The Captains & Crew - Palm Tree Charters

About Palm Tree Charters

Founded in 2005 by John and Sue Brandi, Palm Tree Charters quickly became a beloved staple for both visitors and locals on St. John. Through their dedication and hospitality, John and Sue built a successful business known for creating unforgettable boating experiences.

In 2014, Captain John Brandi retired, passing the helm—and the iconic Palma Bella—to Jimmy and Bridgett Key. Since then, Palm Tree Charters has continued to grow. Now with their fleet of 4 boats, Palm Tree Charters has a comfortable boat for you, whether you are looking for luxury, speed, or a budget friendly option.

Today, Jimmy, Bridgett, and Crew are dedicated to ensuring your day on the water is as relaxing and fun as it is memorable. From start to finish, you’ll enjoy top-notch service, expert guidance, and the warm, friendly atmosphere that has made Palm Tree Charters a trusted name in the Virgin Islands.

Captain Jimmy

Jimmy Key

Meet Captain Jimmy Born and raised near the scenic Tennessee River in West Tennessee, Jimmy has always had a deep connection to life on the water. After a successful career in computer programming and business management, he decided to follow his passion for boating and adventure, earning his U.S. Coast Guard 100-ton Master Captain’s license. In 2014, Jimmy and his wife Bridgett made the leap to island living, settling on the beautiful shores of St. John. As the captain of Palm Tree Charters, Jimmy combines his love for the sea with his wealth of knowledge about the islands and their rich history—enhanced by colorful tales passed down from the legendary Captain John. Whether you’re seeking a relaxing day on the water or a journey filled with stories and island lore, Captain Jimmy is ready to make your experience unforgettable.

First Mate Bridgett

Bridgett Key

Meet Bridgett Bridgett’s journey began in central Mississippi, where she spent her early years, before moving to Tennessee during high school. With a background in restaurant management and real estate, her most cherished role was being a full-time mom—a career she considers her greatest accomplishment. A lifelong dreamer of island living, Bridgett was inspired by a dear friend’s advice: “Don’t wait until it’s too late—come now.” Taking that wisdom to heart, she and Jimmy made the leap to St. John in 2014, embracing the Caribbean lifestyle. Now, as part of Palm Tree Charters, Bridgett thrives on sharing her love for the Virgin Islands with every guest. Whether she’s guiding you to hidden gems or helping you soak up the island magic, her passion for the sea and the islands shines through in every moment.

1st Mate Ayla

Ayla Martin

Meet Ayla Hi! I’m Ayla. I grew up in upstate New York, but on New Year’s Day in 2019, I decided to take a leap of faith, bought a one-way ticket to St. John, and never looked back. Living here means no more icy windshields in the morning, but what truly captured my heart is the incredible, close-knit community—it felt like home from the very beginning. Every day on the water feels like a gift, and I love sharing the magic of St. John with our guests. Whether it’s guiding you to our favorite snorkel spots or venturing out to explore the breathtaking North Sound, I’m here to help make your experience unforgettable. When I’m not on the boat, you’ll find me soaking up the sun at the beach, hiking scenic trails, crafting jewelry, or diving into the world of plant medicine. I can’t wait to welcome you aboard—your day with Palm Tree Charters will be a memory you’ll treasure forever!

Captain Landry

Landry Boysen

Meet Landry Captain Landry brings a passion for the sea and years of expertise to Palm Tree Charters. As a U.S. Coast Guard-certified 50-ton captain, he has a deep love for being on the water and making every trip a safe, exciting, and unforgettable experience for his guests. When he’s not at the helm, Landry enjoys exploring beneath the waves as an avid scuba diver. His commitment to the community is just as strong as his connection to the water—he proudly serves as a volunteer with St. John Rescue, offering his skills to help keep the island safe. Whether you’re looking for hidden snorkeling spots, scenic island views, or simply a perfect day on the water, Captain Landry’s knowledge, enthusiasm, and dedication ensure every guest leaves with incredible memories.