Top Maui Cruises & Sailing

Leave the crowds of Ka’anapali Beach behind and step onto a premium sunset dinner cruise, where Maui’s coastline sets the stage for an unforgettable evening. Perfect for capturing stunning views, snapping share-worthy photos, or even spotting whales (if you’re visiting between December and April), this experience adds just the right amount of romance to your getaway.

Sail along the coast of Maui and enjoy a stunning Hawaiian sunset during this evening cruise from Lahaina Harbor. Get comfortable on a spacious catamaran and enjoy the views while you enjoy complimentary hors d’oeuvres and non-alcoholic drinks. If you’re traveling between December and May, you may even spot humpback whales while you sail.

Sailing off the coast of Maui is fun, but sailing off the coast of Maui at sunset, while enjoying dinner and drinks, is even better. This evening experience gets you out to sea just as the sun is setting, offering epic views paired with delicious food and cocktails, wine, and beer.

Cruise Maui's scenic coastline on a sunset outing aboard a catamaran whose two hulls offer increased stability, more deck space, and a sheltered cabin equipped with restrooms—all designed for a comfortable ride. An evening departure time makes the most of sweeping views along the shore, as the sun sinks over nearby Lanai. Stay refreshed with included soda, juice, and water, or visit the galley to purchase alcohol and snacks.

This Maalaea Harbor Sunset Dinner Cruise from Wailuku is perfect for couples or anyone looking to add a beautiful, sunset experience to their trip while in Maui. When booking, choose from multiple dinner options such as prime rib, baby back ribs, and a vegetarian penne pasta. During your cruise, sit back with tableside service and drinks included as your captain and crew take care of the rest and you take in the sunset with island-style music playing in the background.

Enjoy the ultimate Ma‘alaea premium dinner cruise with a 4-course meal served as the sun dips below the horizon. Sip on included Mai Tais or other beverages while soaking in incredible views of the Pacific, Lana‘i, and Moloka‘i. With only a select number of guests aboard, this cruise delivers an intimate, unforgettable evening.

Board the beautiful and spacious "Pride of Maui" catamaran for a relaxing sunset dinner cruise. Enjoy an open bar featuring craft beer and blended drinks, plus a generous buffet complete with barbecued ribs, chicken, roasted 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.

Embark an unforgettable sunset sail in Maui, leaving from Ka’anapali Beach. As the sun sinks into the gentle waves, leave the details to someone else while you enjoy mai tais, wine, and beer at the open bar, as well as a selection of appetizers. Experience a romantic happy hour at sea with drinks to get your Maui night started in style.

Observe humpback whales in their natural habitat during their return migration to Maui’s waters December–April. This whale watching adventure by high-speed catamaran provides a front row seat to fin slaps, flukes, and breaches. Underwater hydrophones help you hear whale songs, while the captain and crew provide the commentary. Juices and sodas are available on board to keep passengers hydrated.

Experience two of Maui’s premier snorkeling destinations without the need to arrange separate boat trips, meals, or equipment. This luxury yacht excursion combines snorkeling at Molokini and Turtle Town with onboard dining and comfortable amenities, creating a more relaxing day on the water. Included meals, equipment, and spacious surroundings allow you to focus on the marine life and scenery.

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the glassy, miraculous ‘au’au Channel is like floating inside an infinite sphere of color, surrounded by the islands of Maui, Lāna‘i, and Moloka‘i. Enjoy the best of performance sailing in Maui on our Conser 47' performance sailing catamaran. With spacious trampolines, shaded cabin seating, and a professional crew, this is the ultimate Maui sunset cruise. We invite you to relax, sip a cocktail, and watch the sky transform over the Pacific. Your sunset sail includes local appetizers and a full open bar with sparkling wine, white wine, and local beer. Experience the magic of Maui. This tour is perfect for all ages, with a limited capacity of 25 passengers ensuring a cozy atmosphere.

Rather than spending the most magical time of day inside a restaurant or hotel, treat yourself to this sunset dinner cruise aboard a catamaran. Enjoy included drinks and watch the sun go down behind the island of Lanai as you cruise along the Lahaina coastline. Then, indulge in a delicious 3-course dinner accompanied by the sounds of a local musician. Depending on the time of year, you might even spot humpback whales.

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.

Maui has some fantastic marine life, but large boats can scare creatures off. This small-group tour gets you closer to wildlife such as turtles and dolphins, without the crowds of traditional boat tours, but still has the benefit of an onboard marine naturalist guide to provide commentary and answer questions.

Explore Molokini’s best snorkeling sites on this small-boat excursion from Maui. Take a small boat to Molokini Crater for snorkeling at an uncrowded part of the Molokini shoreline to see colorful coral, fish, and sea turtles. You’ll also stop at Le Perouse Bay’s Turtle Town for swimming with turtles, and if it’s whale season, whale spotting is likely. Go places the larger boats can’t get to with local guides.

Soar above Maui on an unforgettable small-group parasailing experience off Kaanapali Beach, with all safety gear, guidance, and hotel pick-up included. You’ll get to soar above the sparkling water for a bird’s eye view as you cruise in a boat along the coastline. Enjoy incredible vistas of the gorgeous coastal scenery on this bucket list, fly-high adventure.

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that made Teralani famous.

Join us for an unforgettable West Maui Snorkel & Sail adventure! Departing from Maalaea Harbor, we’ll explore the coastline, stopping at the day’s best snorkeling spots to discover vibrant coral reefs, sea turtles, and diverse marine life. After a thrilling underwater experience, enjoy a delicious deli-style lunch and drinks. With stunning views and a relaxing sail, this excursion offers the perfect mix of adventure, nature, and relaxation.

This experience stands out by cruising out of Wailuku in a Kai II, a 53-foot boat (16 meters) with a 25-foot waterslide (7.6 meters) for an afternoon of snorkeling and fun in the water. Snorkel at Coral Gardens, Turtle Town, and, on rare occasions, at Molokini Crater. Get the chance to see whales from November through April.

Spend the morning on the water off the Maui coast aboard a 64-foot catamaran sailing to Lanai’i. The expert crew will find the best reefs to snorkel so you can see incredible underwater sea life. After your snorkel, return to the boat for lunch and stunning sea views in the golden afternoon light. Look out for playful spinner dolphins on the sail back to Maui.

Prebook this Molokini Crater or Coral Gardens snorkeling tour from Ma'alaea Harbor and have all the details of the afternoon taken care of for you, so you can enjoy your time in the water without the stress of planning the logistics. Your guide takes you on a 55-foot (16.7-meter) catamaran and picks the best snorkeling site based on the ocean’s conditions at that time. Plus, a hot-dog lunch and all snorkeling equipment are provided for you.

Dive in to explore West Maui's underwater world during this half-day snorkeling cruise from Ka'anapali Beach. Travel to some of the island's best snorkel locations to see green sea turtles (honu), schools of colorful tropical fish, and maybe dolphins, or even humpback whales (seasonal). Dive in with the included gear, then enjoy lunch onboard afterwards, with drinks included.

Live drumming, traditional dances, and fire-knife performances create a thrilling luau dinner show centered on traditional Hawaiian culture. A beachfront sunset and dinner buffet (with special kids' options available) makes for an unforgettable evening. Book a general admission ticket for dinner and a show, or opt for the VIP choice to guarantee priority buffet access and front section seating.