MAUI

15 Maui Sailing Tours Worth Booking

17 sailing trips  ·  from $81 a head

The good maui sailing tours fill up weeks ahead and the small boats go first. Below: the 15 to book early, what each includes and how they differ.

From Ma'alaea: 'Alihilani Sunset Sail Catamaran Tour - Sailing the Auau Channel without a rushed schedule
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From Ma’alaea: ‘Alihilani Sunset Sail Catamaran Tour

1.From Ma’alaea: ‘Alihilani Sunset Sail Catamaran Tour

★★★★★★★★★★4.8 · 348 reviews · from $114Our pick

Sail Maui’s two-hour Alihilani sunset catamaran from Maalaea with ocean views, drinks, cold appetizers, music, and possible whale sightings.

“The crew, Patrick, Jeff, Malani and Kyrstin were great. They really went beyond to accommodate everyone. The experience was relaxing and the bottomless drinks were a nice bonus. Highly recommend!!”

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Maui: Molokini Snorkel and Performance Sail with Lunch - Leaving Ma’alaea Harbor with breakfast
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Maui: Molokini Snorkel and Performance Sail with Lunch

Molokini Snorkel and Performance Sail: Mā’alaea Harbor - Sailing across the channel toward Molokini
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Molokini Snorkel and Performance Sail: Mā’alaea Harbor

3.Molokini Snorkel and Performance Sail: Mā’alaea Harbor

★★★★★★★★★★5.0 · 214 reviews · 5 hours (approx.) · from $200Top rated

Review of Sail Maui’s Molokini snorkel sail from Mā’alaea Harbor, with food, drinks, whale sightings, group size, value, and booking tips.

“Great small group tour with captain Greg, Ben and Micah! Everyone was super personable and friendly. Happy to be on a smaller boat with a knowledgeable captain and wonderful crew! Breakfast, lunch and drinks!”

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Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch - Sailing the West Maui coast toward Lanai
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Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch

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

★★★★★★★★★★4.8 · 210 reviews · from $200

Review of Maui’s five-hour West Coast snorkel and sail to Lanai, with reef stops, whale watching, breakfast, lunch, and open bar.

“Our trip to Lanai was windy and choppy but that did not ruin the experience. The crew was so kind and friendly. The crews first priority was safety and that made me feel so comfortable on our trip. We had to find a calm spot to snorkel which took a while but the crew kept us informed and explained everything. The food was perfect and the drinks kept coming so I was very happy. One of my children got seasick (even though I gave her medicine before we got on) and the crew was so helpful and understanding. They are a wonderful crew and I would recommend this adventure for…”

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Sunset Sail from Ma'alaea Harbor - What Comes With the $151 Price
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Sunset Sail from Ma’alaea Harbor

5.Sunset Sail from Ma’alaea Harbor

★★★★★★★★★★4.5 · 207 reviews · from $151

Review of Maui’s two-hour sunset sail from Ma'alaea Harbor, with catamaran views, pupus, drinks, whale watching, costs, and practical tips.

“Like an absolute waking dream. STUNNING. Peaceful. Tranquil. Great pupus. WONDERDUL captain and crew. Cannot wait to return!!! MAHALO!!!”

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Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar - Boarding a luxury catamaran from the beach
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Maui: Ka’anapali Luxury Sunset Cocktail Sail with Open Bar

Maui: Ka'anapali Luxury Sunset Dinner Sail - A catamaran built for sunset views
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Maui: Ka’anapali Luxury Sunset Dinner Sail

7.Ka’anapali Luxury Sunset Dinner Sail

★★★★★★★★★★4.8 · 123 reviews · 2h 30m · from $169

Review of Maui’s Ka’anapali luxury sunset dinner sail, with catamaran views, open bar, local buffet, whale sightings, tips, and value advice.

“It was fun. Great staff. Great food. The only issue was knowing where to park. We barely made it on to the boat on time.”

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Maui: Snorkeling and Sailing Adventure with Buffet Lunch - Meeting the Gemini near Whalers Village
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Maui: Snorkeling and Sailing Adventure with Buffet Lunch

Maui: Ka'anapali Whale Watching Cruise on Luxury Sailboat - Watching North Pacific humpback whales near Maui
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Maui: Ka’anapali Whale Watching Cruise on Luxury Sailboat

9.Ka’anapali Whale Watching Cruise on Luxury Sailboat

★★★★★★★★★★4.8 · 89 reviews · from $108

Review of Maui’s Ka'anapali whale-watching cruise, with beach loading, live commentary, hydrophone, snacks, drinks, and value tips.

“Tylie and Julia were personable, fun, and very informational. Captain Matt made sure to get us in right in the path of the whales for a wonderful experience. We saw lots of whales and even got to experience males fighting over a female. Overall a wonderful experience and great crew. I would 100 percent recommend this experience with these wonderful people to anyone and can’t wait to do it again on our next trip back!!”

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Maui: 2 Hour Sunset Dinner Sail with Open Bar and Appetizers - Settling into Gemini’s cushioned catamaran
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Maui: 2 Hour Sunset Dinner Sail with Open Bar and Appetizers

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Maui: Deluxe Whale Watch Sail & Lunch from Ma`alaea Harbor

Maui: Ma'alaea Catamaran Sunset Sail with Appetizers - Setting Sail Along Maui’s Coast
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Maui: Ma’alaea Catamaran Sunset Sail with Appetizers

Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar - Boarding a luxury catamaran from the beach
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Maui: Ka’anapali Luxury Sunset Cocktail Sail with Open Bar

13.Ka’anapali Luxury Sunset Cocktail Sail with Open Bar

★★★★★★★★★★4.5 · 5 reviews · 2 hours (approx.) · from $141

Review of Maui’s Ka’anapali sunset cocktail sail, with open bar, appetizers, whale sightings, practical tips, pricing, and booking advice.

“Fantastic crew and cruise. Drinks and appetizers were delicious and free flowing. Had the opportunity to see a lot of whales including babies. A perfect way to end the day!”

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Lahaina: Private Sunset Sailing Trip & West Maui Mountains - Meeting the crew at Whalers Village
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Lahaina: Private Sunset Sailing Trip & West Maui Mountains

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

★★★★★★★★★★5.0 · 3 reviews

Review of a private three-hour Maui sunset sail from Lahaina, with West Maui views, appetizers, marine life, and practical booking tips.

“Captain Patrick and Phil were wonderful. Beautiful sunset sail and so nice to be just our family. Appreciated all the island knowledge and attention to detail. Thank you for making this a great experience for one of our last nights In Maui.”

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