Top Oahu Sailing Tours

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.

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.

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.

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.

Beat the crowds on land and soak up the beauty of Waikiki from the water on this sunset cruise that is timed to coincide with the sun slipping below the horizon and painting the sky in unforgettable colors. Choose to relax on deck or jump off to swim in the ocean.

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.

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.

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.

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.

You’re guaranteed to see an array of endemic reef fish, colorful corals, and other unique marine creatures that call the Hawaiian islands home.

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!

Epic 34' catamaran sailing and snorkeling in Waikiki Bay. With Diamond as the back drop you lay back and enjoy the amazing views.

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.

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a smaller guest capacity and open-deck layout, it offers an intimate, laid-back vibe perfect for couples, families, and small groups. Sail along the Waikiki coast beneath our iconic rainbow sail—bold, colorful, and instantly recognizable. It's the perfect backdrop for stunning photos and unforgettable memories. Choose General Boarding (includes one complimentary drink) or upgrade to Mana Premium for early boarding and all-inclusive island-style cocktails. With a closer-to-the-water design, friendly local crew, and relaxed pace, this isn’t just a sunset cruise—it’s an authentic aloha experience. Feel the ocean breeze, soak in golden skies, and sail into the magic of Waikiki like a true islander.

Swap the crowded boat tours for the chance to explore the ocean your way with this private catamaran charter from Honolulu. Glide across the ocean in comfort on board a sleek 48-foot (15-meter) catamaran and take your pick from three activity options: snorkeling, swimming near Diamond Head, or sailing down the coastline to take in the island views and look for marine life.

Swap the crowded catamarans for the chance to soak up Hawaii's natural beauty from a spacious yacht, in the company of just your partner. This private Waikiki sunset cruise is the perfect romantic experience for couples and takes you along the Waikiki coastline, all the way past Diamond Head, in time to see the sun setting over the ocean.

Perfect for families, couples, and ocean lovers seeking an unforgettable Hawaiian experience. Witness the majestic whales and stunning sunsets on the North Shore of Oahu. Explore the crystal-clear waters aboard your Summer snorkel charters. Swim along vibrant tropical fish, turtles and stunning coral reefs while enjoying personalized service and local expertise. The Ho’o Nanea catamaran offers a unique vantage point for observing marine life during the prime whale watching season from December-May or snorkel season May-October . Enjoy a relaxing cruise, where knowledgeable guides provide insights into the local wildlife and culture. Experience the vibrant colors of sunset from the water. This tour ensures personalized attention and an intimate experience with Hawaii's natural beauty. - 2 to 2.5-hour whale watching or sunset cruise - 3-4 hour snorkel charters - Knowledgeable guides sharing local insights and marine lore

Experience the joys of whale watching in Honolulu during this two-hour tour that guarantees sightings. Hop onto a modern trimaran boat with spacious seating, unobstructed views, and protective shade. Learn from onboard naturalists as you watch humpback whales breaching against the backdrop of Diamond Head. Conveniently located near most Waikiki hotels at 95 Holomoana St, you can bring your own drinks or snacks.

Watch the sun glow over the Pacific Ocean and spot wildlife from whales and turtles to dolphins (if you’re lucky) with this exclusive catamaran snorkeling adventure. Relax onboard a comfortable vessel with padded seats and ample space, or hop into the water with the provided snorkeling gear, finding out what's below the surface—and seeing Hawaii's colorful underwater world.

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.

Wake up in the morning and enjoy a sail around Oahu aboard a traditional, all-wood Polynesian canoe. This small-group tour has a strong focus on Hawaiian heritage and guests can learn about the stories and history of the tropical state. While onboard, guests also enjoy hands-on activities like making food, clothing, and tools with traditional items.

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.

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.