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

Sail Winona was constructed by skilled hands here in Hawaii, with careful attention to every detail. This catamaran carries a rich past — a blend of traditional craftsmanship, decades of seafaring knowledge, and the warm spirit of Aloha — making every voyage feel both timeless and intimate. From its strong hull to its handcrafted finishes, you can see and feel the love that went into creating a vessel designed to bring people together, foster connection, and celebrate the magic of the islands. Step aboard and let the stories of the sea become a part of your own, as you create new memories.

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.