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 Anaehoʻomalu Bay and Honokōhau 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.

Kona-Kohala Coast Sunset Sail by Catamaran

341
from $152.55

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 ...

  • 1.5 hours
  • Free Cancellation

Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani

35
from $117.76

Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. This 1.5-hour journey from Honokohau Harbor offers a chance to bask in the sun and enjoy the ocean breeze while taking in the breathtaking views. ...

  • 1.5 hours
  • Free Cancellation
Likely to Sell Out

Kealakekua Snorkel and Sail Adventure

631
from $177.65

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast.  Scan the horizon for dolphins and whales (seasonal) from our shaded cabin or sunny splash nets.  Snorkel calm waters and lush coral gardens using our ...

  • 4 hours
  • Free Cancellation

Afternoon Sail & Snorkel to the Captain Cook Monument

671
from $136.19

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 ...

  • 3 hours
  • Free Cancellation

Pau Hana Sunset Cocktail Cruise

48
from $165.00

Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed catamaran. This cruise includes unlimited soft drinks, tropical juices, beers, wines, cocktails and a variety of appetizers.. Great fun -- great ...

  • 2 hours
  • Free Cancellation