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
4.7
(58 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
Francine_s
May 19, 2025
Beautiful! - Great experience, awesome crew! Made the whole evening fun good drinks, good music, we definitely recommend!
Review provided by Viator
Khojlo
May 6, 2025
Excellent experience and friendly staff - After looking around at different options from different provided, we booked this Sunset Sail and came back really really happy. It was a smaller catamaran (as advertised) and the staff was really professional yet friendly. They took time to get to know everyone on boat and kept serving appetizers/snacks/fruits and even drinks (bringing to wherever you might be sitting/standing on the boat). We had a great sunset view and the staff even alerted us the right time to take photos and even took photos for most of the guests onboard. Overall, we had a great time. I would highly recommend them to everyone.
Review provided by Tripadvisor
Deborah_s
Apr 28, 2025
Awesome - It was fun for rverone, they allowed you to walk all over the sail boat barefoot, it was a beautiful sunset, we were lucky and seen whales and dolphins
Review provided by Viator
David_s
Apr 13, 2025
Maui Sunset Cruise - Great sunset cruise! Friendly captain and crew. Was a windy day so we weee able to sail around the Au’au channel. The captain took us to some great locations to get great views of the sunset and pics during golden hour. I highly recommend and they provide snacks and beverages both alcoholic and nonalcoholic.
Review provided by Viator
Sean_m
Mar 2, 2025
The. Cruise was for a... - The. Cruise was for a sunset, and we got some amazing whale pics! We would do this one again and again.
Review provided by Viator
Dana_b
Feb 20, 2025
Perfect Sail - Perfect sunset sail. Not a big crowed boat, just the right amount of people. Friendly staff, beautiful sunset, lots of whales and very relaxing
Review provided by Viator
John_d
Feb 19, 2025
Great Sunset Cruise - Had an exceptional time. Great time on the water. A bunch of whales and great crew to make it a special evening. One of our favorite excursions during our Hawaii vacation
Review provided by Viator
Lori_b
Feb 13, 2025
Wonderful Find!! - Best sunset cruise with an amazing staff - great catamaran Really enjoyed our experience - highly recommend
Review provided by Viator
Randi_d
Apr 3, 2025
Awesome sunset & WHALES! - Had a great time! The crew is awesome, so nice and friendly. We ended up seeing a bunch of whales breaching at sunset and they took out sonar equipment so that we could listen to their calls. The drink selection was limited and the snacks were so so, but overall the experience was amazing!
Review provided by Viator
Katie_h
Apr 24, 2025
Just OK - This is a budget cruise… boat is small and the appetizers are cheese and crackers, basic local beer and seltzer brinks no mixed cocktails. The staff was great and very friendly. Last 10 minutes of cruising is a view of the sunset. This cruise is very basic and not worth the money.
Review provided by Viator
From $119
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).