They don't all have to be big cities, right? I just spent an awesome month in two very different parts of Florida. Lake Wales and Saint Augustine are both historic Florida towns with tons of character that offer unique experiences. Saint Augustine is a coastal town just south of Jacksonville with shopping, beaches, and an awesome downtown full of cobblestone streets, ghost tours, and little eateries. Lake Wales is a lake town full of families that have been there for many generations, which means fantastic stories and homes, and a feel of down-home magic.
I'd rent a beach house or a house near historic downtown. Downtown is full of cute shops - think art, stationary and other gift items, locally made soaps and the like - and some really great restaurants. There are a couple of pizza places we especially like. We like Pizzalley's for a more leisurely table service experience. Sit on the deck and sip a Blue Moon! It's Pizza Time will fill your need for a classic piece of Brooklyn style pizza. The place is narrow and crowded so you'll even feel like you're in New York! We took our box of pizza out to the water and sat on a wall at the beach's edge. Spend your days on the beach, or take a day or two to explore Jacksonville. I always hit up the St. John's Town Center for some shopping (bcbg, lululemon, J.Crew, West Elm). It's a gorgeous outdoor shopping center and I always find some great deals.
You must stay at the Chalet Suzanne. This place must be on a list of the country's top unique historic inns. Think Wonderland, reimagined as a hotel, surrounded by orange groves. Each room is completely different from the layout to the charm. My room had to be the best there is: It had a foyer in the center, a sitting parlour to the left with a collection of cool chairs and a view of the lake, and then the bedroom (king sized thank you very much) and bathroom to the right. Even the water pressure was fantastic. Throughout the day, small planes come and go as people come in just to have breakfast or lunch at the restaurant. And I had the breakfast: perhaps the most phenomenal pancakes I've ever had. There's a pool on the property, but definitely spend some time on the nearby lakes as well. Other things to do? Take an air boat tour to look for gators (what I've dubbed gator peeping) for an authentic Florida experience. I saw 3-4 of them ranging from small to really-scary-big! Visit where they make Florida's Natural Orange Juice (it smells divine!) and definitely have dinner at the Crazy Fish Bar & Grill.