Top Oahu Sailing Tours

Experience Waikīkī above and below the water with a snorkeling and parasailing combo. Cruise aboard a glass-bottom boat to a known Hawaiian green sea turtle—or honu—hangout. After a safety briefing and gear fitting, join an in-water guide to explore the reef and look for turtles and tropical fish. Guests who remain aboard can enjoy the glass-bottom viewing area. Wildlife sightings are not guaranteed. Then soar 1000 feet above Oʻahu’s south shore for sweeping views of Diamond Head, Waikīkī, and the Pacific. Flights are tandem or triple; single flights are not offered. The parasailing boat may carry up to 15 passengers. The activities may have separate check-in instructions and departure times. Review your confirmation for scheduling and arrival details.

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.

Swap the hustle and bustle of Honolulu for a day out on the ocean on this relaxing afternoon cruise. Soak up the sun and sea breeze as you sail along the coastline, past Diamond Head, aboard a spacious and comfortable catamaran. Relax on board while looking out for spinner dolphins, Hawaiian sea turtles and (in season) humpback whales.

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.

Enjoy a stunning sunset cruise along the Waikiki coastline, where the heat softens and Diamond Head transforms into a silhouette against the vibrant sky. Departing from Kewalo Basin, this 90-minute journey offers panoramic views of Honolulu as city lights flicker to life. Experience the unique glass-bottom viewing area to see the ocean beneath you while savoring light snacks and refreshments. Ideal for couples, families, and celebrations, this cruise is a perfect way to end your day in paradise. - Daily departures from Kewalo Basin Harbor, 5:30–7:00 PM - Includes light snacks, refreshments, and panoramic sunset views - Glass-bottom area for a unique viewing experience - Suitable for all ages; children must be accompanied by an adult

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.

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

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.

Friday Night Fireworks in Waikiki Beach is a major tourist draw each week. Avoid the crowds than congregate on the beach and surrounding streets by enjoying the spectacle from a boat as you cruise along the coast of Waikiki. You'll enjoy unobstructed views of the fireworks from the water and plenty of space to move around. The company provides light snacks and refreshments and you can bring your own beverages.

Wake up to the serene beauty of Waikiki on the Morning Coffee Cruise, where you can savor locally roasted Ali’i Coffee Co. and fresh pastries while gliding along the coastline. This 1.5-hour cruise departs at 7:30 AM from Kewalo Basin Harbor and offers stunning views of Diamond Head and the tranquil waters. Enjoy a unique glass-bottom experience that showcases the vibrant marine life below, all led by an experienced local crew. - Duration: 1.5 hours, daily from 7:30 AM to 9:00 AM - Includes coffee, pastries, and panoramic coastline views - Best suited for early risers, couples, and families - Departure from Kewalo Basin Harbor; arrive 30 minutes early

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.

Explore Oahu's most popular spots all in one day on this tour, including transportation to and from your hotel. Travel comfortably around the island in an air-conditioned coach or minivan as you pass by Diamond Head and North Shore Surfing Beaches. Make stops at the Dole Plantation, Kualoa Ranch and a variety of lookout points.

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.

Fit in a private kiteboarding, wind foiling, or wind surfing lesson while you’re in Oahu with this Kailua private lesson and learn the sport of your choice in class session that’s not packed with strangers. Plus, all your gear is provided for you, as well as an easy-to-use 2-way radio helmet.

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.

Watch the sunset over Oahu from the comfort of a 46-foot chartered yacht during a 2.5-hour private dinner cruise. With space for up to six passengers, this evening excursion is the perfect opportunity to celebrate an anniversary, share a special family experience, or take your annual girls trip to the next level. Enjoy a freshly prepared dinner, plus an open-bar with unlimited prosecco, beer, spirits, and non-alcoholic drinks.

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.

Enjoy the luxury of having your own 35-passenger catamaran for a private charter on the Pacific. Perfect for exclusive celebrations or a fun day with family and friends, this rental offers total freedom to create memorable experiences. Tailor your event to your vision, whether it's a wedding celebration, corporate gathering, or family adventure. Say goodbye to crowds and hello to personalized service on the water. - Host exclusive events like weddings, graduations, or reunions - Enjoy a private space for up to 35 guests, free from crowds - Customize your experience with personal touches and themes - Perfect for families, corporate gatherings, and special milestones

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on the front of the catamaran with 4 bean bag chairs as well as 2 small lounging nets on the back. Not only does Hawaiian Style have lots of room for lounging in the sun, but it also has plenty of seating in the shade as well. We have two coolers that we fill with ice for whatever food and beverages you choose to bring aboard. Stainless steel eco-friendly cups are also provided. We have Bluetooth surround sound which you can connect to and play your own music. All snorkeling gear is provided. We are a USCG inspected and approved company.