hour West Maui catamaran trip from Maalaea: snorkel Lanai reefs, see turtles and humpbacks, plus breakfast, lunch, and open bar.

★ 4.8

“The guys on the sail were great--we couldn't head to Lanai b/c of winds and choppiness, but they took us to another spot, which was good snorkeling too. The sail back, going with the wind and waves current was relaxing and peaceful--”

210 reviewsFrom $200by Sail Maui

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Whale Watching Tour on a Charming Hawaiian Catamaran From Maalaea - How the 2.5-hour tour unfolds on the water
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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Turtles & Tacos Luxury Catamaran Snorkel - Your Snorkel Setup: Gear, Reef-Safe Sunscreen, and Easy Entry
Cruises & Boat Tours, Maui, Sailing, Snorkeling Tours, Tour Reviews, VIP

Turtles & Tacos Luxury Catamaran Snorkel

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6.Turtles & Tacos Luxury Catamaran Snorkel

Maui luxury catamaran snorkel with guaranteed honu sightings, taco lunch, and an open bar. 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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Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran - Where You’ll Start in Maui and How the Timing Works
Cruises & Boat Tours, Drinking Tours, Evening Experiences, Maui, Sailing, Sunset Sails & Sailing, Tour Reviews

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

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8.Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

2-hour Maui sunset cruise on a Hawaiian-built catamaran with tiki bar snacks, open bar, and winter whale watching in season.

★ 4.5

“The crew were super attentive, knowledgeable and kind. The tour was incredibly beautiful, fun, and whale-y amazing! The drinks were also plentiful and delicious. I’d do this tour over and over again. Thank you so much guys, much appreciated!”

87 reviews2 hours (approx.)From $119.00by Makena Coast Charters

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Luxury Catamaran Whale Watch - Premium open bar and snacks: the value angle you’ll care about
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 a marine naturalist, hydrophone for real-time whalesong, and an onboard open bar.

★ 5.0

“The crew (Ryan, Logan and Johanna) were organized and friendly. We saw a lot of whales and they moved the catamaran smoothly through the waters. The boat was clean and comfortable with room to move and follow the whales.”

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

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Hawaiian Canoe Sailing Experience in Maui - Sailing the Wailea Coast: Wildlife You Can Watch at Your Own Pace
Canoes & Kayaks, Cruises & Boat Tours, Maui, Sailing, Sunset Sails & Sailing, Tour Reviews

Hawaiian Canoe Sailing Experience in Maui

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10.Hawaiian Canoe Sailing Experience in Maui

Private outrigger canoe sailing in Wailea with snorkeling gear, sea turtles, sting rays, and possible humpback whales in a small group.

★ 4.5

“We seen a turtle and octopus. Sage was very knowledgeable about Maui and shared many stories! This was a great trip and would highly recommend this!”

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

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Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only) - Adults-only catamaran: the vibe you came for
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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12.Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Maui adults-only sunset catamaran dinner cruise from Maalaea Harbor with a plated five-course meal, top-shelf open bar, and photo service.

★ 5.0

“We are from Illinois and recently traveled to Hawaii, seeking once-in-a-lifetime experiences. This excursion was perfect, featuring a one-and-a-half-year old catamaran ride, a fantastic crew, an excellent meal, and a stunning sunset. It was an incredible experience!”

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 - Marine biologist talks and hydrophones: learning that makes the whales easier to spot
Cruises & Boat Tours, Maui, Sailing, Tour Reviews, Whale Watching, Whale Watching Tours

From Maalaea: Whale Watching Catamaran Cruise with Drinks

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Lahaina: Private Sunset Sailing Trip & West Maui Mountains - The Plan: 3 Hours From Whalers Village to Past Sunset
Cruises & Boat Tours, Evening Experiences, Maui, Private, Sailing, Sunset Sails & Sailing, Tour Reviews

Lahaina: Private Sunset Sailing Trip & West Maui Mountains

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15.Lahaina: Private Sunset Sailing Trip & West Maui Mountains

Private Lahaina sunset sailing with West Maui Mountain views, a fruit-and-cheese platter, and marine-life spotting on a 3-hour yacht cruise.

★ 5.0

“We had the most amazing time on our private sail with Captain Patrick and Matthew! The boat was pristine and they were an excellent and fun crew. This was the highlight of our time on Maui. Highly recommend!”

3 reviewsFrom $1,936by Kainani Sails

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