Maalaea Sunset Sail on the Floating Tiki Bar Catamaran Winona

Overview

The Maalaea sunset sail on the Winona is a 2-hour cruise from 4:30 to 6:30 PM on a Hawaiian-built catamaran with a floating tiki bar, open bar, appetizers and island music, leaving Maalaea Harbor's north dock. It suits groups who want drinks and a social deck rather than a quiet sail. The main drawback: up to 49 guests.

Highlights

• Departs Maalaea Harbor at 4:30 PM with 4:00 PM check-in and returns about 6:30 PM (sailwinona.com, October 2026).
• Open bar with Maui Brewing Co. beer, seltzers and Hawaiian cocktails plus soft drinks, juice and water, and pupu-style appetizers are included.
• From $99 on the operator site; Greetwell lists $137.51 adult and $114.56 child 5 to 12, and To-Hawaii says ages 0 to 5 ride free if you call ahead.
• The Winona is a hand-built Hawaiian catamaran with two restrooms that moved to Maalaea after surviving the 2023 Lahaina harbor fire; the operator caps groups at 49.
• Whale watching is part of the sail from December through April; spinner dolphins are possible year round.

What to Expect

1. Check in at 4:00 PM at 233 Maalaea Rd, the north dock to the left of the Coast Guard station in front of the condo building and gravel lot; look for the Makena Coast Charters signs.
2. Remove your shoes to board; the Winona is a barefoot vessel with a large step and short stairs, and is not wheelchair accessible.
3. The catamaran sails out of Maalaea along the south and west Maui coast while the crew opens the bar and serves appetizers.
4. In whale season (December to April) the captain slows for humpbacks; otherwise the crew watches for spinner dolphins and turtles.
5. The boat positions for sunset with island music playing, then returns to the north dock around 6:30 PM.
6. To-Hawaii notes the tour needs a minimum of 8 guests to run and may be cancelled for low numbers.

What to Bring

• Easy-to-remove footwear; the boat is barefoot
• A light layer for after sunset
• Motion-sickness remedy if you are prone (To-Hawaii listing)

Restrictions and Requirements

• Not wheelchair accessible (large step and short stairs)
• No outside food or drink; no pets
• Infants must sit on an adult's lap; ages 0–6 months need a parent-supplied life vest
• Not recommended for guests with poor cardiovascular health or mobility issues
• Minimum 8 guests for the sail to run; maximum 49

Cancellation Policy

Full refund with at least 24 hours' notice for groups of up to 4; groups of 5 or more must cancel 48 hours ahead and private charters 7 days ahead. If the operator cancels for weather or mechanical reasons you get another date or a full refund, and the sail may be cancelled if fewer than 8 guests book. The operator's own terms page states only that late cancellations or no-shows may forfeit payment. Checked October 2026 on Greetwell and sailwinona.com.

Location

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Wailuku, Maui, Hawaii

Meeting Point

Maalaea Harbor north dock, 233 Maalaea Rd, Wailuku, HI 96793, left of the Coast Guard station in front of the condo building and gravel lot

Check-In

4:00 PM, 30 minutes before the 4:30 PM departure

Parking and Getting There

Gravel lot by the dock and a free lot nearby per The Abroad Guide; parking validation is not included

Frequently Asked Questions

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