Why Us?
SAIL WINONA
5 REASONS TO BOOK WITH SAIL WINONA
Sail Winona is Hawaiin-owned and operated. Our captain and crew have been in business for 30 years and have received over 1,000 five-star reviews. We feature Maui’s only floating tiki bar – serving handcrafted cocktails and tasty pupus. Our classic catamaran offers plenty of space, shaded seating, and two restrooms.
We are excited to share our passion for sailing and are dedicated to providing each guest a safe, fun, and memorable experience. We appreciate your patronage and welcome you with aloha. Read on to discover why we are the best choice for an unforgettable Maui sailing or snorkeling adventure tour.
SAIL WINONA
01
Relaxed, safe environment for all ages
We believe sailing should be fun and stress-free for everyone, from first-time snorkelers to seasoned ocean lovers. With calm waters, plenty of space, and a welcoming crew, we make it easy to relax and enjoy Maui’s beauty.
02
Over 30 years experienced captains and crew
With over 30 years of experience, our Hawaiian captains and crew know Maui’s waters inside and out. Safety is our top priority, and we’re here to ensure every tour is smooth, fun, and unforgettable.
03
Hawaiian Operated with True Aloha
Sail Winona is Hawaiian captained and operated, offering a true local experience rooted in the spirit of Aloha. Our crew shares not just the sail, but their culture, stories, and deep connection to Maui’s waters.
04
Classic built sailboat with maui's only floating tiki bar
Handcrafted in Hawaii, Winona is a one-of-a-kind catamaran featuring Maui’s only floating tiki bar. With open decks, shaded seating, and stunning views, it’s the perfect place to snorkel, relax, and celebrate the beauty of the islands.
05
A 5-STAR RATED UNFORGETTABLE EXPERIENCE
Looking for a 5-star experience? Then look no further! Captain Keone and crew have received over 1,000 5-star reviews while partnering with Makena Coast Charters. Together, we achieved TripAdvisor’s Travelers’ Choice Award for several years consecutively. Although Sail Winona has pivoted to start taking bookings directly, we continue to offer the same level of excellence. See some of our recent reviews below.
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.