Author: Nathan Knight

Sunset Watersports and Barefoot Billy’s Join Forces

Two Key West Icons, One Local Family. 

KEY WEST, FL (January 2026) – Sunset Watersports, a cornerstone of the Florida Keys watersports community for over 40 years, is proud to announce the acquisition of Barefoot Billy’s. This union brings together the two most storied names in Key West adventure, creating a partnership built on shared history, mutual respect, and a deep love for the water. By combining their expertise, these two pioneers are doubling down on their commitment to providing the premier, authentic island experiences that only a home-grown company can deliver.

Celebrating Our Roots: The Strength of Independent Ownership

As the tourism landscape in the Florida Keys continues to evolve and attract global interest, Sunset Watersports and Barefoot Billy’s remain dedicated to their identity as locally owned and operated businesses. We believe that being “independent” isn’t just a business model, it’s a commitment to the community. It means our management is on the docks every morning, our captains are our neighbors and our profits stay right here in the Keys to support local families and local initiatives. By joining forces, we are ensuring that the heart of Key West’s watersports industry stays rooted in the very community that helped build it.

The Sunset Watersports Legacy: 40 Years of Innovation

The story of Sunset Watersports began in 1984. Founded on a vision of making the ocean accessible to everyone, Sunset was the original pioneer of commercial watersports in Key West. Starting with a single boat on Smathers Beach, the company didn’t just join the industry, it helped shape it.

Over the last four decades, Sunset has been a leader in maritime innovation, most notably through the creation of the world-famous “Do It All” watersports adventure. As the oldest existing parasail company in the United States, Sunset’s 40-year anniversary is a testament to the Welter family’s enduring dedication to the island and the generations of visitors who have made memories on their decks. Sunset Watersports now offers premier trips and tours for all of the top things to do in Key West such as sandbar charters, reef snorkeling trips, dolphin tours, sunset dinner cruise, sunset sailing cruises, parasailing, jetski tours, kayak tours, golf cart rentals and boat rentals.

The Legend of Barefoot Billy’s: An Island Original

Just a few years after Sunset began its journey, another legend was taking shape. In 1988, “Barefoot Billy” established himself as the island’s most trusted expert on beach life. But Billy saw an opportunity for something greater. In 1992, he launched a Key West institution: the Barefoot Billy’s Island Jet Ski Tour.

Billy was the first to envision a 26-mile guided jet ski tour circumnavigation of the island, offering a perspective of Key West that was previously unreachable. From its roots in high-end resort partnerships at the Casa Marina and Marriott Beachside, Barefoot Billy’s grew into a boutique powerhouse. Known for its curated “concierge” feel, the brand has always focused on personal connections and the “home-grown” spirit of adventure. Now Barefoot Billy’s is locally known for incredible snorkeling, parasailing, sandbar charters, golf cart rentals and more.

Our Shared Commitment: A Home-Grown Future

The unification of Sunset Watersports and Barefoot Billy’s is a celebration of two legacies coming together to better serve our guests. Our mission is to maintain the unique, personal touch that has defined both brands for decades.

• A Personal Touch: We avoid the “one-size-fits-all” approach. Our experiences are designed by locals who know these waters intimately.
• Community First: We are proud to provide stable, rewarding careers for hundreds of Key West residents, ensuring that the wealth of our industry supports our local schools, parks, and people.
• The Best of Both Worlds: Guests can now enjoy the “Legacy of the Original” at Sunset and the “Boutique Resort Vibe” of Barefoot Billy’s, all under one trusted local umbrella.

When you join us on the water, you aren’t just a passenger; you are part of a 40-year Key West tradition. We invite you to experience the passion, history, and home-grown hospitality that only the island’s original pioneers can provide.

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