Top Hawaii Sailing Tours

Waikiki's best coastline views are only fully accessible from the water—and this cruise is timed specifically to coincide with sunset, putting passengers on the ocean at the right moment without the cost of arranging a private vessel. The option to swim directly from the boat is available during the sailing, with the Waikiki shoreline as the backdrop throughout.

With 17 miles of pure shoreline splendor—4,000-foot cliffs, emerald valleys, cathedral spires—Kauai’s Na Pali coast claims some of the country’s best sailing and snorkeling. On this tour, you’ll cross both off your list, hopping aboard a sailing catamaran for an unforgettable adventure. Between sitting down to breakfast and lunch, you’ll spot whales, snorkel amongst turtles and rays, and see one of the most spectacular coastlines on the planet.

Experience the beauty of Oahu’s wildlife on a two-hour cruise that’s sure to leave you in awe. Step aboard a roomy catamaran and set sail, admiring Hawaii’s lush coastline. Take a dip in the water and keep your eyes peeled for green sea turtles, dolphins, whales, and monk seals. Premium snorkel equipment and onboard refreshments are provided for a seamless sailing experience.

Sail Waikiki’s coast on a spacious custom-built trimaran boat that is made for smooth and stable rides. Enjoy panoramic open-air views and ample seating options, including netted areas, benches, and a shaded lounge. Bring your own beverages and relax in your chosen spot, taking in the unrivaled beauty of the Hawaiian sunset and Diamond Head crater.

Experience one of Hawaii’s famous sunsets on a cruise along Waikiki’s coast. Board your vessel and watch the sky change colors as the sun starts to dip below the horizon. While you sail, keep your eyes peeled for dolphins and, from November to May, even humpback whales. You can also enjoy views of Waikiki landmarks including Diamond Head.

Experience an unforgettable catamaran cruise in Maui. Sail on a 65-foot boat along the Pacific Ocean where the professional crew takes care of everything—including photos (fee to purchase). Snorkel at a reef with guaranteed sea turtles, and after enjoy a taco lunch on the boat with margaritas and beer. Relax on the cruise back to Maui—look out for whales in season and beautiful views all year long.

Escape the crowds of Waikiki Beach with this swim-and-sail catamaran tour. Head out onto crystal-clear water and look out for fish, turtles and dolphins on your way to a top swimming spot. Jump into the water or hang out in the onboard lounge areas then continue your journey to Diamond Head Crater.

Snorkeling in Molokini Crater is a frequent bucket-list experience for Hawaii visitors. Here in this submerged volcano off Maui’s southern coastline, more than 250 species of fish inhabit a world-class reef. Experience water so exceptionally clear you can see down 75 feet (23 meters), and swim with schools of tropical fish. This half-day tour from Maalaea Harbor takes care of all the logistics for you.

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque inter-island channel, showcasing the beauty of Maui, Lāna‘i, and Kaho‘olawe. Guests can relax on trampolines or in shaded seating while enjoying locally-inspired appetizers and a selection of beverages, including cocktails, beer, and wine. From December to March, keep an eye out for majestic humpback whales as they migrate, often providing unforgettable sightings during the sail. - Enjoy a scenic 2-hour sunset sail aboard the 55-foot Akialoa catamaran. - Indulge in a selection of local appetizers and an open bar of drinks. - Limited to 48 passengers, ensuring a cozy and intimate experience. - Spot migrating humpback whales from December to March for a unique wildlife encounter.

This lively sunset cruise is great for groups as well as solo travelers. In fact, you’re likely to make fast friends with other passengers over conversation and cocktails including wine, champagne, and a variety of domestic and premium local beers from Maui Brewing. Have a signature cocktail, the “Holokai Hooch,” as you savor the sunset over Oahu.

The Na Pali Coast is one of the world's most spectacular coastlines, and one of the best ways to see it is by cruising along the coastline as the sun goes down. This sunset cruise takes you out onto the ocean in a comfortable catamaran. As you glide past Na Pali's jagged peaks and emerald valleys, enjoy a complimentary Hawaiian-style dinner and toast the sunset with a Mai Tai.

Embark on an adventure to Turtle Canyon on this catamaran excursion from Waikiki. Board your vessel and spend your time snorkeling in the pristine waters off the coast of Oahu. See green sea turtles being cleaned by fish and finger reefs as well as octopuses and starfish. The reef is quite shallow so snorkelers of all levels are encouraged to join.

Experience the magical Hawaiian sunset from the water on this evening catamaran cruise from Anaehoomalu Bay. Set sail along the scenic Waikoloa and Kohala-Kona coastline, sip a glass of wine as you gaze out across the Pacific, then relax on deck as you watch the sunset over the Big Island.

Enjoy unparalleled views of Diamond Head that are difficult to get on land when you join this lively sunset cruise from Kaka'ako Waterfront to Waikiki. Enjoy complimentary alcoholic and non-alcoholic drinks, good music, and a playful crew aboard a catamaran while you watch the sun dip below the horizon. Please note that all guests, including infants, need tickets, and the atmosphere can be party-like, so parents should consider this when bringing children.

Embark an unforgettable sunset sail in Maui where everything is taken care of to ensure a fun and relaxing time. As the sun sinks into the gentle waves, enjoy craft cocktails, wine, and beer at the open bar, as well as a selection of snacks. Experience a golden happy hour at sea with music and drinks to get your Maui night started in style.

Swap the crowds of Waikiki Beach for a relaxed Hawaiian sunset experience on this small-group cruise. Relax with a cold beverage and included snacks as you cruise along the Waikiki coastline toward Diamond Head while the sun dips into the ocean. Look out for pods of dolphins and large Hawaiian green sea turtles that frequent the surface.

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.

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.

Take the chance to dive into the crystal-clear waters of Oahu and experience snorkeling alongside wildlife during this luxurious catamaran tour. Keep an eye out for turtles as you explore Waikiki's Turtle Canyon. Then, take a break to relax before going paddleboarding, kayaking, and sea scooter riding. Guided by a passionate and knowledgeable team, embark on a fun adventure in nature with convenient hotel pickup included.

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buffet lunch is served and our complimentary bar is open after you are done snorkeling. We hoist the sails and return to Ka'anapali Beach while viewing the amazing coastline of Maui.

Escape the hustle and bustle of Kona and round-out your day on the Big Island of Hawaii in style with a relaxing sunset cruise. Aboard a comfortable and spacious catamaran, take in the views as you sail along the Kona coastline and toast the sunset with an included beverage or two.

Combine two must-do experiences to enhance your vacation in Hawaii. First, board a spacious catamaran for a sunset cruise along the Kona coast. Then slip into the ocean for a snorkel adventure with manta rays. Guides provide instruction and ensure your comfort—you're also guaranteed a manta ray sighting, or your next booking is free.

Turtle Canyon sits just off the Waikiki coastline and is one of the most reliable spots on Oahu to snorkel alongside Hawaiian green sea turtles—but reaching it requires a boat. This catamaran tour departs from Waikiki, with a guide leading the snorkeling session and a light snack included on board.