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 ankles and occasionally your knees.. when you board the vessel. Enjoy the panoramic views as you sail the trade winds between Maui, Molokai and Lanai.

On Paragon Lahaina Sunset Sail combine the adventure of performance sailing and the beauty of a golden Hawaiian sunset. This tour offers hot & cold hors d’oeuvres and beverages, including beer, wine, champagne & Mai Tais.

Departing from the downtown harbor of the historic whaling port of Lahaina, 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.

CMaui Sunset Cruisesruise Ship Passengers

NCL cruise ship passengers in Kahului are able to do some of these Maui Sunset Cruises but an hour drive is required. Lahaina cruise ship passengers are able to do these cruises as long as your ship is in port on one of the days that the cruise operates.


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. A short cab ride of about 10 minutes is required.


Cruise ship passengers are unable to do the Paragon Sunset Sail.

Activity Tips

Kevin Ditamore – Owner / Manager

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!

Occasionally 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 summer season there is a good chance that if there are just two of you, it is possible you’ll share a table with another couple. Might be a good chance to make new friends. 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. The dinner cruise is a more laid-back boating experience … the appetizer cruise does more tradewind sailing.

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.