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: 24 hours
Highlights
  • 233 Maalaea Rd - Indulge in a delightful Sunset Sailing Cruise and Whale Watching (Dec-Apr) on our charming Hawaiian Catamaran. “Winona” is the only Hawaiian-built, well-maintained, and spacious catamaran where you can enjoy genuine Aloha hospitality. Our floating Tiki Bar offers Hawaiian pu pu’s, an open bar with locally brewed beer, seltzers,…
What's Included
  • Experienced Captain and Crew
  • Open bar (beers/seltzers/cocktails) soft drinks, juice, water
  • Appetizers
  • Island-Style Music
  • Two restrooms on board
What's Not Included
  • Hotel Pick-Up and Drop-Off
  • Parking Validation
  • Gratuities
  • For infants 0-6 months old parents must bring a coast guard approved life vest
Additional Information

Discover the resilience and spirit of Maui on the Winona, a vessel that courageously withstood the Lahaina harbor wildfires, now anchored outside the harbor breakwall. Currently operating from Ma’alaea Harbor, guests are invited to join the captain and crew on an inspiring journey across the stunning Pacific waters. Having overcome significant…

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
4.8
(78 Ratings)
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Christopher
Aug 7, 2025
Captain Keone is the best!! - This is just as described. Small group, excellent staff, Captain Keone is the best!!! You looking for a small group sunset cruise, this is it!!
Review provided by Tripadvisor
Karrie_w
Jul 26, 2025
It was a nice ride and... - It was a nice ride and the staff is amazing. The food was also good. They had a great selection of drinks.
Review provided by Viator
Z4548oomathiasb
Jul 25, 2025
- My girlfriend and I booked the sailing adventure and had a great time. The staff were extremely warm, friendly, and were also having fun. That created environment for the guests to mingle amongst s themselves and so we met many people all with different stories. In addition, there were plenty of beer, seltzers, and cocktails while on board. The views were amazing and the trip lasted longer than the 2 hours advertised.
Review provided by Tripadvisor
Jenniferu941
Jul 25, 2025
Golden Sunset Views - My husband booked this adventure for our vacation. He chose an excellent adventure. The crew is magnificent! The beverages were flowing, conversations a going, and snacks being eaten. They knew just how to make our 11 year old son's night by asking him to help "drive" the catamaran. Talk about smiling from ear to ear. Thank you again for making a core memory.
Review provided by Tripadvisor
Rebeccach920xv
Jul 24, 2025
- What an amazing experience and such a beautiful way to see the sunset. The crew was FANTASTIC and they went above and beyond to help my mom, who has mobility issues on and off board. Highly recommend this cruse.
Review provided by Tripadvisor
Kolby_h
Jul 19, 2025
Worth it 100% - The crew was awesome and made for great vibes. Would highly recommended this to anyone who wants to watch the sunset with good drinks and good times.
Review provided by Viator
Desiree_f
Jul 17, 2025
Excellent!! - Very friendly staff. Amazing experience. Would highly recommend this adventure. Good food and drinks too
Review provided by Viator
William_s
Jul 14, 2025
Fun sunset cruise - Fun cruise with plenty of room to move about. The crew was very friendly and accommodating. Captain actually set both the head and main sails for awhile and got us up to about 10 knots. There are plentiful snacks and beverages from the tiki bar. We cruised for about 2.5 hours and enjoyed a magnificent sunset. Be sure to read your reservation information completely to get the directions to find the boat. It is tucked in front of the condos at one end of the marina. I didn't see any signage and several of us had a little difficulty finding it. Definitely worth the search in the end.
Review provided by Viator
Jabba22
Jun 10, 2025
Wonderful Sunset Cruise with Makena Coast Charters! - This was a wonderful sunset cruise with Makena Coast Charters. The evening we went the weather was absolutely spectacular with relatively calm water. Although it can't be planned, we got an extra thrill when although late in the season, we had a humped back whale swim past our catamaran! We also got to enjoy a school of dolphin swimming by as well. The food and beverages provided were excellent and the whole crew was friendly, helpful, and always trying to ensure we had the best experience possible. I would highly recommend this company and especially this cruise!
Review provided by Tripadvisor
Q5171lajasons
May 31, 2025
Wonderful Experience - Great experience. Wonderful crew. Beautiful tour. An absolute must for Maui travelers. Free drinks, both alcohol and non-alcoholic type and snacks. Kid friendly.
Review provided by Tripadvisor
From $119
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).