Top Hawaii Sailing Tours - page 5

Choose your own adventure after you set sail from Maui to Coral Gardens on this cruise. You get three activities in one excursion: sailing, snorkeling, and whale watching. Spend your time in the water, relaxing on deck, or enjoying the buffet-style lunch and drinks. As a bonus, the tour also includes reef-safe sunscreen to protect you and the environment.

Enjoy your best day in Hawaii and discover a new Adventure! This sailing with snorkeling experience is amazing for you to relax and have fun.

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.

Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a spectacular Hawaiian sunset and the Friday Night Fireworks onboard a luxury private yacht.

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 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.

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 the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. This all-inclusive trip features top-notch amenities: premium snorkel gear, gourmet lunch, and post-snorkel beverages from our full bar, including beer, wine, and spirits. Our local, experienced crew goes above and beyond to provide personalized service, guiding you to the best snorkel spots along the Kona coast based on daily conditions. With ample space for personal belongings, towels, reef-safe sunscreen, and complimentary parking, we make your comfort our priority. Plus, our unique itineraries avoid crowded areas, giving you a more intimate encounter with Kona's vibrant marine life, including dolphins, tropical fish, and seasonal whales. Choose the Afternoon Ali’i Adventure for a truly unforgettable and one-of-a-kind ocean experience!

Adventure Awaits aboard our Fabulous 48' private yacht. Bring along your family and friends for a spectacular Hawaiian sunset on your private yacht. Get a chance to see whales, dolphins and sea turtles. Immerse yourself in a bucket list Adventure Today!

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.

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.

This 8 hour private tour includes a 5 hour custom tour of the island, and a 2.5 hour sail on a sailboat including swimming or snorkeling with turtles. You can pick and choose the stops on the island tour and go at your own pace. The sailboat leaves from the harbor in Waikiki and sails between the harbor and Diamond Head Crater, and stops at Turtle Canyon to swim with the turtles.

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.

Our sunset turtle snorkeling tour delivers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and unforgettable views in one trip. We reach Turtle Canyon quickly, giving you more time in the water to swim with Hawaiian green sea turtles in clear, warm conditions. Beyond snorkeling, enjoy kayaking, stand-up paddleboarding, sea scooters, and swimming—all included at no extra cost. The highlight is the timing. After your activities, relax on board as the Waikiki sky fills with vibrant sunset colors, with Diamond Head as your backdrop. The experience ends with a peaceful sunset sail, complemented by charcuterie and cocktails. With a friendly, attentive crew and beginner-friendly guidance, this tour is perfect for everyone—from first-time snorkelers to experienced ocean lovers. More than just a tour, it’s a memorable Waikiki experience you won’t forget.

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

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, and more. We offer this experience at a discounted rate to accommodate groups wanting to do private charters in the morning to celebrate lives, scatter ashes, and conduct meaningful ceremonies. Capacity: 49 Guests Maximum Juices, sodas, and water are included.

(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.

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

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.

Dive beneath the waves to explore Maui’s colorful fish, vibrant coral, and graceful sea turtles on this 6-hour snorkel excursion to Honolua Bay. Experience one of the island’s most popular snorkel spots with the help of a certified marine naturalist before heading to a second site for more underwater adventure. An included breakfast, barbecue lunch, and periodic sightings of wild dolphins help add to the experience.