Big Island Sailing
Set sail along the Big Island's breathtaking coastlines and discover the beauty of Hawaii from the ocean. Whether you're cruising at sunset, snorkeling in crystal-clear waters, or simply enjoying the ocean breeze, Big Island sailing tours offer a memorable experience for every traveler. Departing from locations like Anaeho'omalu Bay and Honokohau Harbor, catamarans like the Spirit of Aloha, Honi Olani, and Kona Style provide comfortable and scenic journeys along the Kona and Kohala coastlines. Along the way, you'll have the chance to spot playful dolphins, sea turtles, and even humpback whales during the winter season. Snorkeling adventures often include visits to pristine sites like Kealakekua Bay, home to vibrant coral reefs and the historic Captain Cook Monument.
Many sailing tours combine relaxation and adventure, offering opportunities to snorkel, swim, or simply unwind with a cocktail while admiring a colorful Hawaiian sunset. With friendly crews, beautiful vessels, and spectacular ocean views, Big Island sailing is an unforgettable way to connect with the natural beauty of Hawaii. Whether you're celebrating a special occasion or just looking to experience the magic of the Pacific, a sailing tour promises a highlight of your Big Island vacation.
Featured Big Island Sailing Tours
Mauna Kea Signature Sunset Coastline Cruise
Unwind in true island style with our laid-back Sunset Coastline Cruise, departing from Kawaihae Harbor aboard our sleek, custom-built RHIB (Rigid Hull Inflatable Boat) – Olohana. This evening escape is the perfect way to end your day on the Big Island — with...
Sunset Cruise with the Whales from Kawaihae Harbor
Combine unparalleled views of the Hawaiian coastline from this well-appointed power catamaran with the biggest guests of all -- the Humpback Whales -- and you have perfect way to begin your evening in paradise! This cruise includes a assorted appetizers and a...
More Big Island Sailing Tours to Inspire Your Trip
Afternoon Sail & Snorkel to the Captain Cook Monument
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise...
Deluxe Sail & Snorkel to the Captain Cook Monument
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters and vibrant reef of the marine...
Waikoloa Signature Catamaran Sunset Sail
Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamaran. Catch the moment the sun slips below the horizon. You may even see the green flash. Board from Anaehoomalu Bay (A-Bay) to sail, enjoy and relax. The custom-designed...
Afternoon Sail & Snorkel to the Captain Cook Monument
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters...
Kona Catamaran Sunset Sail
Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. Catch the moment the sun slips below the horizon...you may even see the green flash. Enjoy the blue Pacific Ocean and maybe catch a glimpse of wildlife at play. Enjoy...
Afternoon Ali'i Adventure
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...
Kaimana Crafted Sunset Cruise
There's no better place to watch the sunset than on the Kona waters. You may even be able to witness the mysterious green flash! This setting is a beautiful location to capture your special even or occasion.
Kona Catamaran Snorkel Sail with Lunch
Hop aboard and enjoy the comfort of the 53-foot sailing catamaran with ample seating and shade. Enjoy the beauty of the Kona coastline, take in the amazing wildlife and refresh with a swim and snorkel. Snorkel vest, fins and in-water assistance from expert crew are...
Kona Tradewind Catamaran Day Sail
Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunning Kona coastline. This relaxing daytime cruise is perfect for spotting Hawaii’s incredible marine wildlife—keep your eyes peeled for dolphins, sea turtles, and,...
Luxury Catamaran Yacht Snorkel & Sail
We take you on an unparalleled yacht to experience the beauty and grandeur of the Kona coast and its most bejeweled underwater treasures. Every guest is provided with use of an inflatable snorkel safety vest and snorkel gear including prescription masks if needed....
Frequently Asked Questions
Where do most sailing tours depart from on the Big Island?
Most sailing tours depart from Kailua-Kona Pier, Honokohau Harbor, or Anaeho'omalu Bay near Waikoloa on the Kohala Coast.
What types of sailing tours are available?
You can choose from daytime sails, sunset cruises, snorkeling sails, whale watching tours (seasonal) and private charters.
Do I need sailing experience to join a tour?
No experience is necessary. All tours are crewed and include safety briefings and onboard guidance throughout the trip.
What should I bring on a sailing tour?
Bring sunscreen, sunglasses, a light jacket, a camera and swimwear if your sailing tour includes snorkeling.
Are food and drinks included on sailing tours?
Many sailing tours include beverages and light snacks or meals, especially during sunset or dinner cruises. Check the specific tour for details.