Floating Tiki Bar Sunset Sail Maui

Sunset Sailing & Whale Watching Cruise

Experience Maui’s Golden Seas Aboard the Hawaiian Catamaran Winona

Duration: 2 Hours

Meeting Point: 233 Maʻalaea Rd, Wailuku, HI 96793, USA

Cancellation Policy: 24-hour notice before the activity start time

Age Limit: 70 and under

Group Size: Small group — 30–40 guests

Accessibility: Not wheelchair accessible

Activity Overview

Set sail into the golden glow of a Maui sunset aboard the Hawaiian-built catamaran Winona — a vessel unlike any other on the island. This relaxing two-hour cruise invites you to unwind to the rhythm of island-style music while surrounded by panoramic ocean views and warm tropical breezes.

From December through April, guests are treated to the extraordinary sight of North Pacific humpback whales breaching and playing in the Hawaiian Islands Humpback Whale Marine Sanctuary — an awe-inspiring natural spectacle.

During your voyage, enjoy a drink at our floating Tiki Bar, featuring an open bar with locally brewed beers, seltzers, Hawaiian-crafted cocktails, and soft drinks. Indulge in delicious Hawaiian-inspired appetizers as you watch the sun dip below the horizon, painting the sky in shades of pink, orange, and gold. Winona offers two spacious restrooms and a comfortable layout designed for relaxation and enjoyment.

What’s Included

• Tasty appetizers inspired by island flavors
• Open bar with local beers, seltzers, and cocktails
• Juice and water
• Island-style music to set the mood
• Experienced captain and professional crew
• Whale watching opportunities (December–April)
• Sailing experience to and from your scenic destination
• Two restrooms on board

What’s Not Included

• Hotel pick-up and drop-off
• Parking validation
• Light jacket or shawl for cool evenings
• Coast Guard–approved infant life vest (for 0–6 months — must be provided by parents)
• Cash gratuities for the crew

Why You’ll Love It

This experience blends the beauty of Maui’s sunset skies with the magic of ocean wildlife and the warmth of authentic Hawaiian hospitality. Whether you’re sipping a handcrafted cocktail, spotting breaching whales, or simply relaxing under the colors of dusk, the Winona Sunset Cruise is an experience you’ll cherish long after you leave the shore.

Join us for an evening of gentle breezes, golden horizons, and pure aloha.

Check-in Details

Parking:

• Location: Ma’alaea Harbor

• Cost: $1 per hour. We recommend paying for 3 hours total.

• Payment: The parking lot uses a QR code system. Please arrive early to pay via the QR code, and be sure to have your license plate number handy.

• Parking Instructions: Please pay attention to where you park and follow the instructions on the parking signs. We are not responsible for any vehicles that are towed.

Check-in Times:

• September 1st – February 28th:

  • Check-in: 4:00 p.m.

  • Departure: 4:30 p.m.

  • Return: 6:30 p.m.

• March 1st – August 31st:

  • Check-in: 4:30 p.m.

  • Departure: 5:00 p.m.

  • Return: 7:00 p.m.

Meeting Location:

• Maalaea Harbor

• Address: 233 Maalaea Rd, Wailuku, HI 96796

• Vessel Name: “Winona” Sail Catamaran – Makena Coast Charters

Upon arrival, all guests must sign in and complete the liability waiver.

Footwear:

• Our boat is a barefoot vessel. We kindly ask that you wear footwear that’s easy to slip off or simply go barefoot while on board.

Restrictions

• Accessibility: This vessel is not wheelchair accessible. Guests with mobility challenges may find it difficult to get on and off the boat due to a large step and short stairs. We strive to ensure that everyone feels comfortable and welcomed, but please keep this in mind when booking.

Pricing

• Adults (Age 13+): US$119

• Children (Age 5-12): US$99

• Infants (Age 0-5): Free

Cancellation and Refund Policy

• Full Refunds:

  • Groups of up to 4 require at least 24 hours’ notice before the scheduled departure.

  • Groups of 5 or more require 48 hours’ notice for a full refund.

  • Private charters require 7 days’ advance notice for a full refund.

• Weather and Mechanical Cancellations:
  Cancellations due to weather or mechanical issues, even within the grace period, will be automatically honored.

• Cancellation/Change Method:
  Cancellations or changes cannot be made via email. Please text us with any changes or questions at 808-874-1273.

Special Notice

We require a minimum number of bookings for this tour to proceed. Makena Coast Charters reserves the right to cancel the tour if there is a low customer count.