You've always been pretty comfortable on land. But there comes a time to leave your comfort zone. To learn how to thrive on the open water.

We're talking about taking a week, stowing away on a boat and sailing around the world. Or failing that, Chesapeake Bay.

Which brings us to Liveaboard Cruises at Chesapeake Sailing School, now putting you out on the water for two to seven days of glorious boating.

This falls somewhere between Sailing 101 (no experience required) and a camping trip on water. Your reservation secured, you'll want to gather six to eight sea dogs (or anyone else who doesn't mind referring to you as "Captain" for a long weekend) and make your way to Annapolis to meet your expert skipper, stock up on provisions (read: rib eyes and cabernet) and get to know your 44-foot vessel.

As you unfurl the canvas and set sail up the West River toward St. Michaels, you'll learn the finer points of wind-aided seamanship—tacking and jibing, navigating, right of way and repelling pirates with your flare gun. (Okay, maybe not that last one.) But it's not all edutainment: you'll have plenty of chances to swim or drop kayaks into the water to explore the Bay's various inlets. Oh, and pop a few cold ones at sunset.

We hear beer helps prevent scurvy.