Re: Boat recommendations for a Newbe
The small boat idea is a good one to learn how to sail. Even a Sunfish will do for starters. I learned on a Lightning which would IMO be a good choice: trailerable, a real sailboat with a headsail, not overly expensive. On the other hand, if you wanted to go right to a keelboat, an A30 or a Triton might be boats to think about. They would carry you south with no problem, eliminating the need to switch later.
Alberg 35: With a philosophical flourish Cato throws himself upon his sword; I quietly take to the ship.