Sunset Sail on a Small Charming Hawaiian Catamaran

Experience a charming Hawaiian sunset sail on the Winona catamaran from Maalaea Harbor. Enjoy personalized attention, spaciousness, and stunning photo opportunities!

Duration: 2 hours
Cancellation: 1 day learn more
Highlights
  • 233 Maalaea Rd - Treat yourself and your loved ones to experience a beautiful sunset sailing cruise and Whale Watching (Dec-Apr) on our Charming Small Hawaiian Catamaran “Winona”. Hawaiian-built, well-kept & spacious catamaran where you’ll experience true Aloha hospitality, Hawaiian pupu, non-alcoholic beverages, refreshment drinks, and much more. Bring your own drinks on board for more fun. Lovely atmosphere and awesome photo opportunities! - The chance to see spinner dolphins, whales, and other sea life while we’re out! End a day in Maui on a high note when you book this fun cruise from Maalaea.

Winona will sail you away until the sun starts to dip below the horizon. You’ll have the chance to enjoy the perfect view of West Maui’s mountains, Molokai, and Lanai, while you lounge on our decks or main floor. Each year, from November through May, thousands of migrating humpback whales journey from chilly Alaska to the warm waters of Maui to breed and give birth. Our guests can get a close-up view of the majestic marine mammals on this tour. These whales play, breach, and interact in their natural environment, and our crew provides insights into their behavior and biology.

What's Included
  • Experienced Captain and Crew
  • Island-Style Music
  • Appetizers
  • Soft Drinks, juice, water
  • Two restrooms on board
What's Not Included
  • Gratuities
  • Hotel Pick-Up and Drop-Off
  • Parking Validation
  • Bring your own drinks on board for more fun
Additional Information

Avoid the over-crowded 40-50 and some with 100-passenger boats. Maui’s sunset sail and boat trips are often overpriced and target tourists who don’t know any better. We prioritize your comfort and take 30-40 passengers max. You’ll enjoy personalized attention and plenty of space to move around. Don’t miss capturing the moment when our colorful sails open – it’s a sight you won’t be able to resist capturing in photos and videos!

Winona is not just any sail catamaran; she’s Hawaii’s only Hawaiian-built, well-kept, and spacious vessel. Get ready to experience true Aloha hospitality, indulge in delicious Hawaiian snacks and drinks, and so much more. Join us for an unforgettable adventure!

  • Infants and kids ages 0-5 come for free but parents must call the office to confirm.
  • If you have questions about accessibility, please call us for help.
  • Not recommend for travelers with mobility issues
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
  • This experience requires minimum of 10 traveler
Location
233 Maalaea Rd
Maalaea Road
Check-in is 45 minutes before the activity starts time. Google Maps 233 Maalaea Road, places you in front of the Coast Guard building. We are at the north dock to the left of the Coast Guard station in front of the condo building and gravel parking lot. Look for our Signs "Makena Coast Charters".
Cancellation Policy

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

Customer Ratings
4.7
(33 Ratings)
5 stars
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1 star
Barbara_f
Aug 10, 2024
Best First Night in Maui - Truly perfect, laid back, first night in Maui. Great for kids, great for adults, beautiful scenery, amazing captain and crew. 💜
Review provided by Viator
Alicia_j
Jun 18, 2024
Great sail! - Great experience! My kids enjoyed it. The cast and crew were very kind. Everyone was very hospitable and the captain let my kids “drive” the boat. Definitely recommend!
Review provided by Viator
Evgeny_s
Jun 11, 2024
I recommend it! - Excellent experience, great captain and crew and a very enjoyable sunset sail! I would recommend this company.
Review provided by Viator
Lisa_g
Apr 26, 2024
Let the Sunset Cruise begin - What a windy boat ride to watch the Sunset. I am glad I went. I wore a dress not a good idea . Don't worry about your hair it gets wind blown. I would love to go again. The Crew was friendly and great to be with.
Review provided by Viator
Jaclynp356
Apr 20, 2024
As expected! - Brandon was our captain and made the trip enjoyable! We were able to spot some whales and had a great view of the sunset. Overall it was a great experience!
Review provided by Tripadvisor
Elizabeth_s
Mar 11, 2024
A wonderful sunset sail... - A wonderful sunset sail experience with a friendly crew and clean boat. We even saw a few whales during the sail!
Review provided by Viator
Chris_w
May 31, 2024
Sunset cruise - Friendly crew and lovely sunset. Snacks were disappointing especially as I’d asked for vegetarian and there wasn’t any!
Review provided by Viator
578earlg
Apr 26, 2024
Sunset cruise review - Was windy and cool, finding the place was interesting, no office just a sign by the dock that said Sunset Cruise. The boat was not at the dock when most of the passengers arrived, so it was a little confusing. When the boat arrived the crew was friendly and helpful. Overall it was a nice experience, but expensive.
Review provided by Tripadvisor
Julia_s
Apr 1, 2024
Nice cruise - The tour operators were all very personable and fun to be around. We picked the perfect evening for this sunset cruise. The weather really cooperated. This catamaran holds fewer people than a Trilogy tour, so it was a lot nicer. There was only one thing that I wasn't all that pleased about is that on the description of the cruise, it had alcoholic drinks provided. When we arrived on the the dock, they told us that we have to go buy our own across the street.
Review provided by Viator
Jack_g
Apr 25, 2024
Disappointing outcome - Talking with one of the crew members from Pittsburgh and some other people from California. We’ve been to Maui 5 times on dinner cruises on bigger boats and would prefer a larger vessel for sure.
Review provided by Viator
Select Date and Tickets
up to 15 guests
1
Adult
September 2024
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