pensacola/destin/panama city is the best sailing and anchoring I have ever done (admitedly add most of the s.east lakes, charleston, and off key largo and that is my limited sailing resume.
Third year I had my 26s I went through blueboat envy...still have it to a degree. One day, perhaps, if I can save the money... But more and more, I see the advantage of being able to drive to and sail to many destinations. Like another post wrote better to cruise today in the boat you have. If a longer trip, I try to find anchorages every couple of days near a state park...lots of walking trails, free hot showers... Just went to lake murray. The lake- good sailing, lots of boats to play with, and lots of islands to anchor/camp on- and the island state park there makes for a great mix of good sailing and nice amenities when in a spartan boat.
"A speck on the sea" is a great read for those thinking about blue water in a small boat, or those who want to armchair explore courageous, on the edge of absurdity, wild things some folks do.