Skip to content
Hawaii-based. Sharing the islands since 2006. Plan · Explore · Experience · Hawaii

Explore Hawaii.Island time, well spent.

Hawaii tours & activities

Aloha. Where to?

Choose your island. Let the good days begin.

Explore all activitiesOcean days, luaus & island adventures

Trade Winds off Kona

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.

From our home in Hawaii

Memories You’ll Bring Home.A little aloha shared.

From your first morning on the water to an evening beneath the stars, we hope you find activities that stay with you long after your trip. To-Hawaii.com is created by a small local Hawaii-based team, and every booking made through our links helps support the work we do – exploring the islands, taking our own photos, and sharing the places, stories and details we think are worth knowing. We’re glad to be a small part of your time in Hawaii and hope you leave with plenty of good memories to take home.

Mahalo for letting us be a small part of your Hawaii adventure.

Hawaii tours & activities

Search activities