Try matching the kind of sailing you like to do with the prevailing conditions in the areas that you’re considering. For example, if you have a distinct preference for sailing in light or heavy air, read or ask about average windspeed during the time frame you’re considering. Try to match your sailing abilities with what will be required of you. Most popular charter spots offer easy, line-of-sight navigation, and charter companies provide good charts and guidebooks as well as a thorough orientation by knowledgeable company staff. Some locales, such as the British Virgin Islands, have moorings for pickup in many harbors, so anchoring isn’t always necessary.
When considering where to sail, also evaluate what each area has to offer in the way of après-sailing activities. If you like snorkeling on coral reefs and rum punch in a tiki bar after a day of hot-weather sailing, consider the Caribbean or South Pacific. If the idea of spending time in
Margaritaville appeals to you, try South Florida or the Bahamas. If you like whales and wildlife, try the Pacific Northwest. If culture, ancient civilization, and delectable ethnic cuisine interest you, consider the Mediterranean and the Aegean and Adriatic Seas.
When choosing a vacation spot, take into account the amount of time you have, how much sailing you need to do an area justice, and travel time on each end of the trip. Spread out charts of your charter area on the living room floor, grab a glass of wine, and have some fun planning where to go, plotting distances to see what you can reasonably accomplish in the time allotted. Then confer with charter-company representatives; they’re well versed about a myriad of details, frequently asked questions, and different itineraries in their areas. They—and their websites—can confirm how long you’ll need to visit, at your preferred pace, the places that appeal to you.