Top Hawaii Sailing Tours

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. You can go at the best time of day to snorkel (before 1pm) and see turtles, dolphins, eels, rays, octopus, big schools of tropical fish, and humpback whales (whale season is December - April). If you decide that you want to add to your trip, it’s no problem. It’s your boat and you decide the music, where you go, and rest assured you have the best crew to keep you safe at sea.

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.

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.

Swap the Waikiki crowds on land for a serene 2-hour sunset experience aboard a catamaran. Set sail along the Pacific waters off Oahu as the sun sinks into the ocean and enjoy complimentary pupus (appetizers) while taking in views of Diamond Head and Waikiki as it lights up in the evening.

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.

Humpback whales migrate to Hawaiian waters between December and April to give birth and breed, and seeing them from shore is hit-or-miss without knowing where the pods are concentrated each day. This whale-watching tour sails from Honolulu to the areas where the humpbacks are active, with sightings of dolphins and green sea turtles also possible across the route.

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.

Set sail down the Kona coastline aboard a catamaran, arriving in the Kealakekua Bay Marine Preserve for an afternoon of snorkeling. Splash into the turquoise waters near the Captain Cook Monument, and search for pods of spinner dolphins that frequent the bay. All equipment is provided along with light snacks and reef-safe sunscreen to make the trip convenient.

Oahu's Turtle Canyon is teeming with Hawaiian green sea turtles (known locally as *honu*), but it's difficult to access on your own. Skip the stress and board this catamaran cruise that departs from the only pier in Waikiki. Learn about the life, behavior, and cultural significance of the sea turtles, then jump into Turtle Canyon's protected tropical waters to swim among them.

Get a front-row seat for Waikiki's famed Friday night fireworks display. This evening cruise from Honolulu offers 360-degree, open-air views and a romantic experience to remember. Enjoy a complimentary alcoholic welcome beverage as you embark, then settle in and enjoy the scenery as the sun goes down and the fireworks light up the sky.

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.

The waters off the coast of Maui are often home to majestic humpback whales. Set sail from West Maui on this catamaran whale-watching tour as you attempt to catch a glimpse of the marine giants in their natural habitat. The onboard hydrophone will even let you listen to the whales’ song as you travel.

Experience the magic of Waikiki's Friday night fireworks aboard a cozy catamaran. Enjoy views of Diamond Head and the ocean as the crew share stories about local culture and marine life; you might spot turtles, dolphins, or whales. Bring your favorite beverages (BYOB, no glass), sip complimentary green tea or hot cocoa, and soak in authentic aloha vibes during this memorable evening.

Experience an unforgettable catamaran cruise in Maui with two snorkeling stops—and leave the logistics to someone else. Sail from Kaanapali Beach to snorkel at two reefs, with the chance to swim with sea turtles and other marine wildlife. While on board the boat, you’ll enjoy breakfast, a BBQ lunch, and an open bar. Don’t forget to look out for dolphins and whales (in season)!

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.

Kauai’s Na Pali Coast—17 miles of world-renowned landscapes—is certainly best appreciated from the water. Experience it in style aboard a sleek catamaran, crew greeting you with mai tais and a sense of aloha. You’ll catch moments with spinner dolphins and sea turtles, relax over dinner, and raise a glass of Champagne when sunset hits this magnificent slice of the Garden Isle.

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.

Every Friday night, the Hilton Hawaiian Village puts on a beautiful fireworks display. Rather than watching them from the beach, take to the water for a front-row view on this evening cruise off Waikiki Beach. Plus, enjoy an open bar, making this a fun and affordable way to kick off the weekend. This is a great option for families and group celebrations such as birthdays and bachelorette parties.

This combination snorkeling and sailing adventure is perfect for families and nature enthusiasts. Swim with green sea turtles, tropical fish, and other marine life in Turtle Bay near Honolulu. Next, enjoy a cruise around Diamond Head in search of spinner dolphins, and in the winter months, humpback whales. Have some complimentary drinks and snacks as you savor the natural beauty that surrounds you.

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.

Experience an important part of Hawaiian culture during your vacation and sail on a traditional Polynesian canoe. Join a small group and board the all-wood, double-hulled vessel for a sail along Waikiki's coastline at sunset. Hear myths, legends, and stories of native Hawaii and enjoy cultural activities like making food, clothes, and other traditional items.

Set sail and get up close with Waikiki’s majestic wildlife on this two-hour cruise. Board a spacious catamaran and glide across the water, admiring picturesque scenery of Oahu’s coast while searching for sea turtles, dolphins, coral, and vibrant fish. Stop to swim and snorkel in the turquoise water, or relax on the spacious deck.

Turtle Canyon lies just off Waikiki and is a top spot to snorkel with Hawaiian green sea turtles, but finding the best spots requires going with an in-the-know guide. This 2-hour catamaran tour includes snorkeling equipment and a professional guide to lead your adventure along the Waikiki coastline. Swim with turtles and tropical fish or relax on deck while enjoying ocean views.

Explore Oahu's waters on this submarine-style 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. Descend 100 feet (30 meters) under the surface of the water without getting wet in a vehicle that is quiet and pollution-free, so marine life is undisturbed.