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.
Afternoon Turtle Town Snorkel at Coral Gardens
- 1:00 PM (Please check in at 12:30 PM. The boat departs promptly at 1:00 PM.)
From
$
130
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
- 9:00 AM (Please check-in at 8:30 AM. The boat departs promptly at 9:00 AM)
From
$
130
Start your day with crystal-clear waters and friendly turtles at Coral Gardens. Includes snorkel gear, flotation devices, snacks, drinks, and a certified guide.
Sunset Sailing on a Floating Tiki Bar Catamaran
- 5:00 PM – 7:30 PM
From
$
125
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.
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.
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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.
Samantha T.
Client
You can feel the heart behind Sail Winona. From the Hawaiian captains to the handcrafted boat, everything felt authentic and personal.
Jessica M.
Client
Loved the small group setting. We got up close with sea turtles and then relaxed with a local beer on deck. Already planning our next trip.
David R.
Client
We did the sunset sail and it was magical. The floating tiki bar is such a vibe, great drinks, incredible views, and the crew made us feel valued.
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.