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Experience Maui’s stunning sunset aboard a small, Hawaiian-built catamaran with drinks, snacks, wildlife sightings, and an intimate atmosphere for $119.

The Sunset Sail on a Small Charming Hawaiian Catamaran from Maalaea Harbor offers an inviting 2-hour escape into the beauty of Maui’s evening sky. Priced at $119 per person, this tour is ideal for those seeking a relaxed, personal sailing experience with a maximum of 40 passengers. The vessel is locally built, emphasizing quality and genuine Hawaiian craftsmanship, which adds an authentic touch to the voyage.
This tour stands out for its intimate size, promising personalized attention and a more laid-back atmosphere compared to larger boats. It departs at 5:00 pm from Maalaea and offers a chance to witness the Hawaiian sunset, along with wildlife sightings such as dolphins, whales (in season), and other marine creatures. With delicious Hawaiian snacks and an open bar, it appeals to those looking for both scenic beauty and a taste of local hospitality. While the tour is generally well-loved, potential guests should be aware that sails are not always raised due to weather conditions, which might disappoint those specifically hoping for a sailing experience.
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The tour begins at 233 Maalaea Rd, Wailuku, HI 96793, a location near public transportation options. The meeting time is at 5:00 pm, and the boat ends back at the same point. The small size of the vessel allows guests to move freely around the boat, walk barefoot, and enjoy unobstructed views of the horizon.
Guests are encouraged to arrive early to settle in comfortably, as the boat accommodates up to 40 travelers, making it a cozy yet spacious setting. As this is a mobile ticket experience, no additional transportation or parking validation is included, so plan accordingly.

The Winona is the only Hawaiian-built, well-maintained, and spacious catamaran on this tour. Its design emphasizes comfort and style, with two restrooms onboard and ample space for guests to relax and socialize. The floating Tiki Bar serves Hawaiian pu pu’s—local-style snacks—and offers a full open bar.
The crew is led by an experienced captain, noted for friendly and attentive service. The vessel’s small size makes it ideal for a more personal sailing experience, often leading to better interactions with the crew and fellow guests.

The main highlight is watching the Hawaiian sunset, which provides a vibrant backdrop for photos and peaceful moments. The golden hour views are particularly impressive, with some reviews mentioning excellent vantage points for capturing photos.
Along With the sunset, guests have a chance to see dolphins and whales—especially from December through April when whale season peaks. Some guests report listening to whale calls with sonar equipment, adding a unique dimension to the wildlife experience. Dolphins are often spotted during the cruise, sometimes breaching near the boat.

The floating Tiki Bar offers a selection of Hawaiian cocktails, local beer, seltzers, soft drinks, and refreshing juices. Guests are welcome to bring their own beverages to enjoy during the cruise. The island-style music creates a laid-back, festive atmosphere, perfect for unwinding as the sun dips below the horizon.
Onboard Hawaiian pu pu’s (appetizers) are served, including cheese and crackers and other simple snacks. While some reviews mention the snacks as basic, the focus remains on the relaxing environment and spectacular scenery.
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While the majority of reviews praise the gorgeous sunset views and friendly crew, there are mentions that sails are not always hoisted. This results from wind conditions on the day of the tour, which is entirely at the captain’s discretion. Some guests note that the tour is more of a boat ride than a sailing adventure, but views of the sunset still impress.
Guests should dress comfortably, keeping in mind that hats may not stay on due to wind. The boat is not recommended for travelers with mobility issues, and the tour requires good weather. In case of poor weather, full refunds or rescheduling are offered.

With a maximum of 40 travelers, the tour delivers a relaxed and intimate environment. Reviews highlight the friendly, attentive staff and their willingness to accommodate guest needs. The pace is leisurely, allowing plenty of time to chat, take photos, and enjoy the scenery without feeling rushed.
Guests often mention the calm and welcoming atmosphere, making it suitable for families, couples, and small groups. The small vessel size provides an advantage over larger cruises, minimizing crowds and promoting a more personal experience.

The tour does not include hotel pickup or drop-off, so guests should plan to arrive at the meeting point. The boat is not recommended for travelers with mobility issues due to the nature of the vessel and the weather considerations. Infants 0-6 months must bring a coast guard-approved life vest.
Guests are advised to arrive early and dress in layers, as it can get windy on the water. Sun protection is unnecessary in the evening, but bringing a light jacket is wise. Cancellation is free if done at least 24 hours in advance, with weather being a key factor in any possible cancellations.
This tour excels for those seeking a relaxed, small-group setting with personalized service. It’s perfect for romantic evenings, family outings, or small groups of friends. The authentic Hawaiian feel, combined with delicious snacks and drinks, makes it a memorable way to end a day in Maui.
While it may not satisfy travelers looking for a sailing adventure due to weather constraints, the scenic views and friendly crew help compensate. The wildlife sightings and stunning sunsets often leave guests with lasting impressions.
The Sunset Sail from Maalaea Harbor offers a value-rich experience that balances beautiful scenery, local hospitality, and intimate surroundings. The $119 price includes snacks, an open bar, and plenty of opportunities for wildlife viewing. The small vessel size enhances comfort and interaction, making it particularly suited for those who prefer a more personal experience.
Limitations include weather-dependent sailing and basic snacks, but these are minor compared to the gorgeous sunset views and friendly atmosphere. This tour fits well for anyone wanting a relaxed, scenic evening on Maui with the chance to enjoy local marine wildlife in a personalized setting.
“Great sunset cruise! Friendly captain and crew. Was a windy day so we weee able to sail around the Auau channel. The captain took us to some great …”
What time does the tour start?
The tour departs at 5:00 pm from Maalaea Harbor.
How long does the tour last?
It lasts approximately 2 hours.
Are drinks and snacks included?
Yes, Hawaiian snacks and an open bar with alcoholic and non-alcoholic beverages are included.
Is sailing always part of the cruise?
Sails are not always hoisted due to weather conditions; the crew decides based on wind.
Can I bring my own drinks?
Yes, guests are welcome to bring their own beverages to enjoy onboard.
Is this tour suitable for children?
Yes, small children can participate, but infants under 6 months need a coast guard-approved life vest.
Is parking available?
Parking validation is not included, so guests should plan accordingly.
What is the cancellation policy?
Full refunds are available if canceled at least 24 hours before the scheduled start.
Is the tour accessible for travelers with mobility issues?
No, it is not recommended for those with mobility challenges.
What should I wear?
Dress comfortably in layers, and bring a light jacket for wind and evening chill.