Sunset Cruises, Maui tours & activities, fun things to do in Maui

Sunset Cruises

Overall Rating

Sip on a tropical cocktail and feast on a delicious dinner on a variety of Hawaii sunset cruises and sails. Enjoy live music, hula shows, Friday night fireworks, and of course spectacular sunsets. Spend your evening on a cruise ship, powered or sailing catamaran, glass bottom boat, or even a pirate ship! These fun and relaxing sunset cruises are a must-do activity for anyone visiting Hawaii.

Dinner Cruises

Choose from a variety of Maui’s most popular sunset cruises departing from Lahaina, Kaanapali Beach and Maalaea Harbor. Whether you are looking for a fun evening with family and friends or if you are seeking a romantic evening experience to impress your special someone, we have the best Maui dinner cruise options. Enjoy a premium dining experience on the Calypso, Ocean Quest, Alii Nui and Trilogy. Or opt for a more casual dinner cruise with Pride of Maui, Maui Princess, Sea Maui and Quicksilver.
Sunset Cocktail Cruises

Enjoy tropical cocktails and live music, create picture perfect memories, and celebrate the aloha spirit on a Maui sunset cocktail cruise. Whether you are looking for a romantic experience or a fun evening with family and friends, we have the best sunset cruise options on Maui. Let the good times roll on a booze cruise with Sea Maui and Pride of Maui. Or relax on a casual sunset cruise with Quicksilver, Ocean Spirit and Trilogy. Book early as they sell out quickly!

12Activities

1/1 pages

Availability varies by date for all activities.

No.1

Top Seller

Maui Princess Sunset Dinner Cruise from Lahaina with Live Music and Cocktails
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Depart from Lahaina with Maui Princess on a premium sunset dinner cruise. Enjoy a relaxing cruise in Maui with live music & cocktails. Enjoy a 3-course dinner and panoramic views of Maui on this sunset cruise in Lahaina's beautiful ocean.

Meal Provided

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From USD117.11

23%
OFF

(72 reviews)

Daily

3 - 20 hour(s) (evening)
No.2

Sea Maui Kaanapali Sunset Cocktail Sail with Open Bar
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Set sail from Kaanapali beach along Maui's west coast, watching the sky break into an array of colors at sunset while enjoying open bar drinks & tasty appetizers. On Tue, Thu & Sat enjoy live music with local artists. The best booze cruise in Maui!

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From USD78.23

12%
OFF

(32 reviews)

Daily

(afternoon, evening)
No.3

Top Rated

Pride of Maui Sunset Luau Dinner Cruise with Open Bar & Polynesian Dance Show
TOP PICKS

Enjoy a luau dinner party aboard Pride of Maui, Maui's best sunset cruise! Featuring premium open bar, Polynesian dance, live music, delicious island cuisine, views of Maui’s scenic coastline and a spectacular sunset. Departs from Maalaea Harbor.

Pick-up Provided

Meal Provided

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USD102.88

(56 reviews)

Tue, Thu, Fri, Sat

2.5 - 5.5 hour(s) (evening)
Trilogy Maui Cocktail Sunset Sail with Premium Open Bar & Gourmet Tapas

Embark on a premier sunset cruise aboard a luxury sailing catamaran. Sit back and watch the sunset as you enjoy a premium open bar and delicious appetizers served by the friendly crew of Trilogy. Departing from Kaanapali Beach or Maalaea Harbor.

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From USD99.83

(13 reviews)

Daily

2.5 hour(s) (afternoon, evening)
Romantic Sunset Dinner Sail Cruise with Open Bar (from Maalaea & Lahaina Harbor)
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Sail along Maui's majestic Pali Sea Cliffs on a sunset evening cruise that includes a delicious gourmet dinner, open bar and a convenient Ma'alaea or Lahaina Harbor departure.

Meal Provided

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From USD151.43

(4 reviews)

Sun, Wed, Thu, Fri, Sat

3 hour(s) (afternoon, evening)
Calypso Cocktail Cruise - Maui's Most Affordable Sunset Cruise (Maalaea Harbor)
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Sink into tranquil relaxation as you cruise along side the legendary Pali-HWY. Featuring Maui's only triple Decker catamaran, giving you the best vantage point out of any boat in Maui to witness the breath taking Hawaiian sunset.

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USD55.94

5%
OFF

Family Discount

Sun, Mon, Wed, Fri

2.5 hour(s) (evening)
Ocean Spirit Maui Sunset Sail with Cocktail & Appetizers (from Lahaina Harbor)
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Disembark historic Lahaina Harbor on a relaxing sail as the sun sinks aboard Ocean Spirit, Maui's newest luxury sailing catamaran. Take in panoramic views of Maui as you enjoy premium appetizers and island cocktails served by the friendly crew.

Special

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USD89.16

(2 reviews)

Sun, Mon, Tue, Thu, Fri, Sat

3 hour(s) (afternoon, evening)
Island Rhythms Maui Sunset Cocktail Cruise with Live Music (Maalaea Harbor)
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Back by popular demand, Maui's very own Marty Dread brings live music and fun on a Hawaiian sunset sail that is fun for all ages. Get ready for a night filled with island-style reggae music and dancing, delicious appetizers, and refreshing cocktails!

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USD95.59

Family Discount

Fri

3.5 hour(s) (evening)
Calypso Maui Sunset Dinner Cruise with Cocktails & Live Music (Maalaea Harbor)
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Take in the sunset as you relax aboard this 2-hour dinner cruise that features a full 3-course meal, local live music and a 3rd deck for the best sunset views Maui has to offer. This is one of Maui's few cruises to offer lobster as a dinner choice!

Meal Provided

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From USD98.70

5%
OFF

Sun, Mon, Wed, Fri

2.5 hour(s) (evening)
Sea Maui Kaanapali Sunset Dinner Cruise with Open Bar
Quick Confirmation

Enjoy a 2.5 hour Open Bar dinner sail in Kaanapali featuring a full buffet served with your choice of chicken, fish, beef or veggie options prepared by a renowned local chef Joey Macadangdang. Whale watching included Jan through April!

Meal Provided

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From USD143.60

11%
OFF

(1 review)

Daily

(afternoon, evening)
Ocean Quest Lahaina Sunset Cruise with Four-Course Dinner & 3 Free Cocktails
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A uniquely Maui outdoor dining experience featuring a delicious chef-prepared four-course dinner served table-side by our attentive crew. All entrees are freshly grilled onboard during your cruise and all guests are guaranteed outdoor seating.

Meal Provided

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From USD104.12

Daily

3 hour(s) (evening)
Quicksilver Maui Sunset Dinner Cruise
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Quicksilver invites you for a cruise along the picturesque coastline of West Maui. This 2 hour Pacific Rim Cuisine Sunset Dinner Cruise featuring table-side service, local live music, great drink specials and unforgettable sunset views.

Meal Provided

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From USD89.95

10%
OFF

Tue, Thu, Sat

2.5 hour(s) (evening)