San Antonio v East/Southern Fl vs Savannah vs Charleston

We are sitting on two tickets from a COVID canceled conference that need to be used by the end of March. Looking for ideas to sway us in one direction from a couple of options.

We have on our shortlist:
San Antonio (which was to be our conference destination. So, hitting the River Walk)
East/Southern Flordia (My Dad winters in Cocoa Beach, so we usually go down to see him for a week every year or every other year. This time we were thinking of maybe also doing a drive then down to Key West.)
Savannah (My wife has wanted to go here for some time, mainly for the architecture and literary influences)
Charleston (everyone that goes there says "go there")

Any tips on must-sees, cons for these areas, etc, that I can then use to make a more informed decision?

Thanks in advance.

 

Was in Key West last month. Most of you know I lived down there 40 years ago, and man has it changed. Not good or bad, just different. My grown kids had an absolute blast there, and I had a pretty damn good time too. Savannah, Charleston...meh, you'll be bored in a day. If you want a real adventure, head over to the Dry Tortuga's for a day while your in KW.

 

The drive from Cocoa Beach to Key West will not be fun.

 

Dont drive...fly. Silver air has flights from MCO or FLL to EYW (Key West) for like $120 - 150 or so.

Book flight into MCO...see the are and drive to FLL or back to MCO and fly to EYW. Then fly home from EYW. OR drive up to MIA and fly home from there. 1 way rentals in that area of FL are usually not expensive.

 

We drove from Miami to the Keys and it wasn't bad at all. Take Card Sound Road for no traffic and interesting views instead of A1A into the Keys.

 

Meh you'll get bored in Key West in a day regardless of the Tortuga trip.

Explore Savannah then check out Tybee Island, then Hilton Head and then the 8th air force museum.

 

Savannah/Charleston can be lumped into the same trip.

 

Savannah is one our (wife and I) favorite destinations. Stay on the riverfront if possible. Tons of cool shops, bars and restaurants and you can carry your adult beverage from place to place while on the riverfront area. Cool architecture and tons of history there. Big-ass cargo ships gliding 100 feet away never fails to impress. Cool area.

 

Wife and I had always wanted to go to Savannah and once there (February) we walked a bunch and read A LOT! So much to see, however, it didn’t take us past two days if you’ve planned. We then drove to Charleston and Parris Island for a day and it was nice to see as well, just not more than a days worth though.

 

8th Air Force Museum! Holy shit. What a place. The sheer scale of the war effort was almost unimaginable. Here's a fun fact. The 8th had 26,000 men shot down and taken prisoner. Think about that. Thousand of scared, angry Americans running around the countryside, armed with .45s.

 

Nature and cultcha - Charleston
Diving and drunken debauchery-Keys
Food and theme parks-Orlando
A view of some mega yachts and cultcha- Savannah
Gunfire and Lerp- Jax
Last time in San Antonio we saw too many syringes and other junkie debris near the riverwalk but the food is awesome. The views outside of town are amazing