15 Best Maui Sailing Trips Worldwide

Catamaran Cruises, Cruises & Boat Tours, Dolphin & Whale Sails, Marina & Harbor Cruises, Maui, Maui Sailing Trips, Sailing, Tour Reviews, Tours, Whale Watching

Ma’alaea Harbor: Whale Watching Tour Aboard Power Catamaran

/ June 12, 2026

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

See Maui’s humpback whales from a double-deck power catamaran with onboard hydrophones, narration, and included drinks on a 2-hour ride.

Ma’alaea Harbor: Whale Watching Tour Aboard Power Catamaran

/ June 12, 2026

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

Maui humpback whales from a double-deck power catamaran with live narration, underwater hydrophones, and good non-alcoholic drinks.

★ 4.7

“Great fun! learned a lot from the captain and got to see the whales! Don’t skip on the drinks :)”

827 reviewsFrom $50by Quicksilver Charters

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Cruises & Boat Tours, Luxury Yacht Trips, Maui, Maui Sailing Trips, Sailing, Snorkel Sailing Trips, Tour Reviews, VIP

Maui: Molokini and Turtles Luxury Yacht Snorkel

/ July 28, 2026

3.Maui: Molokini and Turtles Luxury Yacht Snorkel

Luxury yacht snorkel in Maui with Molokini Crater and sea turtles, plus breakfast, BBQ lunch, and an open bar, all in about 5 hours.

★ 5.0

“Brilliant experience - tons of whales and superb snorkeling experience. The crew are all great at making you feel comfortable and taken care of”

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

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Catamaran Cruises, Cruises & Boat Tours, Evening Experiences, Maui, Maui Sailing Trips, Sailing, Sunset Sails, Tour Reviews, Tours

From Ma’alaea: ‘Alihilani Sunset Sail Catamaran Tour

/ August 6, 2026

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

2-hour Alihilani sunset catamaran from Ma’alaea with ice-cold drinks, hors d’oeuvres, wildlife spotting, and sail-powered Maui views.

★ 4.8

“Excellent tour. All the staff was so friendly. They were available all the time for serving or helping you with any query . Snacks and drinks were good . Trampoline sort of seating in front of cruise ship was cool. Captain Nicholas was funny and make sure it is not a boring sunset cruise. It…”

348 reviewsFrom $114by Sail Maui

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Maui, Maui Sailing Trips, Parasailing, Tour Reviews

Maui Parasailing Experience from Ka’anapali

/ August 10, 2026

5.Maui Parasailing Experience from Ka’anapali

UFO Parasail Maui from Ka’anapali: choose 800 or 1,200 ft, enjoy dry boat takeoff/landing, and spot Maui from above and near.

★ 5.0

“Amanda and James made it very easy for 4 elderly women. Beautiful scenery. The crew was very friendly and helpful.”

295 reviews1 hour (approx.)From $88.67by UFO Parasail Maui

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Cruises & Boat Tours, Lunch Experiences, Maui, Maui Sailing Trips, Snorkel Sailing Trips, Tour Reviews

Maui: Molokini Snorkel and Performance Sail with Lunch

/ August 19, 2026

6.Maui: Molokini Snorkel and Performance Sail with Lunch

A 5-hour Molokini snorkel and performance sail from Ma’alaea: fast catamaran, protected crater water, whale sightings, and a full lunch.

★ 4.8

“Awesome snorkel trip with a great crew! Boat wasn’t overcrowded and the food was good! Can’t ask for much more!”

224 reviews5 hoursFrom $200by Sail Maui

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Cruises & Boat Tours, Marina & Harbor Cruises, Maui, Maui Sailing Trips, Snorkel Sailing Trips, Tour Reviews

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

/ August 21, 2026

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

Catamaran snorkel from Mā’alaea to Molokini Crater with gear, reef-safe sunscreen, breakfast, buffet lunch, and possible whale sightings.

★ 5.0

“So great. We messed up reading the instructions and arrived close to departure and then had trouble finding where to go but they waited for us and we were so glad the did. The boat is beautiful and the ride over was even more beautiful. We saw whales both directions. The crew was great! The…”

214 reviews5 hours (approx.)From $200.00by Sail Maui

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1-Day Tours, Cruises & Boat Tours, Lunch Experiences, Maui, Maui Sailing Trips, Sailing, Snorkel Sailing Trips, Snorkeling, Tour Reviews

Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch

/ August 21, 2026

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

Sail West Maui on a luxury catamaran for Lanai snorkeling, humpback whale chances, and breakfast plus a full deli-style lunch with open bar.

★ 4.8

“Thsi was so much fun! Loved every bit of it. The workers were so great!”

210 reviewsFrom $200by Sail Maui

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1-Day Tours, Cruises & Boat Tours, Lunch Experiences, Maui, Maui Sailing Trips, Sailing, Snorkel Sailing Trips, Snorkeling, Tour Reviews

Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch

/ August 22, 2026

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

5-hour West Maui catamaran with flexible snorkeling stops, breakfast and deli-style lunch, reef-safe gear, and open bar. Whale season.

★ 4.8

“Captain Chase and his experienced crew ably took care of us. Jeff was especially helpful. Snorkeling was fabulous and the music playlist was a perfect fit to the day. Food was standard, and drinks were slightly less spirited than expected. Still, a wonderful time was had by all. Many thanks for the great sail and…”

210 reviewsFrom $200by Sail Maui

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Cruises & Boat Tours, Evening Experiences, Marina & Harbor Cruises, Maui, Maui Sailing Trips, Sunset Sails, Tour Reviews

Sunset Sail from Ma’alaea Harbor

/ August 22, 2026

10.Sunset Sail from Ma’alaea Harbor

2-hour sunset sail from Ma’alaea Harbor on the Ocean Spirit with pupus, non-alcoholic drinks, and BYOB, plus whale and dolphin chances.

★ 4.5

“The crew was so amazing. Having to serve in crazy wind was impressive but even more they did it with smiles and positive energy.”

207 reviewsFrom $151.00by Pacific Whale Foundation

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Catamaran Cruises, Cruises & Boat Tours, Dolphin & Whale Sails, Maui, Maui Sailing Trips, Sailing, Tour Reviews, Tours, Whale Watching

Whale Watching Tour on a Charming Hawaiian Catamaran From Maalaea

/ August 25, 2026

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

Whale watching on Maui from Maalaea aboard a Hawaiian-built catamaran, with hydrophones, snacks, drinks, and often dolphins.

★ 5.0

“The whole crew was very nice and very knowledgeable about whales. They were diligent about getting everyone location info in advance so they could show up on time in the right place. Definitely would use them again.”

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

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Cruises & Boat Tours, Drinking Tours, Evening Experiences, Maui, Maui Sailing Trips, Party & Music Cruises, Sunset Sails, Tour Reviews, VIP

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

/ September 5, 2026

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

Sail into Maui sunset from Ka’anapali on a luxury catamaran with open bar, pupus, and possible humpbacks in season.

★ 4.7

“Loved this boat trip, great crew, shout out to Captain Ian, Myles and Anna. Boarded the Teralani catamaran from the beach and had a great time sipping cocktails and watching the sun go down. We also saw whales and a dolphin swam alongside the boat. Would definitely recommend this trip. 5 stars.”

150 reviews2 hoursFrom $134by Teralani Sailing Adventures

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Cruises & Boat Tours, Dining Experiences, Dinner & BBQ Cruises, Dinner Experiences, Evening Experiences, Maui, Maui Sailing Trips, Sunset Sails, Tour Reviews, VIP

Maui: Ka’anapali Luxury Sunset Dinner Sail

/ September 13, 2026

13.Maui: Ka’anapali Luxury Sunset Dinner Sail

Luxury Ka'anapali sunset dinner sail on a catamaran with open bar, local buffet, and whale spotting off Maui’s West coast.

★ 4.8

“Amazing experience for my husband and I on our honeymoon. The crew was very friendly, knowledgeable, helpful, entertaining, and accommodating. The boat we went out on was brand new and in perfect condition. The huge bathrooms were amazing! Because of COVID there were fewer people on the boat than normal, which was really nice because…”

123 reviews2.5 hoursFrom $169by Teralani Sailing Adventures

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