Sailing Cruises

What’s the best sailing cruise Maui visitors can go on?

Whether you’re planning on spending the day on the water looking for whales, dolphins, turtles, or joining one of Maui’s beautiful sunset cruises, sailing trips are one of the best ways to do it. Instead of a roaring engine, picture yourself gliding through the Pacific Ocean on a sailing sunset dinner cruise with your family and friends. How do you choose between all the options to make sure you’re getting the best sunset cruise Maui can provide? Read through our favorite trips below and let us know if we can help you pick the right sailing trip.

Sail Maui

Known as the premier sailing catamaran company on Maui, Sail Maui offers snorkeling trips to Lanai and Molokini, nightly sunset sails, and for those with a large group or wanting more privacy, they offer private charters on their roomy, beautiful sailing catamarans. For over 25 years, Sail Maui has brought joy and excitement to Maui visitors from around the world.

One of their best sunset dinner cruises is the Paragon Performance Sunset Sail, which includes hot and cold pupus (appetizers), beverages (beer, wine, mai tais, and champagne), and beautiful views of the Maui sunset.

Join a trip on the Paragon, Paragon II, or the new ‘Alihilani catamaran for an unforgettable sailing experience. Departing daily from Lahaina and Maalaea Harbors. The crew suggests casual attire and a light jacket for sunset sails.


If you’re looking for adventure, search no further than the Teralani. With options for all-day and half-day snorkel trips to Lanai and Maui’s West side, whale watches, and sunset dinner cruises, you can fit a Teralani trip into your itinerary with no problem.


Looking for a snorkel or SNUBA escapade? The luxurious Trilogy sailing catamaran offers a 5.5-hour trip to discover Molokini (some of the clearest water you’ll ever snorkel in), an 8-hour trip to discover Lanai, a 5-hour discover Kaanapali journey exploring the protected bays of Maui’s West coast, a 4-hour discover Olowalu trip to see ancient corals on Maui’s “mother reef”, and for those who prefer to adventure with their taste buds, a 2.5 hour Captain’s Sunset Dinner Sail, one of the most popular sunset dinner cruises on the island.

If you came to Maui to witness whale season, the Trilogy boat offers 2-hour whale watching tours from Lahaina, Maalaea, and Kaanapali, where you’re bound to see whales and possibly other sea life, like dolphins, honu (sea turtles), and more! Contact us today to find availability for you and your friends, family, or partner to make your Maui vacation one you won’t soon forget.

Island Star and Scarab Powerboat

This 57-foot sailing Columbia Yacht, the Island Star, can hold up to 20 people and is used exclusively for private charters, so there are no individual tickets available for snorkeling or sunset dinner cruises. The boat can sleep up to 10 people, so it’s great for overnight trips to surrounding islands. An added option is to have a Miami Vice reminiscent scarab power boat tag along for exploring detailed coastlines and inlets around the Hawaiian islands. This is a great option for a group of people that want the freedom to explore the Hawaiian islands by water. Food and beverages can be added on for an additional cost.

Scotch Mist Sailing Charters

For a peaceful morning snorkel, a morning or afternoon adventure sail, or champagne sunset sail, Scotch Mist Sailing Charters is the choice for you. Holding up to 22 passengers, this intimate and sleek way to travel through Maui’s open waters is a breathtaking choice for a sailing journey. There’s nothing like gliding silently and quickly through the ocean water, guided by Maui’s wind and taking in the beautiful sight of the surrounding islands. This sailing boat is also available for private charter trips.

Snorkel and whale watch tours on the Scotch Mist can include sights of Spinner or Bottlenose dolphins, honu (sea turtles), and other wonders of the Maui waters. The champagne sunset sail is know to be the best sunset cruise Maui visitors can find—a lovely 2-hour tour, including complimentary champagne, a drink from the bar, and a colorful sunset. The sunset tour is limited to passengers 13 years of age and older.

Boarding is at Lahaina Harbor in the front row at Slip 2 on Maui’s beautiful West side.

Sea Maui

Maui boasts some of the most breathtaking sunsets in the world. What better way to enjoy one than with a sunset sail with live music, pupus (appetizers) from Executive Chef Joey Macadangdang of Joey’s Kitchen, an open bar serving premium beverages, and the possibility of seeing whales during whale season. With 360-degree views around the open layout of the sailboat, you won’t miss out on dolphin and whale sightings and can enjoy the vivid colors of a Maui sunset.

If you’re looking for a full dinner experience, join the premium sunset sail with dinner for a 2.5 hour cruise on the Sea Maui III, a 65-foot sailing catamaran. Enjoy live music, excellent food, and stunning views of the water, islands, and wildlife. This is one of the sunset dinner cruises you don’t want to miss.

Sea Maui is known as the best sunset cruise Maui visitors can find. On one of Sea Maui’s 2-hour sunset dinner cruises, you can see the surrounding islands of Kahoolawe, Molokai, Lanai and Maui. Sea Maui runs 2-hour sunset sails every day of the week out of Kaanapali.

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