Top Hawaii Sailing Tours - page 5

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.

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.

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.

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!

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.

Experience Waikiki like the celebs do—from aboard a private yacht. With your captain at the helm, you’ll glide toward Diamond Head at sunset, you and your crew basking in the views, catching splashes of dolphins and whales in the distance. As the sun sets, the city lights begin to glow, and the views only get better and better.

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.

Spend a leisurely afternoon sailing aboard the widest and most stable and luxurious catamaran in Maui, where your adventure takes you to the stunning waters of Molokini or a secret turtle sanctuary. Enjoy hand-shaken Mai Tais and delicious island-style pupus as you glide over the calm waters, led by a captain who knows the best spots. Experience the beauty of Maui, whether at the crater’s edge or hidden coastal treasures, while soaking in the sun and the vibrant atmosphere on this relaxing cruise. - Relax on the widest sailing catamaran in Maui - Discover the best water spots, from Molokini to turtle sanctuaries - Enjoy hand-shaken Mai Tais and island-style pupus onboard - Ideal for those looking to unwind and experience Maui's beauty

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.

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!

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.

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

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.

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

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.

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

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.