Top Hawaii Sailing Tours

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.

Swap the crowds of Waikiki Beach for a relaxed Hawaiian sunset cruise experience. Relax with included snacks, soft drinks, and coolers with ice for any additional beverages you bring 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.

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.

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.

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 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.

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.

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.

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.

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.

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.

Escape the crowds of Waikiki Beach and enjoy the magic of a Hawaiian sunset on board a spacious double-decker catamaran. Roomy decks provide panoramic views of the Oahu coastline and a submerged glass-bottom viewing room offers the chance to observe marine life such as dolphins, whales, sea turtles, and native fish.

Sail along the Maui coast on a 47-foot catamaran at sunset for an unforgettable evening adventure—and leave the logistics to someone else. Set off from Lahaina and enjoy the majestic Maui ocean scenery during the colorful sunset hours. A selection of hors d'oeuvres, wine, beer, and non-alcoholic drinks are available on board so you can relax and have fun.

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.

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.

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 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.

Embark on a sunset sail aboard a luxury 55-foot catamaran in Maui as the sun sinks into the gentle waves—and leave the details to someone else. Sip unlimited cocktails, wine, and beer at the open bar and enjoy a selection of locally inspired hors d’oeuvres. See stunning views of Maui, Lana‘i, and Kaho‘olawe in the golden light as you relax on the boat.

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.

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.

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.

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.

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.