The Journey may be at an end Roger, but there are always a few little "side trips" I would definitely go down to Fernandina Beach. The anchorage has excellent holding and the marina is very accommodating at their dinghy dock (inside the marina). It is so close you will find the landscape from the anchorage is much like St Mary's, but the town has something to offer in terms of history.
And that is as far as I would go into Florida. This from someone who lives in Florida, but not East coast. The ICW from Fernandina to Jax is nothing special and I would not bother unless you wish to visit your friend. Even then I would be hesitant. St Augustine is very nice, but again you would be faced with getting there in the ditch. As for going offshore. That is what I do. But if that is not your style then hang out where you are comfortable in South GA and maybe very North FL.
And that is as far as I would go into Florida. This from someone who lives in Florida, but not East coast. The ICW from Fernandina to Jax is nothing special and I would not bother unless you wish to visit your friend. Even then I would be hesitant. St Augustine is very nice, but again you would be faced with getting there in the ditch. As for going offshore. That is what I do. But if that is not your style then hang out where you are comfortable in South GA and maybe very North FL.