WAILUKU SNORKEL FIELD GUIDE
Sunset on the Winona: A Floating Tiki Bar Sail Out of Maalaea
A two-hour, small-group sunset cruise from Maalaea Harbor aboard the Hawaiian-built catamaran Winona—drinks, pupu, island music and seasonal whale watching make this guide useful for planning the outing.
Sunset on the Winona: A Floating Tiki Bar Sail Out of Maalaea.
Board a hand-built Hawaiian catamaran for a cozy, two-hour sunset sail that blends a floating tiki bar, island music and pupu with opportunities to spot dolphins and whales as the sun slips behind the West Maui Mountains.
Highlights
Outing Highlights
A hand-built Hawaiian catamaran—Winona
Step aboard Winona, a Hawaiian-built, well-kept catamaran where true Aloha hospitality is part of the cruise experience.
Floating tiki bar and island pupu
Sip tropical cocktails, locally brewed beer and seltzers from an onboard tiki bar while sampling Hawaiian pupu as the boat moves into the sunset.
Sunset, sea life and small-group vibe
Relax to island music as the sky ignites over the West Maui Mountains, with chances to see dolphins or humpback whales during season in a cozy, small-group setting.
What the day feels like
What the sail feels like
The cruise unfolds as a relaxed, two-hour loop from Maalaea Harbor: guests board Winona, settle into a small-group atmosphere, enjoy drinks and pupu from a floating tiki bar, listen to island music and watch the sun descend while scanning the water for dolphins and, in season, humpback whales.
THE BOAT
A hand-built Hawaiian catamaran—Winona
Step aboard Winona, a Hawaiian-built, well-kept catamaran where true Aloha hospitality is part of the cruise experience.
THE TASTE
Floating tiki bar and island pupu
Sip tropical cocktails, locally brewed beer and seltzers from an onboard tiki bar while sampling Hawaiian pupu as the boat moves into the sunset.
THE VIEW
Sunset, sea life and small-group vibe
Relax to island music as the sky ignites over the West Maui Mountains, with chances to see dolphins or humpback whales during season in a cozy, small-group setting.
Suitability
Who it's for
Who this cruise suits — and who should think twice.
Practical planner
Details to review before reserving
The cruise runs about two hours; humpback whale watching is promoted as a seasonal feature (typically Dec–Apr).
Plan to check in 30 minutes before your scheduled start time at Maalaea Harbor.
Meet at Maalaea Harbor (233 Maalaea Rd.) to board the catamaran Winona.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is the sunset sail?
The tour typically lasts about two hours.
Does this boat have restrooms?
Yes. There are two restrooms on board — one for Kane (Men) and one for Wahine (Women).
Where do we meet for the cruise?
Check-in and boarding take place at Maalaea Harbor, 233 Maalaea Rd., where the vessel Winona departs.
Is the vessel wheelchair accessible?
No. The vessel is not wheelchair accessible; boarding requires a large step and short stairs.
What beverages and food are served?
The floating tiki bar offers an open bar with locally brewed beer, seltzers and Hawaiian cocktails, plus Hawaiian pupu and refreshment drinks.