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Sunset Sails & Cruises on Maui

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There are 33 tours in this category that range in price from $24.95 to $3500.00.

Sunset Sails & Cruises

Maui's coastline is lovely at any time of day, but even more beautiful during a Maui sunset sail.


From the deck of a Maui sailboat in the light sundown breeze, you will understand why sunset sails are so popular here on Maui.


The strong afternoon winds die down at sunset and are reduced to a gentle breeze.


The heat of the day has been replaced with a hint of coolness.


The bright wash of midday has turned to vivid pastels.


The sun glows orange and red and drops quickly into the ocean, disappearing in an instant display of Maui's famous "green flash."


The water is calm, a gentle swell lulls the quiet scene.


Looking back toward Maui, you find the West Maui Mountains or the slopes of Haleakala draped with rainbow colors and a halo of clouds turns from pink to purple to violet before your eyes.


And then a twinkling, a glitter, as stars appearing above the Lahaina or Kihei lights reflect across the water.


If you're lucky, as I was the first day I set foot on Maui many years ago, you may see the full moon rise out of an enchanted valley.


It's a good omen: you'll be back again as Maui now has you under its spell.


Many vessels can take you on a sunset cruise.


Most sunset sails depart from Lahaina and Maalaea Harbors.


Catamarans, sloops, schooners, and even power vessels are used for this purpose.


No matter what boat you take, one thing is certain.


It will be the beginning of an evening you will remember for a long time to come.


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.

Look for this symbol in the tour descriptions below to indicate if it is Pride of America compatible.


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Sunset Sails & Cruises Sorted by Specific Tour


We sell tickets to 33 items in the category Sunset Sails & Cruises on Maui.

View the complete list below or use our Activity Finder to narrow down your options.

Displaying 33 of 33 Results

$118.90

Alii Nui and her expert crew will treat you to a memorable evening! Go with them as they set the sails and chase the sun as it sets into the distant horizon into the Pacific Ocean. Enjoy a delicious array…

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$152.90

Come aboard the Ali'i Nui catamaran and experience a dinner like no other on Maui. The Royal Feast provides a unique dining experience while you relax in comfort and dine like royalty. This two and…

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$46.89 - $70.89

Come aboard the Calypso, Maui's brand new catamaran, and enjoy a sunset dinner cruise along the south Maui shoreline. Upon leaving Maalaea Harbor relax as you cruise the coast and listen to live music,…

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$24.95 - $38.89

Calypso Sunset Cruise is a two hour sunset cocktail cruise along the Maui coast! This tour is a great option for adults who want to enjoy the sunset on the ocean but not have a full dinner. Guests will…

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$70.90

Set out from Ka'anapali Beach aboard the 64' catamaran "Gemini". See the beautiful Hawaiian sunset as well as the tri-island view of Maui, Molokai and Lanai (and if you look to the South you can even see…

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$84.90

Enjoy 2.5 hour sunset dinner cruise on board Maui Princess offering topside dinner seating and stunning scenic views. Guests dine on linen covered tables with full table side service by wait staff. A live…

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$81.90

Come experience a traditional Hawaiian Outrigger Canoe Tour as you learn the art and sport of canoe paddling and information pertaining to the non-instrumental navigational techniques used by Polynesian…

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$83.00

During the summer on Maui from April to December the Hula Girl 3 Hour Sunset Dinner Cruise returns. The background music is a soothing compilation of Hawaiian and Island style tunes over a state of the…

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$1600.00

Choose the one of a kind beautiful sailing catamaran "Hula Girl" for your next private-charter excursion. Different seasons boast special attractions but all year Maui has wonderful things to see and experience…

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$70.00

Select the 2 Hour Sunset Sail with a focus of high tech sailing in West Maui's tradewinds with a no-host appetizer menu that likens any local restaurant. Hula Girl is decked out with Spectra racing…

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$700.00

Your Private Charter is designed to fit your perfect Maui vacation experience. Aboard the Kaha Loa you can go snorkeling, go on the search for whales and dolphins, cast some fishing lines out for the area's…

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$825.00

Set sail in the calm leeward waters of Lahaina and discover the beauty of catching the wind. Relax and enjoy 360 degree views as the sun sets and lights up the islands of Maui, Molokai and Lanai. A private…

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$899.99 - $2359.99

Guests can book a private adventure on the 37' Kainalu powerboat for groups up to 24 for options like snorkeling, whale watching, dolphin tours, at sea memorials, bottom fishing or just to catch the sunset!…

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$135.00

Book the Sunset Champagne Cruise to enjoy a two hour sunset sail departing from a beautiful white sand beach in South Maui. Sample the Pupu "Appetizer" Buffet and sip on beverages or cocktails from the…

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$109.00 - $650.00

Enjoy a private sunset on the water or opt for a shared boat with other visiting guests. Shadowfax is a blue water sailer and you will enjoy a beautiful Maui sunset under sail. Hot and cold appetizers will be offered for your enjoyment.

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$76.89 - $94.89

Enjoy a premier dining experience on the waters of Maui. All guests are offered outdoor seating, and indoor by request. Departing nightly from historic Lahaina Harbor, this cruise features a stunning sunset…

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$52.89

Join Pacific Whale Foundation for a celestial stargazing cruise, featuring special guest astronomer Harriett Witt. Cruise beneath a starlit sky and learn about the stars, tides and cultural significance…

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$59.89

What could be more fun than dancing on the bow of a boat to live island-style music and pop/rock favorites by Maui recording artist Eric Gilliom. This open-air dance party at sea is a great multi-generational…

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$59.89

What could be more fun than dancing on the bow of a boat to live island-style music and pop/rock favorites by Maui recording artist Eric Gilliom. This open-air dance party at sea is a great multi-generational…

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$66.89

On this adults- only (21 and over) cruise, experience the essence of ho'okipa (hospitality) as we share with you the breathtaking beauty of Maui's sunset. Departing from historic Lahaina Harbor, you'll…

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$57.89

Experience the essence of ho'okipa (hospitality) as you the breathtaking beauty of Maui's sunset. Departing from historic Lahaina Harbor, you'll experience the beauty of the Pacific Ocean while island…

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$68.90

The peaceful sounds of the wind in our sails while viewing Maui's Western coastline offers a most relaxing experience. The crew will pamper you with complimentary hors d'oeuvres and beverages including beer, wine, champagne and Mai Tai's!

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$68.90

Take a scenic cruise off the shores of Maui for sunset viewing, gourmet appetizers, open bar and great entertainment. Live entertainment is provided by master guitarist Joe Cano. He performs solo on Tuesday…

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$450.00 - $3175.00

This wonderful Power Flybridge catamaran is an ideal private charter boat for small groups or a family searching for a moderately priced excursion with the luxury of a private charter. Go sailing, snorkeling,…

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$61.90

Enjoy two hours of sailing off the majestic West Maui Coast, and enjoy a beautiful sunset at sea while you sit back, relax and let us do all the work. Whale watching when in season, December-May.

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$1200.00 - $2100.00

Design your own custom charter for you and your private group.

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$61.90 - $3500.00

Sunsets at sea, a premier sailing experience! Each night is different and unique. While you take in views of Molokai, Lanai, Maui and Kahoolawe Chef Joey will delight you with appetizers "pupus" prepared…

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$71.90 - $3500.00

Live Entertainment and a sunset at sea, a most unique Maui sailing experience! Choose from two different wonderful performers, Tuesday Daesha Dee and on Thursday Bradda Francis. Take in views of Molokai,…

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$770.00

Plunge into the most exclusive and romantic way to watch sunset in Maui! The unobstructed views of sunset paired with warm tropical air and world-class service provided by Sea Monkey Staff will insure…

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$58.90

Come and enjoy a wonderful two hour sunset sail with appetizers and an open bar, departing from West Maui's beautiful Ka'anapali area.

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$76.90

Enjoy two and a half hours on the ocean for a Maui sunset sail, savor dinner and a drink from the open bar.

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$88.26

Experience a idyllic sunset sail exploring the West Maui coastline surrounding Kaanapali. Enjoy Maui's legendary kamakani (wind) with Trilogy. They really put the sails up then while you take it all in…

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$132.84 - $132.84

Experience fine dining with an unbeatable view! Tables are set for intimacy and comfort. Your evening begins with cocktails and sailing along the pali sea cliffs. After mooring in a protected cove, your…

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Sunset Sails & Cruises Sorted by Company

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(3 Reviews, 5 Stars)

Hula Girl

3 Activity Options

65' Sailing Catamaran

You would be 'hard pressed' to find a more beautiful sailboat on Maui to take out on a snorkel sail, whale watch, dinner or sunset sail or a private charter. This multimillion dollar state of the art 65'x35', 90' wing mast sailing catamaran is designed for sailing and for maximum comfort. In addition it comes with its own full galley and private chef so all your meals will be prepared custom just for you.
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(3 Reviews, 5 Stars)

Trilogy Excursions

2 Activity Options

64' - 55' - 51' Sailing Catamarans, 55' Sailing Catamaran, 55' Catamaran to Molokini, 55' Sail Catam

One of the most popular and respected boating companies on Maui is the Trilogy which has been in operation here since 1973. Though being a large company now, operating six or so 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 Lanai, Molokini, the West Coast of Maui and an assortment of shorter sunset and sailing options and whale watches.
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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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(2 Reviews, 5 Stars)

Frogman Charters

2 Activity Options

55' Power Catamaran

The charter boat company Boss Frog's is also known by the name Frogman Charters and it operates Molokini tours, whale watches, sunset sails and dinner cruises from it departure point of Maalaea Harbor. It's two main boats are the 55' power catamaran Malolo and the 55' power catamaran Quicksilver.
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(1 Review, 5 Stars)

Kainani Maui Sailing Charters

2 Activity Options

Kainani Maui Sailing Charters

Her modern yacht shape, spacious interior, and blue water sailing capabilities make her the perfect Hawaii sailing charter boat. She is also available for Memorials at Sea or Ash Scattering Services and special requests.
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(1 Review, 5 Stars)

Hawaiian Outrigger Experience

1 Activity Option

Book the Hawaiian Outrigger Experience.

Experience and relive a part of Hawaiian History as your cultural guides teach you traditional chants (oli), ancient myths, legends and historical facts. In honoring the wisdom and knowledge passed on by generations from ancestors. Offered daily Hawaiian Outrigger Canoe Tours depart from Wailea Beach in South Maui.
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(17 Reviews, 4.9 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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(12 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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(6 Reviews, 4.8 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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(29 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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(4 Reviews, 4.8 Stars)

Sea Maui

2 Activity Options

Make reservations for a snorkel trip or sunset sail on the Sea Maui.

Sea Maui is a beautiful 51 foot power, sailing catamaran that departs out of Kaanapali Beach. They offer a trade-wind sail every afternoon, a sunset sail in the evening and snorkel trips in the morning. Food is specially provided by renowned Chef Joey Macadangdang the former corporate executive chef of Roy's Kitchen.
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(31 Reviews, 4.6 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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(7 Reviews, 4.6 Stars)

Paragon Sailing Charters

1 Activity Option

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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(8 Reviews, 4.1 Stars)

Pacific Whale Foundation

6 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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(2 Reviews, 4 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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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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Privacy Charters

1 Activity Option

Sailing, Power Catamaran

Privacy features a large air conditioned cabin with a couch seating for 3 guests, table seating for four, or sit in either of the two captains chairs at the lower helm station. Further forward there is a large clean restroom on the port side, and stateroom with a queen size bed on starboard side.
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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 -  is a 31 foot Sea Ray Sundancer  Yacht

Sea Monkey is perfect for a private charter of up to 6 of your favorite people for a day or sunset on the water.
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Top Activities
Customer Favorite Tours Based on Reviews

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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A Kauai sunset sail or Kauai sunset cruise is a good call for any evening of your vacation but perhaps the very best time would be your last evening on the island for a fond farewell.

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A variation of the dinner sunset cruise is what is fondly referred to in Hawaii as the "booze cruise". This usually includes just "pupus" (appetizers) and an open bar plus entertainment.

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Sunset Sails off the coast of the Big Island of Hawaii provide the ultimate in relaxation. The beauty of the ocean and the colors of the sunset provide a remarkable experience to conclude your Hawaiian day.

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