Under sail · MAUI SAILING TOURS

The 4 Best Maui Sailing Tours

4 sailing trips  ·  seats from $114 each

Every harbour in Maui has a skipper selling seats. These 4 are the ones to choose, with prices and times laid out.

From Ma'alaea: 'Alihilani Sunset Sail Catamaran Tour - Three ways to enjoy the boat
Catamaran Sailing Trips, Catamaran Sailing Trips in the USA, Maui Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Sunset Sailing Cruises in the USA, Tour Reviews, Tours, USA Sailing Tours

From Ma’alaea: ‘Alihilani Sunset Sail Catamaran Tour

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

★★★★★★★★★★4.8 · 348 reviews · from $114Top of the fleet

Sail Maui’s Alihilani catamaran carries you from Maalaea Harbor into the Auau Channel for a two-hour sunset sail. Expect cold snacks, included drinks, open trampolines, covered seating, and an English-speaking crew. From December through March, keep watch for humpback whales. Check in at slip 72.

“This activity was fun & relaxing. I attended with my husband, my mom, and my 9 year old daughter. The staff was super friendly came around talking to everyone and made sure we had something to drink when our cups were close to empty. They don't really plan an exact time of being out there just until the sun goes down. Please note this is a catamaran and they ask you to take off your shoes before getting onto the boat (something I wasn't aware of). Wear something comfortable doesn't get even a little chilly maybe until the end of the activity but not much. Overall we had a good…”

Check sailing dates →Read the whole sail review

Maui: Molokini Snorkel and Performance Sail with Lunch - Leaving Ma’alaea Harbor with breakfast
Maui Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Sailing Tours with Lunch, Tour Reviews, USA Sailing Tours

Maui: Molokini Snorkel and Performance Sail with Lunch

2.Maui: Molokini Snorkel and Performance Sail with Lunch

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

Sail Maui takes you from Ma’alaea Harbor to Molokini on a fast catamaran with a small-group feel. You get continental breakfast, snorkel gear, reef-safe sunscreen, buffet lunch, and drinks. Snorkel for about 1.5 to 2 hours, then help at the helm or watch for whales from December through May. Captain Brandon, Captain Greg, Ben, and other crew members have earned strong praise for their friendly care.

“The people working there were amazing ! They really took care of us, a special hello to Ben”

Check sailing dates →Read the whole sail review

Molokini Snorkel and Performance Sail: Mā’alaea Harbor - Breakfast, coffee, and the first miles offshore
Maui Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Tour Reviews, USA Sailing Tours

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 $200Best loved

Start at 7:30 am from Mā’alaea Harbor aboard a Sail Maui catamaran bound for Molokini Crater. You’ll receive snorkel gear, flotation support, reef-safe sunscreen, breakfast, lunch, and drinks. Crew members such as Jeff, Brandon, Micah, and Captain Greg are praised for friendly help, while winter departures may add whale sightings and dolphins.

“This was a great experience. We saw at least 50 whales and had a magical experience snorkeling in the Molokini crater. The crew (AJ, Brandon, Jeff) were amazing and helped make sure that all of us were comfortable. Breakfast, lunch and coffee was provided, and we overall ended up having a very comfortable luxury adventure experience. I strongly recommend this for all travelers!”

Check sailing dates →Read the whole sail review

Maalaea: West Maui Snorkeling & Sailing Day Trip with Lunch - Breakfast, reef-safe sunscreen, and the first stretch of sailing
1-Day Tours, Maui Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in the USA, Sailing Tours, Sailing Tours with Lunch, Tour Reviews, USA Sailing Tours

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

Meet the crew at slip 72 in Maalaea Harbor for a five-hour Sail Maui catamaran trip toward Lanai. You’ll snorkel at reef sites chosen for the day’s conditions, enjoy breakfast and buffet lunch, and have beer, wine, cocktails, and soft drinks. Captains Patrick, Ron, and Chase are among the crew members named by past participants.

“Clean catamaran, good food & drinks, friendly crew who went out of their way to help. Saw a pod of dolphins which was an extra bonus! Captain tried to position the boat for the best view of them, super awesome! For the price I think it was money well spent.”

Check sailing dates →Read the whole sail review

Other ways to get on the water

Sunset Sailing CruisesCatamaran Sailing TripsSailing and Snorkeling TripsPrivate Sailing ChartersIsland Hopping Sailing TripsTall Ship and Schooner Sailing
Scroll to Top

Explore sailing

Pick a boat, a coast or a time of day.

Kinds of sail

Catamaran tripsTall shipsYacht chartersPrivate chartersLessons

Time of day

Golden-hour sailsDinner sailsParty sailsTwo-hour sailsFull-day sails

On board

Drinks on boardLunch at anchorSwim stopsSnorkel sails

Out at sea

Island hoppingWhales and dolphinsNile feluccasEvery sailing trip