Waypoints Yacht Charters

Waypoints Yacht Charters is a premier yacht charter company based in Annapolis, Maryland, offering unparalleled sailing experiences across the United States and the Caribbean.

We specialize in providing luxurious and personalized charter vacations aboard new-model sailing catamarans and monohulls from leading manufacturers like Fountaine Pajot and Dufour. Our team of local charter specialists expertly guides you to the best sailing waters and hidden gems, ensuring unforgettable adventures in destinations such as the Chesapeake Bay, St. Petersburg, Florida, and the U.S. and British Virgin Islands.

Waypoints Yacht Charters distinguishes itself through its commitment to exceptional service, meticulous attention to detail, and deep local knowledge. We offer both bareboat and captained charters, catering to discerning travelers seeking a truly elevated and bespoke cruising experience. Our goal is to create lasting memories for our clients, connecting them with the beauty and tranquility of the sea.

Founded in 2021, Waypoints Yacht Charters has quickly established a reputation for quality and reliability, with a dedicated team of 8 professionals. We are proud to serve a global clientele seeking the ultimate in yacht charter vacations.