A sailing trip that lets you play captain
There's something liberating about the thought of taking to the high seas, with the wind whipping through your hair, the land at your back, and Captain Ron at your front, failing to properly define what he meant by "guerrillas". Get the training to ditch the captain, with Blue Water Sailing School.
Providing a one-week "hands-on" adventure vacay on the water, BWSS is an all-inclusive, no-experience-needed live-aboard sailing cruise aimed at teaching you the nuts and bolts of coastal sailing in a relaxed, beautiful setting, that results in you being certified to charter a boat with friends/family anywhere across the globe -- although convincing friends/family that that's the case is a different story, no matter how laminated the certificate. Here's how the odyssey at sea unfolds: after flying into Ft. Lauderdale (or St. Thomas if you're feeling a little more frisky/wealthy), you'll board a 40-foot sailboat, snag a berth, meet your crewmates/instructor, and prep/provision your new home; after a heavy meal/drinking at the marina, you'll cast off the lines the next morning, point toward the horizon, and head to the Keys, and if you're worried you've forgotten the Dramamine, you'll find out soon enough. From there, you'll channel your inner Matthew Modine and spend days learning on-the-water sailing skills: setting sails, driving the boat, reading charts, and dropping anchor, not to mention learning how to maintain/repair the boat's systems, tie a solid bowline, and properly trim your jib, which you should really think hard about doing, because it usually grows back waaaay thicker.
Because no one wants to learn all the time, late afternoons/evening are yours for a little extracurricular R&R, swimming, and snorkeling after anchoring; on the last day you'll make it all official by taking the certification exam, which'll prove that you actually learned something, and that no, you didn't mean what you wrote in your diary about "Captain Mo-Ron".