Category Sailing

Maui · SAILING

Top 15 Sailing Trips on Maui, Ranked

15 reviewed

Ma’alaea Harbor: Whale Watching Tour Aboard Power Catamaran

Ma'alaea Harbor: Whale Watching Tour Aboard Power Catamaran - Double-Deck Power Catamaran Seating That Works in Real Life

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

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

Sail from Ma'alaea Harbor for a 2-hour humpback whale watch on a double-deck catamaran with hydrophones and great sight lines.

“We took our daughter on a whale-watching excursion for her ninth birthday. She was thrilled to observe the whales jumping. She counted nearly 20 of them. The tour guide was extremely knowledgeable and provided us with a wealth of information about the whales and their migration. Sandy Palmer”

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Maui: Molokini and Turtles Luxury Yacht Snorkel

Maui: Molokini and Turtles Luxury Yacht Snorkel - Maui to Molokini: What Makes the Crater Snorkel Worth It

2.Molokini and Turtles Luxury Yacht Snorkel

★★★★★★★★★★5.0 · 477 reviews · 5 hours (approx.) · from $263Top rated

Luxury yacht snorkeling from Maui to Molokini and Turtle Town with sea turtles, meals, and open bar in a small group.

“What a wonderful experience! Was my daughter’s first time snorkeling and was the perfect trip. The crew was very friendly and kind and and weather was fantastic. Got some good snorkeling in as well as whale watching. Couldn’t have asked for a better trip”

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From Ma’alaea: ‘Alihilani Sunset Sail Catamaran Tour

From Ma'alaea: 'Alihilani Sunset Sail Catamaran Tour - The Alihilani Catamaran: Deck Space and Comfort That Actually Help

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

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

2-hour Alihilani sunset sail from Ma’alaea Harbor with ice-cold drinks, cold hors d’oeuvres, and a real shot at dolphins and whales.

“Despite choppy waters, the trip was lots of fun. Crew was awesome. Visitors are needed as activity wasn’t very busy as the area is still reeling from the Lahaina fire of August 2023. Maui visitors are warmly welcomed.”

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Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch

Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch - Snorkeling strategy: how you get better reef time on a changing day

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

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

A 5-hour luxury catamaran day from Maalaea for flexible West Maui snorkeling, possible humpback whales, and breakfast plus lunch with open bar.

“Incredible day! Beautiful boat and full service crew. Great food and drinks and plenty of it! The banana bread was fantastic. The crew did everything to make us comfortable and to make sure we had a great time. We had a lovely peaceful sail at the end of the day as well. This was money well spent!”

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Whale Watching Tour on a Charming Hawaiian Catamaran From Maalaea

Whale Watching Tour on a Charming Hawaiian Catamaran From Maalaea - What you can realistically see: humpbacks, calves, and breaches

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

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

Sail on Maui’s Hawaiian-built catamaran for humpback whale sightings, hydrophone whale songs, and included snacks and drinks from Maalaea.

“Excellent trip with lots of whales and a wonderful crew with good drinks and snacks and the weather was great and it was a perfect day to be out on the water.”

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Maui: Snorkeling and Sailing Adventure with Buffet Lunch

Maui: Snorkeling and Sailing Adventure with Buffet Lunch - Honolua Bay Snorkeling: What You’re Actually Chasing

6.Snorkeling and Sailing Adventure with Buffet Lunch

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

4-hour Maui snorkeling and sailing on the Gemini with Honolua Bay sea life, hot buffet lunch, open bar, and whale or dolphin chances.

“the trip was fun,it was are first time snorkeling it took us a couple of minutes to get it, but thanks to the crew instructions we got it down, if you are on the fence about it you will be in good hands with the genesis crew, my wife lovedit.”

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Turtles & Tacos Luxury Catamaran Snorkel

Turtles & Tacos Luxury Catamaran Snorkel - Turtle Snorkeling on Maui: How the Guaranteed Sightings Work in Real Life

7.Turtles & Tacos Luxury Catamaran Snorkel

★★★★★★★★★★4.5 · 103 reviews · 3 hours (approx.) · from $199

Maui luxury catamaran snorkel for sea turtles with tacos, margaritas, and beer included, plus optional pro photo packages.

“The Captain (Bre) and Crew were so great!!! So professional and accommodating. We had an amazing time!!! Thank you all!”

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Maui: Ka’anapali Whale Watching Cruise on Luxury Sailboat

Maui: Ka'anapali Whale Watching Cruise on Luxury Sailboat - The Luxury Catamaran Comfort: Space, Shade, and Netting Seats

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran - Getting to the Meeting Point and Finding the Boat Fast

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

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

Sunset on Maui aboard the Winona catamaran tiki bar. Open bar, Hawaiian snacks, and whale season sightings from Maalaea Bay.

“What an amazing experience sunset cruising with whales to entertain us. Hands down one of the best experiences while on Maui. The crew members were awesome, funny, entertaining and knowledgeable about the area. Highly recommend Winona and her crew for an evening of fun.”

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Luxury Catamaran Whale Watch

Luxury Catamaran Whale Watch - Getting On and Off: Maalaea Pier Steps and Restrooms

10.Luxury Catamaran Whale Watch

★★★★★★★★★★5.0 · 66 reviews · 2 hours (approx.) · from $119

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

“Beautiful boat and amazing service. We had a great day and the captain was determined to find whales - which he did!!!”

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Hawaiian Canoe Sailing Experience in Maui

Hawaiian Canoe Sailing Experience in Maui - Wildlife You May See Off Wailea (And Why It Matters)

11.Hawaiian Canoe Sailing Experience in Maui

★★★★★★★★★★4.5 · 59 reviews · 2 hours (approx.)

Private outrigger canoe sailing in Maui’s Wailea coast with snorkeling, sea turtles, and seasonal humpback whales.

“If you prefer a more low key outing to enjoy the waves and see lots of marine life, this is the one. The canoe is as advertised in the photo. Great for a single family, even with smaller kids. Ours were 6 and 3 and had a blast. Sage and Kira were knowledgeable, personable, and all around great hosts for this tour. And 2 hours felt like the perfect amount of time to explore and continue on with the day. Plus they gave us tips about where our next adventure should be! I'd recommend this to anyone who feels uncomfortable with the idea of a boat full of people, but…”

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Kaanapali: Sunset Dinner Catamaran Cruise With Drinks

Kaanapali: Sunset Dinner Catamaran Cruise With Drinks - Where to Meet on Kaanapali Beachwalk (2435 Kaanapali Pkwy)

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only) - Adults-only luxury: the vibe, the space, and the crew pace

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

★★★★★★★★★★5.0 · 43 reviews · 2 hours 30 minutes (approx.) · from $289

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

“The view was beautiful- note that you stay in a bay for the entire duration, but there is a lot to see and the view changes drastically as the sun goes down. The boat was clean and well maintained. The food was nice - not amazing, but nice. The best part was that they just brought everything to us. We sat comfortably and enjoyed the ride while the staff ran drinks and brought us our food, course by course. The captain (Bree) was funny and welcoming and the crew were friendly and constantly looking to help.”

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From Maalaea: Whale Watching Catamaran Cruise with Drinks

From Maalaea: Whale Watching Catamaran Cruise with Drinks - Maalaea Road meeting point and getting on the pier fast

14.From Maalaea: Whale Watching Catamaran Cruise with Drinks

★★★★★★★★★★4.7 · 26 reviews · 2 hours · from $69

2-hour Maalaea whale watching catamaran with hydrophones, marine-biologist talk, and drinks; 21+ get two adult beverages.

“The guide spoke without a microphone so we couldn’t hear much of what they were saying most of the time with the music playing in the background. They didn’t seem too interested to look for the whales. We were able to see a pod of whales in the distance but certainly much farther than expected. Kind of disappointed!”

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Maui: Ma’alaea Catamaran Sunset Sail with Appetizers

Maui: Ma'alaea Catamaran Sunset Sail with Appetizers - Where you check in (Lahaina) and where the boat departs (Ma’alaea)

15.Ma’alaea Catamaran Sunset Sail with Appetizers

★★★★★★★★★★4.7 · 16 reviews · 2 hours - 150 minutes · from $137

A 2-hour Ma’alaea sunset catamaran with whale-spotting potential, certified naturalists, and a full spread of Maui-style appetizers plus unlimited drinks.

“The sunset cruise was a perfect evening! The crew was very professional. The appetizers and beverages were flavorful. A professional photographer took photos during the evening. Good music and conversation among the guests. Highly recommend!”

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