About Us
SAIL WINONA
A Classic Hawaiian Experience — Captained by Locals
At Sail Winona, we’re more than just a boat — we’re a piece of Hawaii’s rich seafaring history. Hand-built and lovingly maintained by locals, our classic catamaran offers a one-of-a-kind way to connect with the magic of Maui from the water.
Here, you can slow down, take in the moment, and make memories that will last a lifetime — all while experiencing the true spirit of aloha.
SAIL WINONA
Our Story
Classic Hawaii, Intimate Experience
Local Connection, Small-Group Experience
We’re proud to be **Hawaiian-captained and operated**, with a crew who know these waters like the back of their hand — from sheltered reefs rich in sea life to the best sunset view over the Pacific. Our team is passionate about sharing their knowledge, stories, and the magic of Maui with every guest on board.
With a small number of passengers (up to 49) per tour, we’re able to keep your experience comfortable, welcoming, and much more personal — ensuring you feel less like just another tourist and more like a cherished friend.
Maui’s Only Floating Tiki Bar
Sail Winona stands out as **Maui’s only floating tiki bar**, serving up handcrafted tropical drinks made with **Maui Brewing ingredients** — a blend of classic island flavor and pure relaxation at sea. Our team carefully prepares each cocktail, using the finest local ingredients to capture the spirit of Hawaii in every sip.
Sip a Mai Tai, watch the sunset illuminate the Pacific, or celebrate a special moment with friends, family, or someone you love — there’s something truly magical about toasting to paradise from our decks. Let the gentle waves, the soft glow of sunset, and the warmth of Aloha make your time on board an experience you’ll remember for years to come.
Maui’s Only Floating Tiki Bar
Sail Winona stands out as **Maui’s only floating tiki bar**, serving up handcrafted tropical drinks made with **Maui Brewing ingredients** — a blend of classic island flavor and pure relaxation at sea. Our team carefully prepares each cocktail, using the finest local ingredients to capture the spirit of Hawaii in every sip.
Sip a Mai Tai, watch the sunset illuminate the Pacific, or celebrate a special moment with friends, family, or someone you love — there’s something truly magical about toasting to paradise from our decks. Let the gentle waves, the soft glow of sunset, and the warmth of Aloha make your time on board an experience you’ll remember for years to come.
Guest Experiences That Speak for Themselves
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.