25 years have past since I have stepped onto a sailboat. The last time, I acted as overly enthousiastic 12 yo. crew sailing with family in Sweden and some of the bigger Bavarian lakes.
Well, a lot of time has passed and now I have finally the time, funds and (hopefully) passion to do something more productive with my free time than spending weekends in front of the TV or in the bars in Philadelphia.
I have signed up for the ASA101 class (on the Delaware, yuk, but that's the most convenient place to get started), hope to get my ASA103 shortly after that and then, of course, want to go sailing! Initially, I thought it would be a good idea to look for my own boat (preferably a 25"-30" cruiser, like a 20-yo. affordable Catalina 25), but I think I might be better off feeling the waters first by chartering for the first year to see, if the enthusiasm "sticks".
I live between Philadelphia and Wilmington, so the distance to get to the nearest port is a problem. My best bet is probably a charter from Havre De Grace, but I realized that you have to motor for about a hour until you even can set sails and I am questioning, if that HdG is a good starting point for day trips or, if I should rather travel more south to the Annapolis area or the Eastern part (Easton, MD) of the Bay.
The other option would be the Jersey shores and I am aware that there's probably a huge difference between sailing in the Bay and coastal cruising, but I think for starters
the Bay looks just more attractive (and easier?) to learn, however I do realize that the Bay, especially in the far North, is relatively shallow. And there is probably a lot more "to do" as far as destinations compared to coastal cruising, where you're also more dependent on wind direction.
Does anyone have any advise for the best areas in the Bay to get started? I am looking primarily for daysails to practice. Overnight and weekends can come later, because I think that you need at least the "Bareboat chartering" course to charter.