Are you sure you want to be that far north in one of the coldest months?
OP is from Virginia, so it probably won't seem that cold to them! :-)
Pensacola has lots of history and close enough for day trips to Mobile, Biloxi, etc. depending on your particular interests. Not sure what condos are available in Pensacola since we stay at the beach, but lots of condos available at Pensacola Beach on vrbo.
I agree with some of the other reviewers. February is the coldest month up here, so unless you are use to being outdoor in very cold weather, you may be a bit disappointed. But on the positive note it certainly will not be very crowded. One person suggested Pensacola. There is a lot of history, and not far from Biloxi and Mobile. They also have one of the best Air Museums in the country in P'cola and no one is ever disappointed to go there.
On the other hand, if you go to Panama City, I do not think there is as much in the way of Historical things. If you are that way, check out Eden State Park. Panama CIty is right next to a new and upcoming development off of 30A. (you can look what all is there on line) While technically that is Beach towns, a lot of people travel to the Panhandle these days just to visit 30A. There will be a good number of restaurants that way. Panama City is about 30 minutes from Destin. Again, not a lot of culture since it is more of a beach town, but you may find some good places to eat.
Either one of those locations, you would still be within an hours drive of FWB if you wanted to come here. They do have Eglin and Hurlburt, but outside of that, you will struggle to find good food and a whole lot of cultural things. So I would steer clear of FWB, unless you would like middle ground between P'col and Panama City.
And if you haven't spent a lot of time on our beaches, you really should plan to go to at least one restaurant that offers you a good view of our sugar white beaches and emerald green gulf at least once. These restaurants will usually be closed in during the colder months, so no worries about being too cold while eating. It is a beautiful view . Hope you enjoy yourself.
Given I am from Maryland (north of VA) I would find the panhandle too cold int he middle of winter for me anyway. I know Canadians find it OK, but they have to deal with much colder weather than MD/VA.
It all depends on what kind of winter we get, a cold one or a warm one. Last year, Feb was warmer than march for instance.
There are a lot of history locations in the Panhandle. If you are wanting to see a broad range, Fort Walton is a good jumping off point.
One of my favorite things to do is the lighthouse run. While the official light house challenge is not happening, because they are relocating the Cape San Blas house, you can still visit them on your own. It shows a broad history of lighthouses with several different types and their importance in our history. More info: http://wikitravel.org/en/Florida_Lighthouses
Pensacola is rich in history. Between Fort Pickens, Fort Barrancas, the Aviation Museum will keep you busy a few days. The Wentworth Museum is fun, too and downtown Pensacola has a ton of restored homes in their historical district. Because of the variety of influences, the architecture is fun. It is a good jumping off point if you would like to head to Mobile (which has the battleship). Pensacola is really the only thing that will take several whole days, the rest can be combined into day trips.
Milton has a fun old downtown with little shops and the best bakery (Milton Bakery) in the panhandle. The West Florida Train museum is interesting too http://www.wfrm.org/. It's a small town, and if you like that, it's fun. Crestview also has a historical downtown with little shops & Desi's is a great buffet to get home southern cooking during the lunch hours on weekdays. Coney Island is also a hamburger place on Main that is fun that's been serving for sixty years. Defuniak Springs has a sinkhole lake that is in the middle of their historic district that you can walk the path around, and makes for an enjoyable afternoon stroll if the weather is good. They have a cute B&B there too. The Chatauqua Assembly is in January (if your dates are flexible) florida-chautauqua-center.org/assembly_2014/…
Fort Walton Beach has the original Schoolhouse & Indian Mound Museum, which will keep you busy about an hour. The Armament Museum at Eglin also has recent history (WWII +). There are also two small museums one in Valparaiso http://www.heritage-museum.org/, and one in the north end of the county in Baker. If you are passing through Valparaiso, The Front Porch is an amazing breakfast place - they also have great lunches. Highly recommended. http://www.auntmarthasbedandbreakfast.com/ is a good place to stay if you're not about condos & hotels.
More than Panama City, the northern parts of the eastern end of the panhandle has more historically centered places, like Marianna (which also has Florida Caverns - http://www.floridastateparks.org/floridacaverns/) and Tallahassee. But Cape San Blas & Apalachicola are nifty. Here is a good, succinct linking to most places in the Panhandle http://phonl.com/historical.cfm.
If you are around Eden State Park in Walton County, the E.O. Wilson Biophilia Center is fascinating. Their hours open to the public are limited, so check them out if you are interested ahead of time.
Not knowing what type of history you like, That's the best I can do. Hope some was helpful.Edited: 1:08 pm, November 25, 2013
Sorry. I should have said, if you find yourself in Baker, the Gator Cafe is good food.
And, I should define good food. Home cooking, decent portions, and good seasoning.