Sunset Sail on a Charming Hawaiin Catamaran from Maalaea Harbor
4.7
28 Ratings
Wailuku
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 Sail on a Charming Hawaiian Catamaran called “Winona” a love boat that will do her magic to make sure you’ll fall in love all over again.

Winona is Maui’s only Hawaiian-built, well-kept & spacious catamaran where you’ll experience true Aloha hospitality, Hawaiian pupu, refreshment drinks, and much more.

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.

As the sun sets & we sail back, you’ll know that you have been treated to a truly magical experience to a perfect way to end your perfect day in paradise.

What's Included
  • Appetizers
  • Soft drinks, juice, water
  • Experienced captain and crew
  • Island-style music
What's Not Included
  • Gratuities
  • Hotel Pick-Up and Drop-Off
  • Parking Validation
  • Bring your own drinks on board for more fun
Additional Information

Steer clear of the packed boats capable of carrying 30-50 or even 100 passengers. In Maui, the sunset sailing and boat excursions are frequently too costly, aimed at exploiting uninformed tourists. We prioritize your relaxation by limiting our passengers to a mere 15-20. Enjoy the benefits of ample personalized attention and plenty of room for free movement. Be sure to capture the stunning moment our vibrant sails unfurl – you’ll be compelled to record it in photographs and videos!

Winona is not an ordinary sailing catamaran; she is the only one in Hawaii that is Hawaiian-made, thoroughly maintained, and roomy. Prepare yourself for pure Aloha hospitality, treat your taste buds with tasty Hawaiian goodies and beverages, and so much more. Join us for an experience that you’ll never forget!

  • 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 30 minutes before the activity start 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
(28 Ratings)
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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
Thomas_d
Mar 6, 2024
Sunset whales and drinks - One of the best sunsets I've ever seen. Cocktails were good and plentiful. The crew were all great with conversation and interaction. The whale watching was good. Caught one breach on video. Turned out to be the best cruise we went on, and we did four that week. I would recommend this be a first choice for any one planning to book cruise.
Review provided by Viator
David_f
Mar 4, 2024
Support Lahina - For a Sunset and whale watching experience, all I can say is one moment we were watching both, together at the same time, under a sky as pretty as the ceiling of the Sistine Chapel… also supporting a crew of Lahina residents as this ship previously ran out of there.
Review provided by Viator
Grace_t
Mar 4, 2024
Very attentive crew the... - Very attentive crew the captain was awesome would definitely recommend to everyone it was an awesome experience
Review provided by Viator
852makenac
Mar 3, 2024
Highlight of our Maui trip! - We were on the Wainona Sailboat with Capt Brandon, Capt Keone, Carl, Rachel & Canli and it was truly the most perfect setup. There were roughly 15 or so other people on the boat with us, plenty of room to move around and absolutely fabulous views. The crew could not have been more welcoming, attentive & genuinely enjoyable to be around. I would 100% do that again & recommend to anyone visiting Maui.
Review provided by Tripadvisor
Kylegi1544gn
Mar 3, 2024
Very pretty - The crew of capt Brandon, capt Keone, Carl, Rachel, and Canli were great! Very pretty sunset and fun atmosphere. Drinks and food were included as well.
Review provided by Tripadvisor
Z994dileer
Mar 3, 2024
Great Times! - We took the sunset and whale watching tour with Captain Keoni and crew members Branden, Carl, and Rachel. What a pleasant experience! They made us feel like we were out on a boat with old friends instead of a tour boat. Professional yet cordial and accommodating, the crew met our every need. Snacks and drinks were provided, as well as a cooling swim for anyone who wanted, where the whales could clearly heard underwater. The sunset was truly amazing, and we saw whales on the way out AND the way back. We made friends with the intimate group of passengers, and hugs were given all around upon our departure. I would HIGHLY recommend this awesome tour to anyone over the bigger companies. You will not be disappointed ppointed.
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
Cathy_w
Mar 10, 2024
Sunset Whale Watch - Crew was fantastic. Communication great. Saw some awesome whale action. This is certainly a preference related comment…but once we were out watching the whales, I would have preferred no music…maybe heard the slap of those whales on the water.
Review provided by Viator
Seastef
Mar 4, 2024
Would have been great with better expectation setting - With correct expectations, this would have been great. I am sure the residual fire chaos has contributed to the inaccurate information, so I want to be sure future guests know what we learned. 1) Capacity-- at the time of booking, the page said 10-20 passengars and the office said 10-30. We had 38 on our cruise. After our complaint, the description has been adjusted to be a max of 40, although it still says a max of 16 elsewhere. Obviously there is a huge difference between 20 and 40 people. We didn't get a single photo without others in them. And if some passengers hadn't been willing to sit on the trampolines (usually closed, but the crew opened them; passengers there were promptly completely soaked) then the crowding issue would have been even more problematic. There just isn't view seating for that many people therefore people stand blocking the path from bow to food/drinks. Moving around the ship was extremely difficult. Had we expected this, it wouldn't have been a big deal, but it was a big disappointment to us. 2) Time-- they say to check in and board 1/2 hr before departure. Check in happened and then we stood around in the sun (no seating) waiting to board. We finally did board 10 minutes before departure time and then sat around waiting for 3 people who ended up arriving over 45 minutes late (15 minutes past departure time). Since the sun was down, there was no extending the cruise later to make up for the lost time to the 35 of us who had been there prior to departure time (if not at check in time). The crew said they "just" tell people 1/2hr in advance since people are often late. That being the case, why not actually leave for an on time departure? And since you do tell people to get there, why not let them on board or at least provide seating (preferably shaded seating) for those who arrive as directed? 3) Food-- they said to notify them of dietary restrictions. We notified them that we were vegetarian. Imagine our surprise that food was just ham/cheese roll ups, ham sandwiches, and chips. The crew said to "take it up with management." Management didn't bother to respond. If you don't eat pork, expect chips to be the extent of the food available to you. Again, with proper expectations, this wouldn't have been a big deal. The crew was amazing and sailing off of Maui in whale season is a fantastic experience. Had we gone in with more accurate expectations, it would have been far more enjoyable to us.
Review provided by Tripadvisor
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