Sea of Abaco, the Bahamas
Would-be captains won't find a better classroom than the Sea of Abaco, a massive lagoon in the Bahamas with sheltered conditions that are perfect for newbies. You'll encounter multiple outfitters in Marsh Harbour, where you can charter a private 40-foot cruiser with a captain and crew for around $5,000 per week. You'll live aboard and learn the basics as you cruise from island villages to deserted keys to one of the world's largest barrier reefs. If your goal is to become a bona fide skipper yourself, understand that this will be a working vacation — it'll take at least seven days, and in addition to your time on the water, you'll be cramming through three American Sailing Association courses. But you'll come away certified to bareboat — that is, charter a sailboat as the captain. Says Mark Gonsalves, owner of Cruise Abaco: "Many of our students return year after year and charter from us." And not just in the Bahamas. With bareboat certification, you can skipper a sailboat around the world.
Getting there: Daily nonstop flights leave from Fort Lauderdale, West Palm Beach, and Miami.