Top Hawaii Sailing Tours - page 2

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.

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.

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.

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.

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.

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.

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while searching for dolphins and sea turtles in their natural habitat. Families and nature enthusiasts will appreciate this relaxing cruise, which offers a chance to spot marine life up close. With an open bar option available, enjoy refreshments as you soak up the sun. If you don't see any whales on your first sail, you can return for a complimentary second sail within the season. - Complimentary second sail if no whales are spotted on the first trip - 1.5-hour sail from the beach with stunning views - Family-friendly experience suitable for all ages - Open bar included!

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.

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)!

Take a break from the crowded beaches and head out on the water for a half-day sail along the Kona Coast aboard a spacious catamaran. Take advantage of multiple onboard amenities such as the shaded cabin and sunny splash nets as you sail to Kealakekua Bay. See the Captain Cook Monument and don your snorkel gear for the chance to observe vibrant coral and tropical fish.

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.

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.

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.

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.

Experience the ultimate Friday night in Waikiki aboard a fireworks cruise! After sunset, get ready for a spectacular show as fireworks light up the city skyline. Sip on premium drinks from the onboard bar and enjoy the illuminated night sky. This party promises unforgettable views and a vibrant atmosphere that will make your evening truly special. Book now and experience an amazing night on the water, surrounded by the magic of fireworks and the beauty of Waikiki.

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.

This afternoon sail in Maui offers a chance to see humpback whales in the ‘Au ‘au channel. Enjoy snacks, water, sodas, and alcoholic beverages aboard a small boat for an intimate experience focused on whale watching. Chat with your crew along the way and learn all about whale behavior as you keep an eye out for the majestic marine mammals.

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.

Experience the picturesque beauty of an Oahu sunset the way it was meant to be seen—from the water while sailing on a catamaran. On this 2-hour cruise, watch for dolphins and whales, and enjoy a delicious charcuterie box with complimentary cocktails. This sailing experience is ideal for couples looking for a romantic evening on the water or families wanting to create lasting vacation memories.

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.

Discover a side of the Big Island of Hawaii that very few other travelers get to see on this one-of-a-kind submarine tour. Choose from multiple start times, head to the Kona coastline, and board the submarine. As you descend towards the colorful reef, peer through the portholes and spot fish and other marine life. Along the way, your on-board naturalist guide provides in-depth commentary about the aquatic sights.

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.

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.