Sunset Sail in Maui: A Dinner Cruise You’ll Never Forget!

Romantic, relaxing, and pretty much unforgettable, a Maui sunset cruise is an exceptional way to spend a Maui evening.

These special cruises float through the waters of Maui as you watch a golden sunset, often with a cocktail and an appetizer in hand.

To book the best Maui sunset dinner sail, or sunset cocktail sail, check out this guide.

Small yacht in the ocean at sunset.

Best Maui Sunset Cruises

Trilogy Deluxe Ka’anapali Sunset Sail

The convenient Trilogy Deluxe Ka’anapali Sunset Sail departs directly from Ka’anapali beach, and gives you a chance to get away from the resort crowds.

Premium signature cocktails can be enjoyed from private tables, along with plated appetizers made from local ingredients.

Couples will find this sail is a romantic and intimate 2-hour journey against the Maui sunset.

Pride of Maui Sunset Luau Dinner Cruise

Struggling to find time for a sunset cruise AND a Maui luau?

The Pride of Maui Sunset Luau Dinner Cruise combines them both. This is a really unique experience, with dinner paired with Polynesian dancers and the epic Maui sunsets.

An unforgettable family evening, the Pride of Maui departs from Ma’alaea Harbor, and the journey lasts for 2 hours.

Kai Kanani Adventure Sunset Sail

Sunset on the Kai Kanani Adventure Sunset Sail is celebrated with a Lokelani Sparkling Rosé toast. Live music and three courses of appetizers make this a family-friendly cruise with a vibrant atmosphere.

There’s also a well stocked open bar, featuring many local favorites. This is the only catamaran tour on South Maui, and check-in is at Maluaka Beach. 

Sea Maui Premium Sunset Cruise With Dinner

The Sea Maui Premium Sunset Cruise With Dinner takes you aboard a 65-foot luxury catamaran, as you explore the Maui ocean. Enjoy a hearty menu packed with local flavors as you take in the sunset from the cozy deck tabletops.

Or relax with a cocktail in the spacious cabin. Check-in is at the Whalers Village in Ka’anapali, and the cruise takes 2.5 hours.

Sea Maui also offers a Sunset Cocktail Cruise, and a Sunset Live Music Cruise.

Pacific Whale Sunset And Celestial Cruise

When most sunset sails are heading back to harbor, the Pacific Whale Sunset and Celestial Cruise is just getting started.

With Pacific Whale, you can watch the sunset, and then get a guided tour of the night sky.

Educational and fun, the cruise includes appetizers and drinks alongside the Hawaiian cultural journey. PacWhale also offers a Sunset Cocktail Cruise from Ma’alaea.

Quicksilver Lahaina Sunset Dinner Cruise

Tuck in on the Quicksilver Lahaina Sunset Dinner Cruise, a sunset sail that comes with a packed full menu.

Enjoy local specialties such as Hawaiian slow roasted prime rib, or the local island fish, with a complimentary cocktail (or two).

The friendly crew and island music make this a dinner cruise ideal for friends and families. Departing from Lahaina Harbor, the cruise lasts for 2 hours.

Sail Maui Lahaina Sunset Sail

The delightful Paragon Performance takes you out on the Sail Maui Lahaina Sunset Sail.

This is an exhilarating sunset cruise, particularly if the wind picks up, as the Paragon is a nifty vessel.

Nibble on hot and cold pupus, and sip on Mai Tais and champagne as the sun slips down the Maui sky. The Sail Maui cruise departs from Lahaina Harbor daily, and lasts for around 2 hours.

Alii Nui Sunset Dinner Sail

For a real touch of luxury, the Alii Nui Sunset Dinner Sail is an exclusive Maui sunset cruise experience.

With limited guest numbers, sailors can stretch out in comfort with a glass of wine and an impressive buffet.

And you really can enjoy the bar, as the Alii Nui complimentary transport will return you to your hotel once the sun has set. 

What Is A Maui Sunset Sail?

The golden sunset is an icon of Maui, with amateur and professional photographers seeking out the best place to capture it.

A Maui sunset sail offers you one of the most exceptional views you can ask for.

Departing in the late afternoon, a sunset sail tours the coastline as the sun sinks down the sky, before returning to land after dark. Romantic, atmospheric, and completely unforgettable.

Two sailboats at sunset.

Dinner Cruise Or Cocktail Cruise?

Toasting the sunset with a cocktail or glass of wine is fairly standard on most Maui sunset sails, but there are a few options to choose from. Most sunset sails operate either as a dinner cruise or a cocktail cruise.

Dinner cruises treat you to the full meal. Diners pick from a limited menu, and food is served to the table. An open bar is generally included. Dinner cruises are typically the more expensive option.

A cocktail cruise might not serve a full meal, but you do have access to well stocked bars. And most sails have appetizers and pupus on hand to soak up the booze. Cocktail cruises are better if you’re on a tighter budget.

Cruise companies will add their own twist to make their tour stand out. Look for live music, dancing, and even cultural talks as additions to the standard sunset sail. 

Choosing Your Departure Destination

Sunset sails typically depart from West or South Maui. Remember, they do get back after dark, so consider a departure point close to your accommodation.

Cruises leave from either the beach or the harbor. For a beach departure, the boat pulls up onto the sand, so expect to get your feet wet. If you want to stay dry, look for a harbor departure. 

Do You Need To Book A Maui Sunset Sail In Advance?

It’s typically better to book your sunset sail ahead of time, because spaces can fill up.

The boats are fairly small, and a sunset sail is one of Maui’s most popular activities. But you can get lucky—sometimes a company will have spare spaces right before departure. 

Maui Sunset Sail

Toasting the Maui sunset from the deck of a boat is the sort of experience you never forget.

Book a sunset sail to experience the magic of the golden Maui sunset, alongside some of the best foods and flavors the island has to offer. 

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