Top Hawaii Sailing Tours - page 3

Embark on an evening adventure and swim near Hawaii’s manta rays. Start the tour with a sunset sail on a comfortable catamaran 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.

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.

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.

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.

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.

Embark on 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. Experience a golden happy hour at sea with music and drinks to get your Maui night started in style.

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.

See the Waikiki coastline like never before on a sunset dinner cruise on board a 65-foot (20-meter) catamaran. Set sail from Waikiki and enjoy unobstructed views of the beach with a backdrop of the Ko`olau mountains. As the sun sets and the Honolulu skyline lights up, toast your day in paradise with two included drinks and a delicious dinner.

Save time and money when you 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.

Hop aboard The Universe, or your sailboat, to watch the sunset in Waikiki on this small-group tour. Your captain navigates, so you just need to relax. Sip on provided soda and water and snack on chips and crackers as you cruise along the water. Check out Diamond Head as the sun goes down and get some awesome photos.

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide along the iconic Gold Coast as the sun sets, painting the sky with vibrant colors that illuminate Waikīkī’s skyline. This tranquil evening experience is perfect for capturing stunning photos and enjoying the serene atmosphere of paradise. Whether you're a couple, family, or sunset enthusiast, this cruise offers a unique way to unwind and appreciate the beauty of Hawaii. Enjoy a refreshing swim in the crystal-clear waters off Waikīkī Beach. Sail along the iconic Gold Coast during the magical golden hour. Capture stunning photos of the sunset and Waikīkī skyline. Ideal for couples, families, and sunset enthusiasts alike.

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.

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.

Perfect for jetlagged early birds, this intimate morning yacht tour from Honolulu takes you to Turtle Canyon in a small group. 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.

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.

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.

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.

Sail along the Maui coast on a humpback whale-watching excursion in the ʻAuʻau Channel—and leave the logistics to someone else. See these gentle giants spouting, tail-slapping, and maybe even breaching in their natural habitat from a comfortable boat, crewed by local experts. Enjoy the comfortable boat, ocean scenery and wildlife spotting, and look out for mother and whales and their calves because this is their winter breeding ground.

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.

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.

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, unlimited non-alcoholic beverages, and 2 complimentary adult beverages as you cruise around. From December to March, the tour includes a whale watch to see humpback whales and extends by 30 minutes.

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.

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.

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.