Top Maui Cruises & Sailing

Enjoy a ‘front-row seat’ for Maui’s epic sunset accompanied by handcrafted cocktails and snacks during this sailing cruise from Kaanapali Beach. Enjoy views of nearby Lanai, Molokai, and Kahoolawe from your boat, cocktail and food in hand, as the Hawaiian sky puts on its nightly display. Snacks, unlimited alcoholic drinks, and non-alcoholic beverages are all included.

Hawaii is a major destination for relaxation and fun times—and this Maui sunset dinner cruise allows you to let loose and enjoy yourself while visiting the island. Step aboard a ship that cruises by the Na Pali coast, and take in views during sunset as you feast on your dinner of choice. Dance to live music, sip on two free drinks from a full bar, and create your own memorable experience on the water.

Set sail into the sunset aboard a retired racing yacht with this cruise. You'll hop aboard the Sunset Mist in Lahaiana and sail out into the Pacific, where you'll have your choice of beer, wine, or soft drinks. Best of all, group sizes are capped at 22 people so you won't have to worry about crowds.

Leave behind the crowds of Ka’anapali Beach and spend the evening on a sunset dinner cruise off the coast of Maui. The perfect romantic evening out, this sunset cruise offers unmatched island views, photo opportunities, and even the chance to spot whales (December–April). Plus, the buffet dinner comes with handcrafted cocktails and premium beers.

Watch the Hawaii sunset aboard a sailing catamaran while listening to live music for a fun twist on the conventional sunset cruise. Depart from Kaanapali Beach and soak in great views of Maui as popular local performers play traditional, contemporary, and reggae versions of favorite songs. Your sailing cruise includes an open bar with drinks and 'pupus' (appetizers).

Board the beautiful and spacious Pride of Maui catamaran for a sunset cruise near the Molokini crater. Enjoy an open bar including craft beer and blended drinks, plus a generous buffet featuring barbecued ribs, honey-glazed chicken, stir fried vegetables, and more. Watch the sun set, take in a live hula show and if you’re lucky, you may even see humpback whales during mating season.

Catch an exciting peek at the underwater world on this whale-watching cruise in Maui. Your excursion includes narration from your captain and crew, as you learn more about these majestic creatures. Enjoy stunning views and photo opportunities while traveling along Maui’s exquisite coastline. Your family-friendly cruise comes with a guarantee that you spot a whale during your adventure.

If you like sea creatures, but have no desire to scuba dive, this tour offers an alternative. Relax on board a glass bottom boat where every seat is a window seat, and prepare for an underwater show. Divers bring animals such as octopus, urchins, crabs, and starfish up to the windows for viewing, making every trip a unique experience. This is a family-friendly experience that is fun for all ages.

Our 50-foot Santa Cruz sailing yacht carries up to 22 passengers for intimate sailing excursions. Scotch Mist is built for the Maui winds, and she was “first in class” in the prestigious Victoria-to-Maui Yacht Race besting her competitors by over 24 hours. The mast on this sailing yacht is over 65 feet tall and carries the main sail and billowing jib that moves us over the ocean waves at an exciting speed! As visitors return to Maui, we are following state and federal social distancing guidelines. We are using high-tech atomizing disinfectants at all check-in booths, seating areas, and vessel surfaces before and after each trip, and we have hand sanitizing stations set up on board. Crew and passengers will wear a mask except while swimming and snorkeling and enjoying on-board food and beverages. Set sail with us!

This tour departs from the historic Lahaina Harbor to find the majestic humpback whales that frequent the waters surrounding Maui in the winter months. Traveling in a small raft creates an intimate whale watching experience not found on the larger vessels commonly used on whale watching tours. Plus, the raft travels quickly, letting you spend more time whale watching and less time in transit.

Get a front-row spot on a whale watching tour by booking this small-group excursion off the coast of Lahaina. While larger whale watching boats are crowded and can make it difficult to get photos of whales, this inflatable raft-style boat gets all passengers close to the water’s surface for a prime vantage point. This makes the trip ideal for photographers and families with kids.

Snorkeling in Molokini Crater is undeniably one of the best parts about visiting Maui. Here in this crescent, submerged volcano off Maui’s southern coastline, over 250 species of fish inhabit a world-class reef. Experience water so exceptionally clear you can see down 75 feet, and swim with schools of tropical fish while cruising the vibrant reef. You can also just sit and suntan on the deck, with sweeping views of Haleakala set just off the back of the boat.

A trip to Molokini Crater grants visitors the chance to take in scenic ocean views from a catamaran and discover the world below the surface while snorkeling at the underwater lava formations of Turtle Town. The calm water and bountiful marine life make this an ideal snorkeling spot for everyone from first-timers to long-time snorkeling enthusiasts. Plus, a guide provides security and instruction for beginners.

The Scotch Mist is a fun and fast sailing yacht, built in 1982 for racing by famed builder Bill Lee in Santa Cruz, California. In fact, she is the fastest production line sailboat of her size in the world, having won “first in class” in the prestigious Victoria-to-Maui Yacht race, besting her competition by over 24 hours. The speed of this awesome sailing vessel is truly exhilarating! The serenity of your surroundings will leave you feeling completely relaxed and at ease. Enjoy one of our complimentary beverages local beer, white wine, sodas, juices & water, with champagne being added on the Sunset Sail, and let us do all the work!

Skip the overcrowded boat tours and enjoy a more intimate experience of Hawaii. Travel to the island of Lanai in the company of no more than 22 passengers. Make snorkeling stops off the island to see tropical fish, turtles, octopus, manta rays, and dolphins. This tour includes breakfast and snacks and your ticket supports active marine research and the work of Maui’s whale entanglement response team.

Sail to one of Hawaii's less-frequented islands on this snorkeling tour form Lahaina to Lanai, or the Pineapple Island. Snorkel beneath 300-foot tall cliffs near Shark Fin and Manele Bay, and look out for sightings of Lanai's resident pod of Spinner dolphins. This tour also includes breakfast and lunch to fuel a full day of fun.

Our Maui whale watching tour is truly an exceptional vacation value. You’ll enjoy a full two hour whale watch combined with snorkeling a beautiful coral reef.

Go snorkeling off the coast of Maui on this boat tour on board 'the Malolo,' a 55-foot (17-meter) power catamaran. Cruise to one of two snorkeling sites—either Molokini Crater or Coral Gardens—where you can swim along the reef system to watch for colorful fish and other marine life. The location is selected by the captain depending on the daily conditions. If you're lucky, you may spot turtles or whales, too. Equipment and instructions are provided by the crew. Lunch (hot dog and soda) by selecting the upgrade option when booking.

Discover the amazing array of marine life that populates Maui’s Molokini Crater during this small-group snorkeling trip. Head by boat to this long-extinct volcanic crater just off Maui, a top-notch snorkeling site where visibility often surpasses 180 feet (55m). Among the many creatures you may spot during your adventure are rays, tropical fish and variety of other wildlife. Finish your trip at ‘Turtle Town,’ another well-known snorkel site where you can glide through the water with Hawaiian Green Sea Turtles. Your snorkel trip also includes, breakfast, lunch, local guide and snorkel equipment.

Get a different perspective on Maui's whales on this kayak and snorkel adventure tour. Aboard a kayak, paddle through the calm Pacific waters, following your guide to the spots you're most likely to find humpback whales. Afterward jump into the ocean and snorkel the clear water amongst variety of colorful tropical fish, green sea turtles, and more. Throughout the day, get insights into the flora and fauna of West Maui from your guide.

Skip the crowded boat tours and embark on a more personalized snorkeling adventure in the waters around Lahaina. Make multiple snorkel stops and explore the underwater world with your guide, as well as sea cliffs, blow holes, and offshore pinnacles. You may also encounter the resident pod of dolphins. Use of all snorkeling gear is included, as well as lunch onboard.

Spot humpbacks as they travel through Maui’s warm waters on this 1.5-hour whale-watching excursion. Hop aboard a sturdy raft in Kihei with an expert naturalist as your guide, and jet to the southern coastline, which hosts one of the highest whale populations in Hawaii. Your guide will provide commentary about these fascinating creatures as you see them spout and slap the water. To keep this whale-watching tour intimate, your group is limited to 24 people.

Hawaii is home to an underwater wonderland of diverse marine life including whales, green sea turtles, and tropical fish. Make sure you see the best of Maui’s nature on this 3-hour whale watching and snorkel tour from Makena. Paddle through the calm, clear water in a kayak and keep your eyes peeled for sightings of humpback whales. Then, don snorkeling equipment to plunge into the water and discover tropical fish that inhabit a protected reef. This small-group tour is limited to 10 to maintain an intimate atmosphere.

VIP Whale Tour - limited to 12 passengers max. The Whales Love Us! Maybe it’s our Aloha? One thing is for sure, you will love getting up close and personal with the magical giants! You're experience will not just viewing whales, but listening live to the majestic whale songs through the use of our high performance Hydrophone Audio System which mixes the whale songs over gentle island tunes. Ali'i VIP Whale Tour Get the Royal treatment on our Ali'i VIP Whale Tour! We limit this tour to a maximum of 11 guests, so you have more opportunities to view the Humpback whales, and other sea life, in the most comfort possible. Our vessels are USCG rated to carry 26 guests, but this tour is all about you and your experience and is limited to 11 guests. The Ali'i VIP Whale Tour is only offered on Mondays, Wednesdays and Fridays.