The truly unique culture of this legendary island is best experienced on the open water. Let Waypoints Annapolis® arrange the ultimate Key West vacation.
Key West is like no other destination in the world, combining history, natural beauty, and culture for a one-of-a-kind paradise. Ernest Hemingway, Tennessee Williams, Elizabeth Bishop, Robert Frost, and Jimmy Buffett, are just some of the famous locals.
Sightseeing, diving, fishing, watersports, golf, and shopping are just some of the adventures you can have shoreside. Your cruising adventure will feature pristine waters, remote islands, white sand beaches, and epic sunsets as only Key West can deliver.
Key West to Cuba
The Waypoints Annapolis® Key West charter affiliate is the premier US-based charter company offering full and legal yacht passages to Cuba. Set sail from Stock Island Marina Village in Key West, Florida bound for the famed Marina Hemingway, located just miles from Old Havana.
The staff has more experience operating legal travel to Cuba than any vessel charter company operating within the United States. With the recent changes in the US government and an ever-changing legal environment, we work very closely with the Office of Foreign Assets Control (OFAC), the Department of Commerce, and the United States Coast Guard (USCG) to ensure each person and vessel has complete clearance prior to leaving the United States and proper documentation for the vessel’s return to the United States. We have agreements with Cuban marinas and governmental organizations allowing our organization the safe and secure entry and docking of our vessels, completely compliant with the Cuba Visa visitors program.