Warm island chains in the Caribbean anchor much of the region's sailing reputation, with reliable trade winds and a high concentration of sheltered anchorages within short distances of each other. A rockier coastline further north offers a considerably different, colder sailing tradition.
The destinations on this list range from warm-water Caribbean routes built specifically around charter tourism to colder coastal sailing further north with a longer, more traditional maritime history. Conditions and required experience vary considerably between the two.
Booking well ahead for Caribbean peak season matters considerably, since the best boats and routes fill up months before winter arrives. Local charter companies can advise on which anchorages stay quietest. Packing reef-safe sunscreen also matters considerably given the sensitivity of the surrounding marine environment.
