Maui Sunset Dinner Cruises

COVID-19 UPDATE: All tour operators are adjusting their offerings to account for Covid-19 by reducing capacity and adjusting food and beverage service procedures. Of the tours on this page, the Maui Princess Dinner Cruise, Teralani Sunset Dinner Cruise, Teralani Holoholo Cocktail Sail and the Paragon Sunset Cruise are both operating now. The Pride of Maui Dinner Cruise will not be available until summer of 2021.

Teralani Sailing - Kaanapali

Teralani Sunset Dinner Sail and Holoholo Cocktail Sail has resumed operations and we are NOW accepting reservations for any future dates!


Teralani Sailing Charters offers two different daily sunset cruise experiences from Kaanapali Beach. Both Teralani 2 and Teralani 3 are beautiful 65' sailing catamarans. Both boats depart from Kaanapali Beach; guests take off their shoes and walk through the sand. You will likely get your feet wet (and maybe your ankels and occassionally your knees) when you board the vessel

Dinner Sunset Sail - Teralani II - 2.5 hours

Teralani's Dinner sail offers true sit-down-at-a table seating on a spacious and comfortable sailing catamaran. Current menu includes Fresh Chips and Fresh Pineapple Salsa, Asian Slaw, Chipotle Citrus Herbed Roasted Chicken, Roasted Molokai Sweet Potato, Garlic butter, Vegan Pita Wrap, and Sliced Fresh Baked Bread with Butter Pats. Dessert is Fudge Brownie Bites and Fresh Pineapple with torched cinnamon. Beverages include a full open bar with wine, champagne, micro-brewed beer on tap, Mai Tais, vodka, gin, and rum mixers, assorted soft drinks and tropical juices, etc.  Departure varies seasonally; typically the cruise runs from 4:30pm to 7:00pm in the summer and 3:30pm to 6pm in the winter. 

Teralani Dinner Sail Rate

$124.00 per Adult, $124.00 per Teen (13-20), $124.00 per Child (3-12), $124.00 per Infants (under 3)
(plus 7.167% Hawaii sales/harbor tax)

Teralani Holoholo Cocktail Sail - Teralani III - 2 hours

Teralani's original sunset sail includes appetizers and snacks and a full open bar. The menu includes assorted cheeses and crackers, chips and pretzels, pineapple teriyaki meatballs, spinach rolls, spring rolls, antipasto platter, and vegetable crudite. Beverages include a full open bar with wine, champagne, micro-brewed beer on tap, Mai Tais, vodka, gin, and rum mixers, assorted soft drinks and tropical juices, etc. Departure varies seasonally; typically the cruise runs from 5:00pm to 7:00pm in the summer and 4:00pm to 6:00pm in the winter. 

Teralani Holoholo Cocktail Sail Rate

$94.00 per Adult, $94.00 per Teen (13-20), $70.00 per Child (3-12), $55.00 per Infants (under 3)
(plus 7.167% Hawaii sales/harbor tax)


Cruise Ship Clients

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NCL Pride of America cruise ship passengers who come into Kahului are able to do Teralani sunset cruises but it does require a rental car as the drive to Lahaina takes a little under an hour. For rental cars with cruise ship shuttle pick-up see our rental car page.

Lahaina cruise ship passengers can do this tour on their first day in port with a short cab ride to Kaanapali as long as your tenders are running until 8pm.

Paragon Lahaina Sunset Sail

Paragon's Sunset Sails have resumed and we are NOW accepting reservations for any future dates!

Paragon Lahaina Sunset Sail Rate

$85.00 per Adult, $42.50 per Child (3-12), Infants (under 3) FREE
(plus 7.5269% Hawaii sales/harbor tax)

Experience high performance sailing and golden sunsets with Maui's premier sailing company, Paragon. They are equipped with twin vessels, Paragon & Paragon II, that feature new construction and hull design. The mast technology is the same as America's Cup winning catamaran, which allows for incredible speeds plus comfort and safety. Paragon has been dedicated for over 20 years to customer service for locals and visitors alike. Their experienced crew of friendly sailors create an exhilarating ride you'll never forget!

This 2 hour sunset sail is daily except Sunday, and the departure times are adjusted to seasonal sunset patterns. Check in is at Lahaina Harbor, public loading dock, in front of the Pioneer Inn. Check in from September 15th to November 14th is at 4:45pm, November 15th to February 14th is at 4:30pm, February 15th to May 14th is at 4:45pm and May 15th to September 14th is at 5:00pm. This tour offers hot & cold hors d'oeuvres and beverages, including beer, wine, champagne & Mai Tais. During whale season (December - May), witness the majestic humpback whales play with the Hawaiian sun setting across the ocean.

Paragon does not allow spray-on sunscreen, because it can go everywhere on the deck making it dangerous to maneuver around. They offer reef-safe sunscreen on their vessels. Bring a lgiht jacket, sunglasses, camera, reuseable water bottle, hat, and a towel. Paragon has a small inventory of towels available for purchase onboard. Bring a hat, sunglasses, camera, reusable water bottle, and towels.

Note: Their catering companies do offer vegetarian or gluten free options, but they cannot guarantee there no cross contamination for those with celiac disease or severe nut allergies.


Cruise Ship Clients

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Pride of America cruise ship passengers cannot do the Lahaina Sunset Sail as they are in port on Sunday evenings and this tour is not offered on Suudays.

Cruise ships that are in port in Lahaina may do this sunset cruise if your ship is overnighting, or if the last tenders back to your ship are offered until 8pm.

Maui Princess Dinner Cruise

Maui Princess dinner cruise is running Monday, Wednesday, Friday and Saturday evenings

Maui Princess Dinner Cruise Rate

$129.95 per Adult, $89.95 per Child (12 and under), $20.00 per Seat Covid Surcharge
(Hawaii sales tax included)

Maui Princess Dinner Cruise - Holiday Rate

$159.95 per Adult, $105.95 per Child (12 and under), $20.00 per Seat Covid Surcharge
(Hawaii sales tax included)

The Maui Princess has a special menu and higher rate for the following dates / events: New Year's Day, Valentine's Day, St. Patricks Day, Easter, Mother's Day, Memorial Day Weekend, Father's Day, 4th of July, Labor Day Weekend, Thanksgiving, Christmas Day, and New Year's Eve.

Maui Princess has added a $20 per seat Covid surcharge to account for operating at reduced capacity to allow for social distancing on the boat. The Maui Princess rates quoted above includes tax.

Departing from the downtown harbor of the historic whaling port of Lahaina, The Maui Princess is the largest and most stable vessel to make its home here in Maui's waters. This is a true dinner cruise ... including full table service for drinks, salad course, entree, and dessert served at your table by attentive staff in classy waiter attire. Dinner is served on the open air upper deck with panoramic views of the West Maui Mountains and the islands of Lanai and Molokai. Dinner includes your choice of prime rib, macademia nut mahi mahi, or 1/2 of a roast chicken ... they also have a vegetarian selection as well. The boat also features a bar for beer, wine, Mai Tais and other cocktails, and three drinks are included per person (additional drinks may be purchased for $3-5 each). Ater dinner live music and dancing is featured in the main cabin downstairs, or just hang out at your table and watch the stars appear.

Booking early is your best chance to score a table along the rail, so we recommend that you make reservations well in advance of your arrival on Maui! Tables on the Maui Princess seat four. Larger parties will be seated at adjacent tables, and parties of 8 or more have a $10pp service charge added that is paid at checkin.

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Cruise Ship Clients

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NCL cruise ship passengers in Kahului are not able to do the Maui Princess dinner cruise because it does not operate on Sunday evenings.

Lahaina cruise ship passengers can do this dinner cruise as long as your ship operates tenders until at least 9pm. No transportation is required as this ship leaves from the same harbor where your cruise ship tender arrives.


Kevin at Falls

Watching a sunset from the deck of a boat is a completely different experience than watching from the beach. Sunsets are three dimensional ... and there is no better way to realize the 360 degree view than to get out on the water. Not only does the sky turn different shades of pink and orange, the mountains are painted with this colorful brush as well. Get out on the water and REALLY enjoy a sunset!

Occassionally I've heard clients say "We could have gotten a nicer meal for the same money in a restaurant." I think that's stating the obvious ... you aren't just paying for a meal on a dinner cruise ... you are paying to go out on a boat, and as a boat owner I can tell you that they are EXPENSIVE to operate and maintain. If you don't get your expectations too unrealistically high you'll have a great time.

The most popular and longest-running sunset cruise is the Maui Princess dinner cruise. My wife and I recently took two friends of ours out on this vessel ... it had been a while since we had evaluated this cruise. We purposely ordered three different entrees and are pleased to report that all around the food was a winner! The prime rib is sliced on board, and the cut was generous and of high quality. The mahi mahi and chicken entrees were equally tasty and highly recommended. We didn't try the vegetarian entree, but the fact that they HAVE a vegetarian entree is a good sign! It is obvious that this tour operator is really trying hard to provide a quality product. Also a nice new feature ... the Maui Princess is able to board passengers at the main loading dock of Lahaina Harbor; gone are the days when you had to ride a shuttle boat out to board offshore! Tables on this boat seat four; during busy times of the year when the boat is reasonable full there is a good chance that if there are just two of you, it is possible you'll share a table with another couple. It's a good chance to make new friends and share vacation experiences from around the world. It's also nice to have someone to whom you can hand your camera for a photo.

For guests staying at Kaanapali we recommend one of the beautiful sailing catamarans that leaves right from the beach. Teralani Sailing offers two different boats ... one with a full dinner cruise and one with appetizers. Of the two, the dinner cruise is the more "laid-back" boating experience and the appetizer cruise is a more exciting, wind-blown "tradewind sailing" excursion.

If you are coming to Hawaii from December through April months, there is the added bonus of humpback whale sightings on sunset cruises. All boats will be going out of their way to find whales for you during these months.