Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

4.8 (31)
Wailuku, US
4.8 (31)
Wailuku, US
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Experience the magic of a Hawaiian sunset aboard the charming catamaran Winona. Avoid the crowded tourist boats and enjoy a more personalized and comfortable experience with a maximum of 15-20 passengers. As the colorful sails open, capture the moment in photos and videos that you won't be able to resist sharing. Winona, Hawaii's only Hawaiian-built vessel, offers true Aloha hospitality, delicious Hawaiian snacks, and refreshing drinks. Lounge on the deck or main floor and take in the breathtaking views of West Maui's mountains, Molokai, and Lanai as the sun dips below the horizon. This unforgettable sunset sail is the perfect way to end your day in paradise. Book your spot now!

About this experience

  • Free Cancellation For a full refund cancel at least before the start of your booking
  • Suitable for 1-15 Participants
  • Private Tour, Small Group Tour
  • Self Guided Experience
  • Personalized attention and plenty of space
  • Hawaiian hospitality, snacks, and drinks
  • Perfect view of West Maui's mountains, Molokai, and Lanai
  • Capture the moment with colorful sails
  • Truly magical experience to end your perfect day
  • Two restrooms on board
  • Appetizers
  • Soft drinks, juice, water
  • Experienced captain and crew
  • Island-style music
  • Gratuities
  • Hotel pick-up and drop-off
  • Parking validation
  • Bring your own drinks on board for more fun

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More about this experience


Experience an unforgettable adventure on the stunning island of Maui with a Sunset Sail on the charming Hawaiian catamaran, "Winona." Unlike the overcrowded and overpriced boat trips for tourists, this intimate and personalized cruise prioritizes your comfort and offers a unique sailing experience. With a maximum capacity of only 20-30 passengers, you'll have plenty of space to move around and enjoy the breathtaking views.

What to expect?

Treat yourself and your loved ones to a beautiful Sunset Sail on "Winona," the love boat that will make you fall in love all over again. As the colorful sails open, capturing the moment becomes irresistible. Get ready to indulge in delicious Hawaiian snacks and drinks while experiencing true Aloha hospitality. You'll have the perfect view of West Maui's mountains, Molokai, and Lanai as the sun dips below the horizon.

Who is this for?

This Sunset Sail is for anyone seeking a romantic and magical experience on the waters of Maui. Whether you're a couple looking for a memorable date night, a group of friends celebrating a special occasion, or a solo traveler seeking relaxation and beauty, this experience suits all. The inclusive and welcoming atmosphere ensures that everyone can enjoy the charm of "Winona" and the breathtaking Hawaiian sunset.

Why book this?

What sets this Sunset Sail apart is the personalized attention and intimate setting. With only a limited number of passengers, you'll have ample space to relax and enjoy the journey. "Winona" is not just any catamaran; she's the only Hawaiian-built vessel on Maui, offering an authentic experience. Indulge in Hawaiian snacks and drinks while being surrounded by the stunning natural beauty of the island. This is your chance to create lasting memories and witness the magic of a Hawaiian sunset.

Good to know

Check-in for the Sunset Sail is at 4:00 p.m. at Maalaea Harbor, conveniently located on Maalaea Road. Parking is available in the gravel lot in front of the condo building. The cruise includes appetizers, soft drinks, juice, water, island-style music, and alcoholic beverages. Gratuities, hotel pick-up and drop-off, souvenir photos, and parking validation are not included. Prepare to be enchanted by the beauty of the Hawaiian sunset and the warm hospitality of the crew.


Passengers who have experienced the Sunset Sail on "Winona" have praised the personalized attention and the breathtaking views. They have raved about the delicious Hawaiian snacks and drinks, as well as the warm and welcoming crew. Many have mentioned that this intimate sailing experience provided a unique and unforgettable way to end a perfect day in paradise. Don't miss your chance to be captivated by the magic of a Hawaiian sunset on this charming catamaran.

How long before the event do I need to book?

  • You can book at any time before the event

Vouchers accepted in the following formats

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4.8 (31)


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!


Excellent experience, great captain and crew and a very enjoyable sunset sail! I would recommend this company.


Friendly crew and lovely sunset. Snacks were disappointing especially as I’d asked for vegetarian and there wasn’t any!


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.


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.


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.


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!


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.


A wonderful sunset sail experience with a friendly crew and clean boat. We even saw a few whales during the sail!


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.
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2024-07-22 02:30