Whale Watching: Maui's Majestic Marine Adventure
4.7
14 Ratings
Wailuku

Embark on a thrilling Maalaea whale watching cruise, witness majestic humpbacks, and enjoy Maui’s stunning coastline. Book your unforgettable adventure today.

Duration: 2 hours, 30 minutes
Cancellation: 24 hours
Highlights
  • 223 Maalaea Rd - Step aboard the delightful Hawaiian Catamaran “Winona” for an exhilarating whale-watching adventure.
    This vessel is designed for barefoot comfort. Guests are encouraged to wear shoes that are easy to remove or simply enjoy the experience barefoot.
    From December to March each year, hundreds of humpback whales migrate from the cold…
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What's Included
  • Maui’s only floating tiki bar!
  • Experienced Captain and Crew
  • Underwater hydrophones to hear whale songs
  • Dolphin encounters on occasion
  • 21+ years 2 adult beverages
  • Soft drinks, juice, water
  • Light Snacks
  • Island-Style music
  • Two restrooms on board
What's Not Included
  • Cash gratuities for the crew
  • Hotel Pick-Up and Drop-Off
  • Parking Validation
  • Towels, Sunscreen
Additional Information

Experience the awe-inspiring humpback whales on this memorable whale watching cruise departing from Maalaea Harbor. Embark on the Hawaiian-crafted catamaran, Winona, and take in breathtaking views of Maui’s coastline while discovering fascinating facts about these remarkable marine creatures. Hear their enchanting songs through underwater hydrophones…

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Location
233 Maalaea Rd
Maalaea Road
Google Maps 233 Maalaea Road, places you in front of US Coast Guard building. The pier is to your left. Walk onto the pier, turn left, and go to the very end. Look for our sail catamaran is called "Winona" for check in.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.7
(14 Ratings)
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1 star
Goonvacay
Jan 28, 2026
Spectacular - Absolutely magnificent trip with awesome crew. Best whale watching we’ve ever done here on the island. Would highly recommend this tour
Review provided by Tripadvisor
Charles_f
Jan 24, 2026
A Great Experience - We came to see whales. What did that mean? Well, we discovered that our captain and guides would show us how to look for signs of their presence and how to communicate with the captain when we spotted them. That the water of this particular place was a nursery for newborns and young whales, thanks to relatively shallow water—which is warmer and less hospitable to possible predators. We would eventually recognize newborns trying out their bodies, learning how they work and getting stronger, their mothers immediately nearby to offer instruction or a rest on top of them when tired. We learned that the mother whale and calf have an escort whale that runs interference for protection, suggesting a broader community and culture of whales, including their unique vocalizations. (One of the guides would later lower a microphone into the water to share their sounds and exchanges, the specific ones of this particular group.) All of this sparked questions and conversations. And we saw whales. Small ones learning to articulate their limbs. Adults breaking the surface in a long arc before a dive or the display of a full tail. And breaches, including a nearly complete one as our fifty foot catamaran headed back to dock, eliciting the loudest cheers. The captain and crew provided an outstanding experience, building our awareness of the particular environment and why the whales chose it for bearing and preparing their young for the next steps in their lives. We learned some of what’s known about humpback whales and gained a sense of what remains unknown. In general it was a fantastic experience, not to mention the sun and water, wind and waves. Honestly, it couldn’t have been better, with the captain and crew sharing their knowledge, passion and understanding of the whales in a casual and generous way. In every sense it was a great experience.
Review provided by Viator
L9660fjtiffanyo
Jan 24, 2026
Amazing! - What an amazing experience with sunset cruise and whale watching on Winona! The crew was awesome, fun and very knowledgeable about the area and whale migration, sonar underwater to listen to the whales was a bonus. Highly recommend this tour and looking forward to more tours in the future with this company.
Review provided by Tripadvisor
Thrice4life
Jan 17, 2026
best whale watch i have done out of maalaea harbor - went whale watching today and was highly impressed with the crew and captain we got to see baby whales and breaching and fin action. would definitely do it again . Captain Keone knew when to keep going and when to stop with whales . we saw several other boats waiting for whales in the distance waiting for something only for where we went to have whales popping out . definitely a knowledge and friendly crew that make a pretty good mai tai .
Review provided by Tripadvisor
Lsn2
Jan 11, 2026
Very fun whale watching adventure. The boat is just the right size and the enthusiasm of the crew is genuine and fun! - Very enjoyable whale watch! The boat was clean and organized and just the right size. The crew was skilled and as enthusiastic to see whales and wildlife as the patrons. Will definitely sail with Winona again!
Review provided by Tripadvisor
Storyteller614881
Jan 5, 2026
2.5 hour-long tour with plenty of whale sights - We had a pleasant and exciting trip on Sail Winona on January 4, early afternoon. The boat is small with about 30 passengers only which created a family-like atmosphere aboard. The crew members helped make our experience unique. Multiple whale sights and even a shale of dolphins swimming near our boat - all that is unforgettable. The 2.5h trip duration was an important factor to increase our chances at multiple sights.
Review provided by Tripadvisor
Johnpc2314pg
Jan 5, 2026
Big fun on the Winona - We really enjoyed our whale-watching trip on the Winona with Captain Matt, Carl, and Megan. They were knowledgeable, friendly, and just plain fun. We saw a ton of whales and some dolphins too. Highly recommended.
Review provided by Tripadvisor
Tcopulos
Dec 30, 2025
Spectacular whale show - A last minute booking for a whale watching cruise turned into a spectacular experience. Within just a few minutes of leaving the harbor we saw a baby whale breaching. This area of Maui is where humpback whales deliver their babies, nurse them and then lead them back to Alaska in May. Captain Keone was ahead of all the other boats searching for whales, finding spots where they most likely would be, while the others were just chasing after them. Karl was quick on the bar serving drinks included with your ticket. Megan was the look out guiding the captain to the whales. It ended up being one of the best tours on our trip. Over the 2.5 hour cruise we saw 4 sets of mother and baby whales, many breaches and had a fun time. I would highly recommend this trip.
Review provided by Tripadvisor
Karyn_k
Dec 26, 2025
Whale watching with the family ages 29-84!! Great time! - The crew were amazing and took great care to help with my 80+ year old parents! Our entire family had a great time and were able to see several whales even early in the season!
Review provided by Viator
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