Maui Sunset Dinner Cruises


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 (subject to change) includes an Antipasto Bowl (Assorted Cold Cuts, Olives, Pesto Marinated Assorted Vegetables, Fresh Mozzarella Cheese and drizzled with Olive Oil & Italian Seasoning), Mediterranean Salad, Ginger Teriyaki Chicken with Stir-fried Vegetables and Ginger Infused Jasmine Rice. Dessert is Maui Gold Pineapple Dipped in Dark Chocolate and OPEN BAR INCLUDES: "Teralani Sunset Cocktail", White Wine, Sparkling Rose, Beer on tap, Mai Tai, Vodka, Rum and Mixers, Assorted Soft Drinks, Tropical Juices and Water. Departure time 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

$140.16 per Adult (13+), $110.16 per Child (6-12), $110.16 per Infants (under 6)
(plus 7.712% Hawaii sales/harbor tax)


Teralani Holoholo Cocktail Sail - Teralani III - 2 hours

Teralani's Holoholo Cocktail sunset sail includes appetizers and snacks and a full open bar. The menu includes Caprese Skewers (Pesto Marinated Cherry Tomatoes, Olives & Fresh Mozzarella Cheese and drizzled with Aged Balsamic Glaze), Traditional Shrimp Cocktail, Turkey Pesto Wrap and Maui Gold Pineapple Dipped in Dark Chocolate. OPEN BAR INCLUDES: "Teralani Sunset Cocktail", White Wine, Sparkling Rose, Beer on tap, Mai Tai, Vodka, Rum and Mixers Assorted Soft Drinks, Tropical Juices and Water. Departure time 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

$110.16 per Adult, $100.16 per Child (6-12), $70.16 per Infants (under 6)
(plus 7.712% Hawaii sales/harbor tax)

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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!

Experience high performance sailing and golden sunsets with Maui's premier sailing company, Paragon. Their fleet of new sailing catamarans 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!

Paragon offers two different sunset sailing experiences out of Lahaina Harbor on two different boats. Both vessels are the same cost and both offer hot & cold hors d'oeuvres and beverages, including local beer, wine, champagne & Mai Tais. Both are offered daily with checkin time adjusted seasonally to the sunset. Your confirmation email will give you the exact time for checkin and departure.

Paragon Lahaina Performance Sunset Sail Rate

$105.00 per Adult, $74.00 per Child (3-12), Infants (under 3) FREE
(plus 8.108% Hawaii sales/harbor tax)

The 2 hour Paragon Lahaina Performance Sunset Sail is done on a smaller 45 foot catamaran and is a more exhilirating sailing experience. This means there will also be more salt spary and the cruise will be somewhat rougher. It is a little harder to eat and drink on this performance sail, but offers a greater level of intensity in the sailing experience. The Performance sail is limited to just 20 guests.

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Paragon Alihilani Sunset Sail Rate

$105.00 per Adult, $74.00 per Child (3-12), Infants (under 3) FREE
(plus 8.108% Hawaii sales/harbor tax)

The 2.5 hour Paragon Alihilani Sunset Sail is done on a larger, more luxurious 45 foot catamaran and is a more relaxing sailing experience. The sailing speed is more conducive to eating and drinking and offering laid-back sunset views. The Alihilani is a more spacious vessel but capacity is limited to 45 guests.

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Note: Paragon's catering company does offer vegetarian or gluten free options, but they cannot guarantee there is 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 Lahaina Sunset Sails but a rental car is required as the drive to Lahaina is about an hour.

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 operating 7 days a week

Maui Princess Dinner Cruise Rate

$139.26 per Adult, $96.40 per Child (12 and under), $20.00 per Seat Covid Surcharge
(Hawaii sales tax included)

Maui Princess Dinner Cruise - Holiday Rate

$171.41 per Adult, $113.54 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 certain holiday dates. The only current holiday rate on the schedule is Fourth of July 2023.

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. A "Welcome Mai Tai" and one alcoholic beverage of your choice is included per person (additional drinks may be purchased for $4-6 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 $15pp 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.


ACTIVITY TIPS

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.