Offering year-round sunshine and thousands of uninhabited islands to explore, chartering a yacht in the Caribbean is never far from the top of ultimate wanderlust during the chilly winter months. That said, the best time to visit is from November to March, when Europe and North America are at their coldest. The warm and clear waters, less salty than the rest of the Atlantic, are a yachting paradise, with more islands than you can visit in a lifetime.