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 on our Mauna Kea Sunset Cruise, departing from Kawaihae Harbor aboard Olohana — a 41-foot luxury powerboat designed for comfort and ocean adventure. Cruise the Kohala Coast as the sun dips toward the horizon, revealing sweeping views of...
Sunset Cruise with the Whales on our Power Catamaran
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 Signature Catamaran Sunset Sail
End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean and coastline as the sky transforms with vibrant hues of orange, pink and gold. Relax on deck with a tropical cocktail or glass of...
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...
Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii
Welcome to the only place in Hawaii where the spirit of ancient Hawaiian seafaring meets modern expectations on the pristine waters of the Kona coast. Immerse yourself in a unique and unforgettable experience as we invite you to join us for a 2.5-hour sail and snorkel...
Kona Catamaran Snorkel Sail with Lunch
Set sail from Honokohau Harbor aboard the spacious Spirit of Aloha for a 3-hr adventure along Kona's stunning coast. Cruise past lava rock cliffs and turquoise waters before arriving at a beautiful snorkel site teeming with marine life. Slip into the ocean to swim...
Kona Luxury Catamaran Yacht Snorkel & Sail
Discover the beauty of Kona's coastline aboard No Wiki, a spacious and comfortable sailing catamaran designed for relaxation and adventure. Cruise past rugged lava cliffs and turquoise coves while keeping an eye out for pods of Hawaiian spinner dolphins and other marine...
Kona Tradewind Catamaran Day Sail
Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails as you glide across the water, taking in panoramic views of volcanic cliffs, sparkling blue seas, and the Big Island’s...
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.