With first rate charts and other navigational aids, the Florida Keys are an ideal cruising ground for all sailors, regardless of experience. The famously warm, clear waters of the Keys are a snorkeler’s paradise—shipwrecks and coral parks are plentiful—and secluded beaches number in the hundreds. If you crave terra firma, you can always stop at Key West for a nightcap at Sloppy Joe’s, a favorite hangout of writer Ernest Hemingway. One full day’s sail west of Key West brings you to the Dry Tortugas, home to Fort Jefferson, which dates back to Civil War days. This is a popular sailing route. If you feel like you’re off the charts, anchor at any harbor and ask the nearest boater for directions. Thankfully, yachting is no longer a sport only for the affluent. Florida Keys Bareboat Charter Company in Marathon bareboat charters a 27-foot Catalina for a cost of $899 per week (7 days/6 nights).
Steve Jermanok As a columnist for National Geographic Adventure, adventure travel expert at Budget Travel, and regular contributor on outdoor recreation for Outside, Men’s Journal, Health, and Sierra, Steve Jermanok has written more than 1,000 articles on the outdoors.He’s also authored or co-authored 11 books, including Outside Magazine’s Adventure Guide to New England and Men’s Journal’s The Great Life. His latest book is Go Now! Put Your Life on Pause and See the World. He’s currently an adventure travel expert at Away.com and blogs daily at Active Travels.