I never thought of sailing as roughing it, either. On the contrary it's more like travel: something to celebrate, even close to home.

You're in the epicenter of boatings highest expense center, and you know things get cheaper - going either way- as you chose your itinerary.

Todds idea is a good one and you know that as dockage options dwindle, anchorage options abound in most areas to your North. Good options, not open roadsteads. Places you can settle for a day, or even a week.