Top Hawaii Sailing Tours

This half-day boat cruise takes you to the two best snorkeling sites in Kealakekua Bay: The reef beneath Captain Cook's monument and the underwater lava formations of Red Hill. In addition to breakfast and lunch, your guides provide all necessary equipment, basic snorkeling tips, and identification charts to help you spot fish and dolphins in their natural habitat. Don’t forget your camera—the route showcases sweeping views of the Kona coastline.

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.

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.

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.

The white-sand beaches and volcanic landscapes of the Kohala Coast are even more atmospheric at sunset. With this tour, set sail at dusk and admire the views onboard a comfortable catamaran. As you cruise along the coast, sip a selection of wines, beers, and soft drinks, and enjoy a variety of snacks.

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.

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.

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.

Set sail from Waikiki on board a beautiful catamaran. Enjoy stunning views of Waikiki Beach and Diamond Head as you glide over the water while enjoying soda and optional upgraded Hāwea premium all-inclusive beverages. As the sun goes down, you can hang out on the deck or have a fun ride on the net.

Sail aboard a catamaran to Molokini crater, one of Maui’s best snorkel sites. The volcanic atoll off the south coast is a natural marine preserve, home to 250 species of tropical fish. Join the crew at the helm of “Paragon II” as Maui’s afternoon trade winds get the boat to this top destination.

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.

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.

Relax in the Maui sunset, taking in orange and pink evening skies as you glide over the waves on this catamaran trip including dinner. Take in seascape views from the boat’s spacious deck which features unobstructed views of the ocean, or sip a tropical drink at the fully licensed onboard bar before tucking into a dinner crafted from fresh local ingredients. A professional photographer onboard captures magical memories available for purchase.

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. Note: We are a beach loading catamaran and you might get wet up to your knees boarding.

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.

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.

Sail up the scenic Kona coastline, getting views of ancient lava flows and verdant cliffs, and stopping at the Captain Cook Monument, on this afternoon sail in Kealakekua Bay. Slip into the water using the provided snorkeling gear to see vibrant schools of fish, living coral, and even pods of spinner dolphins. Learn about the area's underwater flora, fauna, and ecosystem through guided commentary.

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.

Step on board one of Honolulu's most-recognizable catamarans and set sail along the south shore of Oahu. Enjoy free-flowing drinks as you soak up the sun and stunning views of the Waikiki coastline and Diamond Head. As you cruise, look out for marine life such as dolphins and whales splashing through the waves.

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 available within Waikiki included.

Our sunset turtle snorkeling tour delivers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and unforgettable views in one trip. We reach Turtle Canyon quickly, giving you more time in the water to swim with Hawaiian green sea turtles in clear, warm conditions. Beyond snorkeling, enjoy kayaking, stand-up paddleboarding, sea scooters, and swimming—all included at no extra cost. The highlight is the timing. After your activities, relax on board as the Waikiki sky fills with vibrant sunset colors, with Diamond Head as your backdrop. The experience ends with a peaceful sunset sail, complemented by charcuterie and cocktails. With a friendly, attentive crew and beginner-friendly guidance, this tour is perfect for everyone—from first-time snorkelers to experienced ocean lovers. More than just a tour, it’s a memorable Waikiki experience you won’t forget.

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.

Enjoy a unique perspective on Oahu, and catch one of Hawaii’s famous sunsets from the water, on this sunset catamaran cruise from Honolulu Enjoy a barefoot boarding from Waikiki Beach, then sip on a beer, wine, or cocktail from the onboard open bar as you admire the unobstructed views of the coastline and the sun setting into the ocean.