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Maui Sunset Sails & Cruises

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Sunset Sails & Cruises Sorted by Specific Tour

Maui Sunset Sails & Cruises

Maui sunset sails are a 'classic' Maui activity. As beautiful as they are fun, these sails generally leave about an hour before sunset time so they will catch the sun going down into the ocean at the same time the colors of the clouds on the mountaintops are dramatically changing as each moment passes. Most of the sunset sails we offer are available at discount pricing.
What will a typical sunset sail include:
  • Most sunset sail boats are sail boats (some just cruise without sales) and as such they will generally raise the sails and fill them with the gentle breezes usually found off the coast at sunset time.
  • Cocktails, beer, wine or champagne, as well as appetizers are the general order of the day. 
  • Two hours is the usual timing which is just perfect for a lovely cocktail hour before dinner reservations at a fine on-shore restaurant. 
  • Generous boatloads of all the colors you can imagine.
Where will your sunset sail depart from? The three most likely departure points will be:
  • Maalaea Harbor in central Maui. From here you have a great view of the mountain of Haleakala behind you as the sun sets in the opposite direction.
  • Lahaina Harbor is the quintessential departure point for a sunset sail. Generally the port is devoid of all but the slightest of breezes until you work your way off shore to the gusts that blow between the islands of Maui, Lanai, Molokai and Kahoolawe. As the sun sets over Lanai the island of Maui behind you will be painted in colors.
  • Kaanapali Beach requires a boarding off the sand onto your vessel so it begins with a bit more adventure than most. Compounding the adventure, these boats are the quickest to find the wind line and usually provide the best actual sail experience of Maui's sunset sail departure points.

Pride of America Cruise Ship:

Sunset Sails on Maui will not pick up at the cruise boat pier but these sunset cruises can be reached via a Rent-A-Car that can be arranged through Tom Barefoot's Tours and you can be picked up by the Rent-A-Car shuttles right at the cruise ship dock. These Maui sunset sails are available on the Sunday afternoon and evening of your Maui cruise itinerary.

Checkout Tom's Tips and Insights about Maui Sunset Sails & Cruises

Tom Barefoot's Tips
  • Tom's Tips - Maui Sunset Sails and Cruises

    In the first months of my arrival on Maui in 1973 I made it a point to go out on one of the sunset sails departing out of Lahaina Harbor. The name of the boat was the Viajero and the total price for the two hour tour at that time I remember to be $6.50. It was a beautiful sail boat that glided us along the shoreline of West Maui during the most colorful of sunsets. The gentle sunset breeze blew over us as it also allowed us to power slowly into the channel toward Molokai. I remember the salty captain on that cruise as being very capable but that being a different day and time I also remember him occasionally reaching for a tin cup that I'm quite certain contained a liquid not unfamiliar to pirates of days gone past. The experience was tremendous and left an indelible image in my mind of the whole adventure. It helps me at times to remember certain 'first' experiences like this one so I can relate to the 'first' impressions that our visitors are experiencing on their first visit to the islands... read more.


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Sunset Sails & Cruises Sorted by Company

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(3 Reviews, 5 Stars)

Maui Ocean Charters

1 Activity Option

Maui Ocean Charters

Set sail with Maui Ocean Charters on their sailboat "Shadowfax". Trips are available that last anywhere from a few hours to a few days or more!
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(3 Reviews, 5 Stars)

Trilogy Excursions

3 Activity Options

64' - 55' - 51' Sailing Catamarans, 55' Sailing Catamaran, 55' Catamaran to

One of the most popular and respected boating companies on Maui is Trilogy which has been in operation here since 1973. Though being a large company now, operating seven 50' range sailing catamarans, they are still the family owned operation that was begun by Eldon Coon and his two sons, Jim and Randy. Today they offer sailing tours to Lana'i, Molokini, the West Coast of Maui and an assortment of shorter sunset and sailing options and whale watches.
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(1 Review, 5 Stars)

Alii Nui Sailing Charters

2 Activity Options

Dinner cruise with hotel pickup.

The one of a kind, luxury catamaran Alii Nui departs from Maui's Maalaea Harbor and offers a variety of sail options which include Molokini snorkel tours, sunset sails, dinner sails and whale watches. All the specialty details have been included on all its tours to provide a privileged ocean experience. Snorkel tours include hot showers on board and large terry beach towels for your personal use. Dinner cruises are limited to 32 guests and even complementary pick-up is included on its whale watches.
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(15 Reviews, 4.9 Stars)

Scotch Mist Sailing Charters

2 Activity Options

50' Sailing Yacht, 50' Santa Cruz Sailing Yacht

The Scotch Mist is a 50' Santa Cruz Sailing Yacht which carries 18 passengers and offers sailing and snorkel charters off the coast of Maui. Having been the winner of the coveted Victoria to Maui Yacht Race in 1984, this vessel is a perfect choice to enjoy the waters off the coast of Maui and Lanai. She offers sailing and snorkel tours, sunset sails, trade wind sails and whale watching in season.
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(7 Reviews, 4.9 Stars)

Pride Charters

1 Activity Option

65' Maxi Catamaran, 65' Catamaran

The Pride of Maui is one of the largest and most stable power catamarans available in Maui's fleet of boats. Leaving from Maalaea Harbor the 'Pride' offers tours to Molokini in the mornings but will also operate beautiful sunset cruises a few times a week and in addition will provide one of the most comfortable boats for whale watching in the winter months.
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(6 Reviews, 4.8 Stars)

Sea Maui

1 Activity Option

Snorkeling, Whale Watching, Sunset Sails & Private Charters

Sea Maui II is a beautiful 55 foot power sailing catamaran, and the new Sea Maui III is a 65ft luxury sailing catamaran, they both depart from Kaanapali Beach. They offer a variety of snorkeling trips, whale watching, and sunset sailing options daily. Sea Maui has consistently been awarded "Maui's Best Boat Tour" for 2017, 2018, 2019 & 2020! Food is provided by the award winning Chef Joey Macadangdang of Joey's Kitchen.
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(34 Reviews, 4.8 Stars)

Teralani

2 Activity Options

65' Catamaran, 64' Sailing Catamaran, 65' Sailing Catamaran

The 65' sailing catamarans of Teralani Charters offer snorkel sails along the West Coast of Maui as far up as Honolua Bay, offer dinner cruises leaving off the white sands of Kaanapali Beach and offer spectacular whale watches during the winter months. Sailing will generally be a part of all cruises, weather permitting, and the stiff afternoon winds off the western shores usually provide some adventure and excitement. Evenings cruises however usually just have a gentle breeze.
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(8 Reviews, 4.6 Stars)

Paragon Sailing Charters

2 Activity Options

47' Sailing Catamaran

Certainly one of the very fastest boats found in the islands is the 47' customized sailing catamaran, Paragon. Paragon Sailing Charters offers a number of choices for boat tours ranging from morning sails to Molokini; Day Trips to Lanai; Sunset Sails; and Performance Sails.
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(4 Reviews, 4.5 Stars)

Gemini Charters

1 Activity Option

64' Sailing Catamaran

Gemini Charters offers sailing tours that depart off of Kaanapali Beach and has done so for over 30 years. They offer multiple tours which include a sail and snorkel up the coast to Honolua Bay when weather permits, a delightful champagne sunset sail and whale watching tours in season. Their seaworthy 64' Sea Runner Sailing Catamaran is an excellent choice for a real sail.
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(39 Reviews, 4.5 Stars)

Hawaii Ocean Project

1 Activity Option

118' Motor Yacht.

The environmentally conscious Hawaii Ocean Project operates a number of tours out of the West Side of Maui port of Lahaina Harbor. Their touring options include day tours and ferry trips between Maui and Molokai, dinner cruises, sunset cruises, snorkeling tours to Lanai and whale watches. Marine naturalists will be on board to explain the marine life and ecological education is the underlying foundation of all its activities.
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(11 Reviews, 4 Stars)

Pacific Whale Foundation

9 Activity Options

52' and 60' Power Catamaran, 52' and 65' Power Catamaran, 65' Power Catamaran, 65' Catamaran

The Pacific Whale Foundation is one of the main companies we have on island that goes out in search of the whales during the winter months. In addition, throughout the year they also offer boat tours to snorkel at Molokini, dolphin watches that look for dolphins and snorkel off the coast of Lanai and have rigid hull inflatable tours that visit the back side of Lanai.
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Makena Boat Charters

1 Activity Option

Makena Boat Charters

If you're staying on the south shore of Maui in the Kihei area, Wailea or Makena a really good choice for a snorkeling tour would be on the 65' sailing catamaran "Kai Kanani". This boat was built in 2007 and is a state of the art custom motorized sailboat. The location of the departure point for this boat is one of the very best because it is located just off the coast of Molokini, perhaps a short fifteen minute ride away.
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Makai Adventures

2 Activity Options

Makai Adventures

Come experience all that West Maui has to offer with Makai Adventures on Kainalu, our 37' powerboat. Whether you want to go fishing, snorkeling or just cruise the coast, Kainalu will be able to get you there FAST!
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Kaha Loa

1 Activity Option

Make a reservation for the Kaha Loa

Kaha Loa is a 26-foot Glacier Bay power catamaran, perfect for cruising the waters around Lahaina and Maui. This boat features a shaded canopy top, an onboard marine head, fresh water shower, a full-feature stereo (feel free to bring your own music and we play it for you) a swim platform with ladder. There is plenty of seating on this boat, capable of carrying up to 10 guests, we only take a maximum of 6 guests in the interest of your comfort. The forward bow seating area is a very popular feature and this boat will reach speeds up to 28 knots, depending on ocean conditions.
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Sea Monkey

1 Activity Option

Sea Monkey -  a 32' sport yacht offering private tours

Sea Monkey is a perfect boat for a private charter of up to 6 for your family or special small group. Spend a day or watch the sunset on the water.
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Kainani Sails

2 Activity Options

Maui Sailing Charters

Private sailing charters aboard a 45' Beneteau Oceanis, Maui's newest monohull charter yacht. Come on board for an exclusive, personalized and memorable experience for up to 6 people. Sailing, snorkeling, wildlife, sunset cruises, sightseeing, celebrations, proposals, memorials and even elopements... anything is possible!
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Recent Reviews


Video Transcript

Well, this next short video segment is about sunset sails or sunset cruises on Maui.

If you're wondering what the difference is between a sunset cruise and a Dinner Cruise, you're correct if you assume that it was the dinner. That is basically it. These are two-hour sails or cruises. It could be a sailboat, or it could be just a boat without a sail that goes out cruising at sunset time. Dinner Cruises will include a dinner in the package. Sometimes they might be a little bit longer too. It might be two and a half hours, or they could be two hours. These sunset sails are typically two hours in length. They go out to see this, to see sunset. I don't know if you could see this, but the green flash is always a big part of the sunsets here on Maui. It's seen almost all the time. You try to find it in a place where the sun is going down over the water, not over an island. Then you can just get that green, green look, that green flash, that happens.

These are popular and they're fun. They're less expensive than the Dinner Cruises, but they get you out on the water. In many ways, I think of these as kind of something that you might do prior to going to dinner. You might do this at 5:00 and have a 8:00 dinner reservation, go out on the water, have a cocktail or two, have some hors d'oeuvres, watch the beautiful sunset, look back at the islands. Very, very relaxing. When you come in, you might then want to go over and have some dinner at a nice restaurant. They are in many cases like half the price of a dinner cruise, so it really just affords you the ability to get out on the water fairly inexpensively and have some drinks and enjoy your time out there.

We have them going out throughout the island, primarily from Lahaina and from Kaanapali and from Ma?alaea. The boats can vary from large cruising boats to Sailboats. Some we have that are actually smaller and a lot of privates we do on much smaller boats that you can take out for a two-hour period of time with just your group, that sort of thing. But in any event, the sunset sails are a good choice to enjoy the romance of Hawaii. If you have any questions about Tours or Activities in Hawaii, just give us a call or check out tombarefoot.com. We're here to help.


Taking a Hawaii sunset cruise may prove to be the most romantic and relaxing moments of your vacation. Sunset cruises probably won't rank high on your list of adventure items on your trip but may instead be the simple ending to a perfect day.

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Kauai is amazingly beautiful from on the island but it is ridiculously beautiful off the coast from the vantage point of a sunset sail.

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Oahu has plenty of these and they are a great value.

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A romantic sunset sail is one of the best ways to enjoy a sunset.

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