Floating Tiki Bar Sunset Sail Maui

Unique Cocktail Cruise

Set sail from Wailuku on Maui’s northwest coast for a two-hour tiki bar sunset cruise. As the sun dips, witness vibrant oranges and pinks painting the sky, with Lanai and Molokai framed in the distance. Priced at $119, this unique experience offers a genuine Hawaiian vibe, unlike traditional party boats. Enjoy tropical drinks and island music as the catamaran gently rocks. Book through CheapHawaiian.

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran f-1

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran f-2

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran f-4

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran f-5

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran f-7

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran f-8

Activity Price

119 USD

Duration

2 Hours

Age

All Ages

Location

Wailuku, HI

Amenities

Tropical cocktails and beverages are included, and this isn't a one-drink-then-pay situation — the tiki bar is stocked and flowing for the full two hours. In practical terms, that means you step aboard, get a drink in hand within minutes, and spend the sail actually relaxing instead of flagging down crew or watching a tab grow.

Live island music sets the tone from departure to docking, and on a catamaran this size it hits differently than a speaker system blasting from a stage — it fills the whole boat without overwhelming conversation. You can settle into the netting stretched between the hulls with your drink and let the music and the motion of the water do the rest.

Special Instruction

Tiki Bar, Open Ocean, Maui Sunset

That First Drink Leaving the Harbor

There’s a specific moment right as the catamaran clears the harbor mouth and the open Pacific opens up ahead of you — the sails fill, the engine quiets, and someone hands you a cold tropical cocktail. The sound shifts from marina noise to wind and water, and you realize the next two hours belong entirely to you.

Lanai Going Purple on the Horizon

About an hour in, the light goes golden and Lanai starts turning shades of purple and charcoal across the channel — the kind of view that makes everyone on the boat go quiet for a few seconds before the music brings you back. The catamaran holds position just long enough for the full color show, hulls rocking gently in the swell while the sky does something different every minute.

Live Music Carrying Across the Water

The onboard musician has a way of finding exactly the right song for the moment — something slack-key and unhurried while the crew refills your drink and the coastline slides slowly past. You can feel the guitar through the deck if you’re sitting close enough, and the notes blend into the wind in a way that no speaker system ever quite manages. By the time the second round hits, half the boat is swaying without realizing it.

Tiki Bar Sunset Sailing Includes

About

Additional information

Pricing

Cancellations

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.

Floating Tiki Bar Sunset Sail Maui — Frequently Asked Questions

How many drinks are included on the Maui floating tiki bar sunset sail?
The open bar is included for the full two hours of the sail, so there’s no drink limit or ticket system — you drink what you want within that window. The bar is stocked with tropical cocktails and other beverages, and the crew keeps things moving so you’re not waiting around between rounds.
Is the floating tiki bar sunset sail good for people who get seasick?
Catamarans are significantly more stable than single-hull boats, which helps, but this is open ocean sailing off Maui’s coast and there is real swell depending on the day. If you have any history of motion sickness, take a non-drowsy seasickness remedy like Bonine about an hour before boarding, and position yourself toward the middle of the boat near the waterline rather than at the bow.
Where exactly does the Maui tiki bar sunset sail depart from?
The departure point is listed as Wailuku, HI — exact marina or dock details will be confirmed in your booking confirmation through FareHarbor. Give yourself extra time to find parking and check in, especially during peak season when the harbor area can be busier than you’d expect in the early evening.
Can kids come on the floating tiki bar sunset sail in Maui?
Yes — this activity is listed as all ages, so keiki are welcome aboard. That said, it is a cocktail cruise at its core, so the vibe is adult-social; it works best for families with older kids who are comfortable on boats and happy to hang out for two hours on the water without structured activities.
What should I wear on the Maui sunset catamaran cruise?
Wear something comfortable and casual — light summer clothes, a swimsuit underneath if you want, and soft-soled shoes or sandals that can handle a wet deck. Pack a thin layer for the ride back; once the sun sets and the boat is moving, the trade winds get real and people in tank tops are usually the ones wishing they’d planned ahead.
Is this the same as a regular Maui sunset cruise, or is the tiki bar thing actually different?
It’s genuinely different in feel — the catamaran is styled as a floating tiki bar with a character and aesthetic that sets it apart from the larger, more corporate sunset cruise boats that run out of Lahaina. It’s a smaller, more intimate setup with live island music rather than a DJ, which means you’re actually able to talk story with the people around you instead of just standing in a crowd watching the same sunset through your phone.

More Snorkeling Tours

Floating Tiki Bar Sunset Sail Maui