I stayed at Hampton Inn on St. Aug beach. It's a ways out from the historic part.

I would book ahead. Winter is the busy season in FL. In my opinion, there is more to see and do if you stay in St. Augustine, not St. A beach

So, if I'm understanding-----
emalloy, The ponies are on Assateague Island in the winter, but we would stay on Chincoteague, right?
nfmeredith & suewoo----to see the sights well stay in St Augustine, rather than on the beach, and we will book ahead.
Thank you all

Hi everyone, We thank you for so many helpful comments.
We finalized our plans and want to see what you all think of it.
Since we haven't see any of these areas, feel free to send along and tips.
Leaving Connecticut on Feb 1
First two nights in Chincoteague.Staying at Hampton Inn on Main st.Thought that would be a good place to stop (7 or 8 hour drive).We'll poke around there for the next day, maybe see the ponies, then on to--
Next 3 nights in Charleston. staying at King Charles Inn on Meeting St.
Then on to St Augustine. 3 nights at Bayfront Inn on Avendia Menendez.
From there we will cross over to the west coast of FL to visit friends in St Pete. We'll drive thru (look around/ have lunch)in Mt Dora, because friends told us that we might like it there.
After visiting for a few days on the west coast we'll head to our place in Hollywood, FL.
For the trip home, we have scheduled 3 nights in Savannah GA,(maybe a drive thru Amelia IS?)Mrs Wilkes Dining Room in Savannah has been recommended to us so it's on the list!
Then up to Greenville SC (been there before)to explore some more, because we have been considering retiring to that area.
Then we'll head back to CT.
Any sights/ good restaurant recommendations for any of those locations?
Thanks again for any and all advice.
K.

Great itinerary!

Greenville was featured in the New York Times travel section on Sunday, December 7, 2014. My sister and brother in law live right downtown, and it is very, very pleasant.

Great idea about Greenville. It is a great town with a LOT going on. Don't miss the museum and its Wyeth collection.

Sounds like a great plan.

If either of you is 65 and a US citizen, get a senior National Parks pass at Chincoteague when you enter the park. It is good for a lifetime and lets everyone in your car into all National Parks free.

For the trip home, consider heading over to the Blue Ridge Pky/Skyline Drive and then linking to I-81 to 84 for a different route and one that misses NYC.

Grreat info--We'll look into all of that!
Another question about toll roads. We do not belong to any toll programs as of yet.
I see that the Mass. EZpass will cover us from CT to NC, but do we need to purchase others for NC, SC, GA and FL? Isn't there one that would cover all?
Thanks

Been Doing some research--I think that we can get EZ pass to work from Mass thru NC--and Sun Pass to work from NC thru FL----am I right?
Not sure about SC though.