That was the question I posed to my wife after a long discussion about our long and short-term goals. Living in Washington, DC, so close to the historic Chesapeake Bay (one of the greatest bodies of water for sailing in the world), that was a natural next step. But that seemingly simple question, raised so many more; some far more complex. In general, sailing is more than a sport, it is a way of life. Regardless of whether or not one prefers coastal cruising, racing, on-shore, or off-shore "blue water" sailing, it gets in your blood and commands attention. This demand for attention is magnified, in spades, when one moves from crewing on someone else's boat or renting/chartering to boat ownership. The responsibilities increase by an order of magnitude, and the range of decisions you have to make are amazing.
This next set of posts will take you through that process, as it unfolded for us. I will cover the initial decision to move forward, and the logic that allowed us to make the decision. I will also cover finding and surveying a boat, decommissioning, commissioning, finding a marina, maiden voyage, boat ownership, hurricane prep, winterizing, and planning for the 2016 sailing season.