Top Hawaii Sailing Tours

The Au’au’ Channel is best known for its concentration of humpback whales. Hop on a boat in Maalaea Harbor to sip on a drink and spend time in the whales’ natural habitat. Your guide not only offers a trained whale-spotting eye but ensures you learn about the animals’ behavior and migration patterns. Don’t forget your camera: Lucky visitors get the chance to see the whales breaching in the open water.

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.

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.

Add some more outdoor adventure to your Maui itinerary with this Koa Kai whale watching trip at sunset. Get the chance to see humpback whales up close as they visit Maui to birth their young. Relax on deck, admire the natural scenery, and listen whale songs through the onboard hydrophone. Plus, you can enjoy alcoholic beverages and snacks throughout the journey.

(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.

Step aboard a boat and experience whale watching like never before. On this special cruise, see humpback whales in their natural habitat and hear them too. With a partnership with the award-winning immersive experience “Sounds of the Ocean,” be immersed in the hauntingly beautiful songs of the humpbacks as they echo through the Pacific. For twenty-five unforgettable minutes, everything else fades away and you’re transported into the whales’ world of sound with onboard hydrophone technology and personal headphones. Along the way, expert naturalists will share the classic PacWhale Eco-Adventures experience you love — breathtaking encounters, small group interpretation, and fascinating whale behavior — but with a special focus on the incredible role sound plays in the lives of these ocean giants. Discover how whales communicate, court, navigate, and even share cultural traditions through song. Learn about the growing challenges of noise pollution in the oceans.

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.

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. Our warm, relatively shallow and protected waters make an ideal location for the humpbacks to mate and give birth to their calves. These whales are known for their acrobatics, and are often seen fully breaching out of the ocean! This charter is a seasonal opportunity, available from December 15th to March 31st annually.

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

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.

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 850 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.

Indulge in a personalized sailing experience aboard the luxurious 51-ft Lagoon catamaran, No Wiki. This private charter offers an unforgettable journey along the stunning Kona Coast, where you can snorkel vibrant reefs or simply relax in comfort. With a professional crew dedicated to your enjoyment, your itinerary is fully customizable. Enjoy complimentary drinks and catering options for an enhanced experience. - Private luxury charter for up to 6 guests - Explore pristine snorkeling spots and scenic views - Comfortable shaded seating and onboard restrooms - Upgrades available for extended adventures to Kealakekua Bay

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 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

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

Waikiki transforms into a vibrant spectacle on Friday nights, and the Friday Fireworks Cruise offers a unique vantage point to experience this magic. Departing from Kewalo Basin, enjoy a 90-minute cruise with stunning views of the Waikiki skyline and a front-row seat to the fireworks display. Sip on light refreshments as you soak in the atmosphere and the ocean breeze, all while avoiding the crowded beaches. Perfect for date nights or special occasions, this cruise ensures a memorable evening in paradise. - 90-minute cruise with offshore fireworks viewing every Friday at 7:00 PM - Depart from Kewalo Basin Harbor with easy access and no parking hassles - Light refreshments included; BYOB allowed for a more personalized experience - Suitable for all ages; children must be accompanied by a guardian

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