Top Hawaii Sailing Tours - page 2

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.

Discover the clear blue waters of Molokini Crater with a guide to make sure everyone is having fun and staying safe on this group snorkeling experience. Begin with breakfast on board, and end with lunch before you head back to the harbor. In between, go snorkeling and look for sea turtles in the summer and whales in the winter.

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.

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.

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.

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.

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 aboard a 54 foot catamaran for a dolphin and turtle cruise from A-Bay that includes snorkeling gear and assistance from on board snorkel guides. Since the catamaran has ample deck space and shaded areas to relax, it’s a comfortable, uncrowded way to cruise the coast, and you’ll have the chance to spot humpback whales during the whale watching months of December through April.

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.

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.

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.

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.

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.

Cruise Maui's scenic coastline on a sunset outing aboard a catamaran whose two hulls offer increased stability, more deck space, and a sheltered cabin equipped with restrooms—all designed for a comfortable ride. An evening departure time makes the most of sweeping views along the shore, as the sun sinks over nearby Lanai. Stay refreshed with included soda, juice, and water, or visit the galley to purchase alcohol and snacks.

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).

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that made Teralani famous.

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). Our snorkel, swim and sail is the perfect combination of warm sun, refreshing salty water, and breezy adventure sailing. Snorkel equipment and drinks are all included.

Embarking on a sunset sail is the perfect way to end a day in Waikiki. With so many options, you'll want to be sure to make the best choice. This cruise promises comfort and relaxation by taking you out onto the ocean aboard a spacious twin-hulled catamaran. As the crews do the hard work, you can simply relax on board and feel the warmth of the setting sun.

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.

Dive beneath the waves to explore Maui’s colorful fish, vibrant coral, and graceful sea turtles on this 6-hour snorkel excursion to Honolua Bay. Experience one of the island’s most popular snorkel spots with the help of a certified marine naturalist before heading to a second site for more underwater adventure. An included breakfast, barbecue lunch, and periodic sightings of wild dolphins help add to the experience.

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.

Escape the hustle and bustle of land and soak up the sun and ocean breeze while taking in the sights of the Kona coastline on this sailing trip aboard a comfortable 53-foot catamaran. As you glide across the blue water, keep an eye out for marine wildlife such as dolphins and humpback whales during migratory season. Enjoy a full premium bar with tropical cocktails, beer, wine, soda, and juice on board.

Cap off a day in paradise with a sunset cruise from Waikiki. Unwind as you glide across the ocean and soak in views of Waikiki and Diamond Head (Lē‘ahi) crater at golden hour, while looking out for turtles, dolphins, and (during migration season) whales Bring your own drinks (no glass) to enjoy your favorite beverage while cruising.

Perfect for jetlagged early birds, this intimate morning yacht tour from Honolulu takes you to Turtle Canyon in a small group of no more than six. Watch the sun rise over Diamond Head as you sail towards Turtle Canyon's reef, then jump into the water to snorkel in the company of sea turtles and colorful fish.