Category Maui Sailing Tours

Maui · MAUI SAILING TOURS

The 15 Best Maui Sailing Tours

22 reviewed

Ma’alaea Harbor: Whale Watching Tour Aboard Power Catamaran

Ma'alaea Harbor: Whale Watching Tour Aboard Power Catamaran - Cruising Ma’alaea Bay: what you’re actually looking for in 2 hours

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

★★★★★★★★★★4.6 · 979 reviews · 2 hours · from $49Our pick

Ma'alaea Harbor whale watching on a double-deck power catamaran, with hydrophones and humpback songs, plus comfy seating for 2 hours.

“boat, crew and facilities on board were excellent. exactly what's needed for 2 hours. Captain Kiwi was engaging and knowledgeable. speaking with other guests they said compared to other operators they had used this was excellent - I wouldn't argue.”

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From Ma’alaea: ‘Alihilani Sunset Sail Catamaran Tour

From Ma'alaea: 'Alihilani Sunset Sail Catamaran Tour - Boarding Alihilani: deck layout, shoe rules, and where to sit

Maui: Molokini Snorkel and Performance Sail with Lunch

Maui: Molokini Snorkel and Performance Sail with Lunch - Breakfast on the sail out of Maalaea Bay, plus whale-season odds

3.Molokini Snorkel and Performance Sail with Lunch

★★★★★★★★★★4.8 · 224 reviews · 5 hours · from $200

Molokini snorkel and performance sail from Ma'alaea: small-group catamaran, whale season sightings, breakfast, and a buffet lunch.

“The crew was amazing, they made our experience top notch. We had a beautiful day on the ocean and saw a ton of fish. would definately do this again.”

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Molokini Snorkel and Performance Sail: Mā’alaea Harbor

Molokini Snorkel and Performance Sail: Mā’alaea Harbor - The catamaran ride from Mā’alaea Harbor feels like part of the tour

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

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

Catamaran from Maalaea to Molokini for clear snorkeling, plus breakfast, lunch, and beer or wine included. 5-hour morning sail.

“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

Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch - Flexible snorkeling spots: why the plan is built for real ocean conditions

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

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

Luxury catamaran day from Maalaea to Lanai with flexible snorkeling, whales in season, breakfast and deli lunch, plus an 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

Sunset Sail from Ma'alaea Harbor - What You’re Paying $151 For, and What Feels Like Value

6.Sunset Sail from Ma’alaea Harbor

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

Maui sunset sail from Maalaea Harbor on the Ocean Spirit, with pupus, unlimited non-alcoholic drinks, and BYOB options.

“Beautiful night for a sunset cruise. Great cocktails! The captain & staff were super friendly. We didn’t see any whales but it was end is season for them so we knew that may be the case. We got amazing sunset pictures!”

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Whale Watching Tour on a Charming Hawaiian Catamaran From Maalaea

Whale Watching Tour on a Charming Hawaiian Catamaran From Maalaea - Underwater hydrophones: the moment most people remember

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

★★★★★★★★★★5.0 · 194 reviews · 2 hours 30 minutes (approx.) · from $85

See humpback whales on Maui’s catamaran Winona from Maalaea, with whale-song hydrophones, snacks and drinks, and a close-to-the-action feel.

“The whale watching trip was amazing! We were able to see several whales including a breaching one Captain Sam and his crew did a fantastic job!! I would definitely recommend this tour!!”

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Maui: Ka’anapali Luxury Sunset Cocktail Sail with Open Bar

Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar - The Boarding Flow: Check-In, Beach Loading, and Why It Changes Your Packing Plan

Maui: Ka’anapali Luxury Sunset Dinner Sail

Maui: Ka'anapali Luxury Sunset Dinner Sail - 150 Minutes of Sailing Time That Actually Feels Like a Dinner Event

9.Ka’anapali Luxury Sunset Dinner Sail

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

Ka'anapali luxury catamaran sunset dinner with open bar, chef-inspired buffet, and whale-spotting views along Maui's west coast.

“Our family went on the Teralani 5 sunset dinner cruise on May 21st. We had an excellent time with Captain Patrick, AJ, Isaiah, and the crew. Good dinner and drinks - highly recommend this in Maui!”

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Maui: Coast of Ka’anapali Beach Sunset Dinner Sail

Maui: Coast of Ka'anapali Beach Sunset Dinner Sail - The 2-Hour Itinerary: Kaanapali Out, Molokai-In, Back Again

10.Coast of Ka’anapali Beach Sunset Dinner Sail

★★★★★★★★★★5.0 · 121 reviews · 2 hours (approx.) · from $158

Sail Ka'anapali at sunset with an included dinner buffet and open bar on a catamaran, with possible whale sightings and Molokai views.

“I had relatively low expectations heading into it other than seeing a pretty sunset but I was blown away by how good the experience was. The boat wasn't crowded, The food was good, the drinks were very good, the playlist was on point, and Kayla and Drew both provided exceptional service. I would definitely recommend this cruise to anyone looking for a sunset sail”

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Maui: Snorkeling and Sailing Adventure with Buffet Lunch

Maui: Snorkeling and Sailing Adventure with Buffet Lunch - Finding the Gemini at Westin Maui and Whalers Village

11.Snorkeling and Sailing Adventure with Buffet Lunch

★★★★★★★★★★4.8 · 115 reviews · from $172

Snorkel Honolua Bay on Gemini, see turtles, then enjoy a hot buffet lunch and open bar on Maui’s west coast.

“The crew was so organized and made this whole operation run very smoothly! The open bar and lunch alone makes the price well worth it. The crew checked in to see what drinks we needed refills on. Talk about full service! We got to see whales during the ride, which the staff made a fun and informative experience! Aside from the amazing crew, the snorkeling was fantastic. My husband and I saw a reef shark, got to see at least 3 sea turtles, and so many beautiful fish. We would do this all over again. The Gemini is a one-boat operation, which impressed us even more. Definitely recommend this experience!Read…”

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Turtles & Tacos Luxury Catamaran Snorkel

Turtles & Tacos Luxury Catamaran Snorkel - Snorkeling for honu sea turtles, with included gear and an easy water entry

Maui: Ka’anapali Whale Watching Cruise on Luxury Sailboat

Maui: Ka'anapali Whale Watching Cruise on Luxury Sailboat - A Luxury Catamaran That Feels Big Enough for Everyone

13.Ka’anapali Whale Watching Cruise on Luxury Sailboat

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

Luxury Ka'anapali whale watch by catamaran with naturalist, hydrophone whale songs, snacks, open bar, and free return if no whales.

“We had a great time whale watching! The crew was knowledgeable and we saw lots of whales. The boat was comfortable with easy access and there were snacks provided. I would recommend this whale tour.”

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Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran - Your 4:30 pm start from Maalaea, what the timing does for you

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

★★★★★★★★★★4.5 · 87 reviews · 2 hours (approx.) · from $119

Maui sunset sailing on the Winona tiki catamaran with open bar snacks and wildlife spotting in season, about 2 hours from Maalaea.

“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!”

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West Maui Snorkel & Sail

West Maui Snorkel & Sail - Snorkeling Near West Maui: Turtles, Fish, and Reef Conservation

15.West Maui Snorkel & Sail

★★★★★★★★★★5.0 · 82 reviews · 5 hours (approx.) · from $206

West Maui Snorkel & Sail from Lahaina with reef-safe sunscreen, sea turtles, flexible snorkel stops, meals, and open bar.

“The crew was very accomodating and helpful. Good food. Small friendly group. This was everything we wanted it to be!!”

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