
Tim Montgomery
Captain Tim Montgomery
Originally from St. Louis, Missouri, Captain Tim began his career as a chef, working in kitchens and aboard vessels around the world. His passion for the ocean truly took hold during three years with National Geographic’s expedition ships, sailing the coasts of North and Central America. That journey eventually led him to the Virgin Islands, where he fell in love with the vibrant culture, community, and turquoise waters of St. Thomas.
Over the years, Tim has captained yachts throughout the U.S. and British Virgin Islands and the Lesser Antilles, discovering hidden coves and local favorites few visitors ever see. He holds a USCG Master’s License and STCW 95 certification and has spent more than 3,000 days at sea.
Tim prides himself on creating a relaxed, personalized experience for every guest. Rather than following rigid itineraries, he reads the mood of each day and tailors the adventure accordingly. Whether guests are looking for secluded beaches, world-class snorkeling, quiet sunsets, or legendary beach bars, he knows just where to go.
Known for his easygoing leadership, knack for great cocktails, and occasional guitar session at sunset, Captain Tim is dedicated to making every charter aboard feel personal, memorable, and true to the spirit of the Caribbean.

































