Maui

15 Best Maui Sailing & Catamaran Tours

Sailing is Maui showing off, and these are the catamaran trips I’d pick for snorkeling, whales, or plain wind in the sails. Several load right off the sand at Kaanapali Beach; you wade in, climb the ladder, and go. Afternoon departures catch true trade-wind sailing instead of motoring.

1.Ma’alaea Harbor: Whale Watching Catamaran Cruise

On a journey like no other, discover the ocean's secrets with Ma'alaea Harbor's Whale Watching Catamaran Cruise.

Most Popular★ 4.7

“Everything was great!! We seen whales! The sun was shining it was a good day. The captain was very friendly and knowledgeable about the whales. The staff were polite and friendly served drinks . We would highly recommend this whale tour!!!”

Check Availability →Read my full review →

2.Maui Parasailing Experience From Kaanapali

Witness the captivating aerial vistas of Maui's stunning landscape from the thrill of parasailing over the pristine Ka'anapali Beach.

★ 5.0

“Parasailing in Maui was thrilling and an unforgettable experience! The crew were friendly and incredibly helpful. This was our first time parasailing and the team made it smooth and very safe! Would definitely look at booking again!”

Check Availability →Read my full review →

3.Maui: Molokini Snorkel and Performance Sail With Lunch

Discover the ultimate adventure in Maui! Snorkel at Molokini, sail like a pro, and indulge in a delicious lunch. Click now for an unforgettable experience!

★ 4.8

“Captain Brandon and his crew were great. Super friendly, helpful and knowledgeable. Many times they detoured the boat so we could see whales, an amazing extra for our tour to Molokini. The snorkel spot in the crater was great and we got there at a…”

Check Availability →Read my full review →

4.Molokini Snorkel and Performance Sail From Maalaea Harbor

Lose yourself in the vibrant underwater world of Molokini Crater during a thrilling snorkel and sail adventure from Maalaea Harbor, where more surprises await.

★ 5.0

“Absolutely marvelous. Jeff, Brandon, Micah, and Lucas were exceptional with leading, assisting, and guiding us on an incredible excursion to Molokini Crater. We were graced by a mama humpback, her baby, and a pod of dolphins on the way. For an hour, they breached, swam…”

Check Availability →Read my full review →

6.Sunset Sail From Maalaea Harbor

Experience the magic of a sunset sail from Maalaea Harbor. Set sail on the shimmering waters and witness breathtaking views as the sun dips below the horizon.

★ 4.5

“We really enjoyed our sunset sail. Our all female crew were fun and hard working (I had no idea of the physical exertion required in hoisting the sail). The food was really good and my beer was cold. But the real attraction was nature itself.…”

Check Availability →Read my full review →

7.From Maalaea Harbor: Whale Watching Tours Aboard Winona Catamaran

Witness the enchanting songs of whales and the breathtaking views of Maui's coastline aboard the renowned Winona Catamaran, a tour that promises an unforgettable adventure.

★ 5.0

“Great experience. Saw over ten whales, both mothers with babies and males. We saw them all breaching and diving.”

Check Availability →Read my full review →

8.Maui: Snorkeling and Sailing Adventure With Buffet Lunch

Embark on an unforgettable Maui snorkeling and sailing adventure! Immerse yourself in the vibrant marine world, indulge in a delicious buffet lunch, and create lifelong memories.

“Amazing and loads of fun. Great music , informative of the reef and able to relax and see turtles , whales, dolphins , and our captain was great! She made sure to turn around and look for the whales , pause and patiently await their…”

Check Availability →Read my full review →

9.Turtles & Tacos Luxury Catamaran Snorkel

Adventure awaits on the Turtles & Tacos Luxury Catamaran Snorkel, where vibrant marine life and gourmet tacos promise an unforgettable experience—discover what surprises lie beneath the waves.

★ 4.5

“The crew is very professional and friendly, and the food and beverage service is top notch. We didn’t see any turtles that day, but the trip and snorkeling was still awesome!”

Check Availability →Read my full review →

10.Midday Sail With the Whales Maalaea

Experience the thrill of sailing with majestic whales in Maalaea. Join us for a midday adventure on the open seas. Book now!

★ 5.0

“The crew was fun and friendly. We had a great time. It was the perfect ending to our Maui trip. It was a relaxing and beautiful evening.”

Check Availability →Read my full review →

11.Maui: Sunset Dinner Sail in Ka’anapali

Experience the ultimate romantic evening on a sunset dinner sail in Maui's stunning Ka'anapali. Indulge in delectable cuisine while watching the sun melt into the horizon.

★ 4.6

“It was absolutely fantastic! The sunset was beautiful. We did not see any whales breach but we got to see some whales. The meal was great Good music and good appetizers”

Check Availability →Read my full review →

12.Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

Just imagine setting sail on a charming Hawaiian catamaran, sipping complimentary drinks as the sun dips below the horizon, creating a breathtaking display.

★ 4.5

“I was offended at being booed loudly for getting a nonalcoholic drink! I’ve been sober a long time and can’t imagine I’m the first adult non drinker they’ve had on the cruise. If I was newly sober that would’ve gone much differently and I would’ve…”

Check Availability →Read my full review →

13.West Maui Snorkel & Sail From Maalaea Harbor

Captivating marine life, breathtaking vistas, and a chance to immerse yourself in the vibrant coral reefs of West Maui await you on this unforgettable snorkel and sail adventure.

★ 5.0

“They took us out despite 15 people canceling last minute. We felt like we had rented a charter. Boat was beautiful and the staff was excellent. Even saw some turtles.”

Check Availability →Read my full review →

14.Alihilani Sunset Sail From Maalaea Harbor

Glide across Maui's waters aboard the Alihilani catamaran, soaking up stunning coastal vistas and the chance to spot majestic humpback whales during the enchanting sunset sail.

★ 5.0

“My family and I had a great time! The staff was very friendly and helpful. We caught a beautiful sunset along with some snacks and drinks.”

Check Availability →Read my full review →

15.Alii Nui Makani Cocktail Sunset Sail

Set sail on the Alii Nui Makani Cocktail Sunset Sail and be swept away by a mesmerizing experience that will leave you craving for more.

★ 4.5

“Beautiful boat and amazing area to be out in. The crew were super nice and friendly continuously making sure youre taken care of and having a good time. Loved they offered professional photos as well.”

Check Availability →Read my full review →