Top Hawaii Sailing Tours

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.

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.

There is no better way to soak up the beauty of Waikiki than by watching the sunset from the water. This evening cruise is timed to coincide with the sun slipping below the horizon and painting the sky in unforgettable colors. You can spend your time relaxing on the deck or take the opportunity to jump off board and swim in the ocean.

The Na Pali Coast is one of the world's most spectacular coastlines. And one of the best ways to see it is with this sunset cruise. As the sun sets, glide past the jagged peaks and emerald valleys from aboard a luxury catamaran,

Discover all the vibrant marine life that calls Turtle Canyon’s reefs home—and enjoy an accessible way to snorkel and explore—on this family-friendly catamaran trip. Make your own way to the Kewalo Harbor, and hop aboard your well-appointed catamaran: snorkels, fins, masks, and more are all provided on board. Once you make it to the reefs, dive in, spot sea turtles and other marine life, and admire the underwater scenery.

Explore Oahu's waters on this submarine-style glass-bottom boat ride aboard the Atlantis Submarine. During this family-friendly adventure, learn about the local fish, coral and other animals in this marine habitat through your guide's informative commentary. Please be aware all passengers must be 36" or taller to ride. Descend 100 feet (30 meters) under the surface of the water without getting wet. 

Set sail into the sunset aboard a sailing yacht with this cruise. You'll hop aboard the Scotch Mist in Lahaina and sail out into the Pacific, where you'll have your choice of champagne, local beers, white wine, soda, juices, and bottled water. Best of all, group sizes are capped at 22 people so you won't have to worry about crowds.

The Big Island of Hawaii has a diverse ecosystem unlike anywhere else on the planet, and on this day-long nature tour, experience the beauty of its black-sand beaches, thundering waterfalls, and Hawaii Volcanoes National Park. If you’re lucky, find Hawaiian green sea turtles basking on the coast. Since the tour only requires a moderate amount of walking, it's an educational adventure for travelers of all ages, with snacks and refreshments included.

On this exciting Kona submarine tour, dive deep below the cobalt waters just off the Kona coast, where an entire world of fish and marine creatures is waiting just below the surface. As the submarine descends towards the colorful reef, peer through the portholes at fish that swim to within inches of the submarine windows, and experience the sense of peace and calm in this world beneath the waves. This is a great way to explore underwater without even getting your hair wet, and, if you’re very lucky, there’s even the chance you could see a passing shark.

The Kaneohe Sandbar is one of the best places around Oahu for swimming and snorkeling. But, without your own boat, it's tricky to get there. This boat trip does all the hard work for you so that you can relax on board as you cruise to the sandbar then spend your time as you please, whether by jumping into the water, spotting turtles or just soaking up the sun and scenery.

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.

Eat, drink, and be merry on a sunset cruise aboard a luxury catamaran. Sail the waters off Maui as you experience the ho’okipa (hospitality) of the crew and panoramic views. Enjoy an array of premium appetizers and a full bar—three alcoholic drinks are included in the price. There’s also a marine biologist on board to comment on any wildlife you may encounter or answer questions about the local flora and fauna.

Go whale-watching off the coast of Oahu on this excursion from Waikiki or Ko Olina. During the months from December to May, pods of humpback whales migrate through Hawaii's warm waters, and this tour guarantees whale sightings. With a small group of people, watch the gentle giants swim, feed, breach and play around your boat. In the rare event that you don't see any whales, you will be allowed to do the tour again for free. Snacks are included.

This comprehensive tour of Oahu hits many of the island’s most iconic locations such as the Dole Plantation, Waimea Valley, Shark's Cove, Byodo-In Temple, Halona Blowhole, and more. You’ll also visit several beaches where you’ll have time to take photos. Along the way, sample tropical fruit, macadamia nuts, coconut water, and other island fare.

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 with included snorkel gear, swim noodle, and a wetsuit. Afterward, enjoy juice, soft drinks, or hot cocoa with cookies; beer, wine, and cocktails are available to purchase.

Ensure you find some of the best snorkeling sites in Hawaii on this sail and snorkel adventure leaving from Keauhou Bay Pier. Set sail along the Kona coastline toward the Captain Cook Monument, where your adventure begins. Jump into the clear water to explore the vibrant reef of the marine sanctuary of Kealakekua Bay, which is home to schools of colorful fish and pods of spinner dolphins. Your tour includes breakfast, lunch, and equipment such as snorkeling gear and boogie boards.

Enjoy stunning coastal views only available from the water during this sailing tour down Hawaii's Au'au Channel. Relax onboard a comfortable, well-equipped sailing yacht with a full captain and crew, enjoying complimentary beverages such as wine, local beer, or soft drinks.

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 a half-day 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.

Sail along the Kona coast aboard a spacious catamaran during this half-day tour to Kealakekua Bay, and take advantage of multiple amenities like the shaded cabin and sunny splash nets. Start with a continental breakfast, then build your own sandwich after a snorkeling session (equipment and instruction included). Beer, wine, and liquor are available to purchase.

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.

Embark on an evening adventure and swim near Hawaii’s manta rays. Start the tour with a sunset sail on a comfortable trimaran to ‘Manta Ray Village’. After a safety briefing, put on your snorkel gear and spend an hour in the water using a state-of-the-art, lit up flotation device to stay on the water’s surface and observe the manta rays bellow as they feed on plankton. Finally climb aboard the boat and warm up with hot chocolate and snacks as you return to shore.

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.

Enjoy the rare opportunity to see wild manta rays in their natural environment along Hawaii's Kona Coast. With this small-group cruise, set sail at night when the manta rays are most active and use a lighted floatation device to attract plankton—the rays' food of choice. With an experienced guide to ensure a safe experience for all parties, head into the water to float and snorkel as you admire the rays in action.

Discover the beauty of Oahu from the perspective of the water during an afternoon sail. Keep an eye out for a variety of marine life such as dolphins and whales. See local landmarks including the Diamond Head Lighthouse during the sail. Catch a glimpse of Koko Head and Koko Crater, and if the conditions are right, see all the way to Molokai, Maui, and Lanai.