Set Sail on a Classic Hawaiian Adventure

Discover Maui’s only floating tiki bar aboard a hand-built catamaran, Hawaiian captained & operated for a truly local experience.

Discover Our Signature Maui Sailing Tours

Experience Maui’s only floating tiki bar on a hand-built, Hawaiian-captained catamaran.

Sunset Sailing on a Floating Tiki Bar Catamaran

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Unwind as the sun sets over the Pacific, with handcrafted cocktails from Maui Brewing Co. and tropical vibes from our open-air tiki bar. Includes pupus (light snacks), open bar, soft drinks, and island tunes.

Afternoon Turtle Town Snorkel at Coral Gardens

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107

Warm afternoon sun, calm waters, and sea life below — this relaxed adventure includes all snorkel gear, floating mats, refreshments, and expert Hawaiian crew.

Morning Turtle Town Snorkel at Coral Gardens

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100

Start your day with crystal-clear waters and friendly turtles at Coral Gardens. Includes snorkel gear, flotation devices, snacks, drinks, and a certified guide.

Whale Watching Cruise from Maalaea Harbor

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On this epic whale watching tour, you’ll have a close-up view of these majestic marine mammals. Watch them play in their natural environment while our crew shares insights into their behavior and biology.

Why Choose us for Your Maui Sailing Adventure?

Safety First

Coast Guard-certified, fully insured, and crewed by experienced professionals for peace of mind.

Small Group Sizes

Limited to 49 guests for a more intimate, laid-back, and personal sailing experience.

Floating Tiki Bar

Maui’s only floating tiki bar, enjoy handcrafted cocktails and local brews as you sail.

Rooted in Tradition, Powered by Aloha

Sail Winona is a hand-built Hawaiian catamaran with deep island roots, not just a tour, but a true Maui experience. As the island’s only floating tiki bar, we blend comfort, craft cocktails, and island vibes on every sail.

Locally captained and operated, we offer intimate, authentic adventures, from snorkeling at Turtle Town to relaxing sunset sails — all with safety, aloha, and unforgettable memories.

TripAdvisor Travelers’ Choice Award Winner

Recognized for exceptional service, unforgettable experiences, and top-rated sailing in Maui.

SAIL WINONA

Loved by Guests from Around the World

Consistently praised for our crew, cocktails, and overall experience.
Maui’s only floating tiki bar with handcrafted cocktails and island vibes.
From snorkeling with turtles to sunset sails, every tour is unforgettable.
Experience the magic of sailing on a classic catamaran made with aloha.

Moments from the Water

Guest Experiences That Speak for Themselves

From unforgettable sunsets to laid-back snorkeling adventures, our guests share what made their Sail Winona experience so special.

Ernest A

My son and I went on this trip and had a great time! Captain was very friendly nice and had good jokes, the staff was friendly very helpful way worth the price 3 hours is plenty of time the location where they take you is perfect plenty of turtles swimming near can’t say anything but great things about the whole experience

Alex C

Amazing trip with my wife! The 3 hour experience was a perfect time with the captain and the crew. They value what they do and take pride in their profession. Highly recommend them and will be here soon!

Amber M

We had an absolute blast! Great experience snorkeling and the Captain was great at finding so many whales. One even swam under the boat. In addition to the Captain there were 2 crew members who were wonderful and attentive. They provide a tasty breakfast and lunch spread complete with non-alcoholic and alcoholic beverages. I would definitely come again!

Alisa L

Captain and crew were professional and fun. We saw so many turtles and had an amazing time. Definitely would book again, it’s nice to be with a smaller group.

Corinne V

The Boat was huge with lots of room. Crew was super friendly and helpful. Capt. Keone kept us laughing and lead a smooth and comfortable sail. Best cruise I’ve been on since i can remember. Highly recommended!!

Kyle G

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.

Makena C

We were on the Winona 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.

sunsetlife2023

I love watching the sunsets on Maui but this sail boat “Winona” was my best experience ever. The crew is amazing and the music was fantastic. I love it how they arrange everything to be right in front of the sunset and take photos of a lifetime. Can’t wait to do it again.

Canli M

Wow! What an amazing moment to watch humpback whales in a competition pod and we got to do it on the sailboat Winona. The Captain and crew were phenomenal in their attentiveness to us. I highly recommend sailing with this company

Billej

The sunset cruise is beautiful. Sven, Carl and Megan were our crew and they made everything friendly and chill. We even brought a toddler and they made her feel so welcomed.

Craig V

Great crew, great views, and the winds were just right for sailing. The food and drinks were the usual cheese/crackers/veggies, but the focus was the sunset and it didn’t disappoint. Spectacular view.

Jason S

Great experience. Wonderful crew. Beautiful tour. An absolute must for Maui travelers. Free drinks, both alcohol and non-alcoholic type and snacks. Kid friendly.

Your Maui Adventure Starts Here

Escape the crowds and sail the island in true Hawaiian style where handcrafted cocktails, stunning views, and unforgettable moments await.