We make the trek from Chicago every December/January. The weather is usually great in December but can get a little cooler at times in January. No humidity and the nights are great for walks for bike rides, we we do daily!
Crowds are virtually non-existent in December, so the usual laid back vibe is even more so.
The restaurants and bars are almost all great. I'd stay away from the north end of Duval, where all the cruise ships come in. Quite a few places are over priced and occasionally not so good. I use the Urban Spoon app on my iPhone to check ratings; they usually dead-on.
Check out http://www.keywesting.com for good information about this little slice of paradise.
Fondest memory: Always a good time at Capt. Tony's Saloon!
Favorite thing: Check out the Green Parrot Bar. It is one block away from Duval on Whitehead Street. Great music and much more of a local flavor since the tourists do not flock by there. For Fantasy Fest they host the main body painting contest.
If you are looking for the "main" road in Key West, you are likely seeking Duval Street. Here, you will find all of the shopping and eateries that you could desire. Within walking distance of this street is also some of the major attractions of the island such as the Hemingway House. You will see a lot of trendy places here. If you like art galleries, you will likely find some type of exhibition here. The architecture is definitely that of South Florida and you should see some of the art deco style and bright colors similar to Miami Beach.
Fondest memory: Strolling down the street in shorts and a T-shirt with pleasant weather while the rest of the country was beneath an arctic air mass.
I was on the Duval street to meet 2003 with 1000s people around. Everybody was screeming, drinking beer, dancing and laughing. A man throwed us beads from a roof. It was fantastic experiance for me to be there at that moment, because I am from East Europe and it was my first trip to USA. Unfortunately I forgot my camera at home :(
(I know, shame on me.)
Fondest memory: It was hot weather even in the midnight, but maybe it was because of champagne and beer - hahaha.
Most things are within walking if not bicycle distance. Live and let live attitude of local residents. Plenty of tourists looking for a good time. For some reason, people get here, and they want to let their hair down, so to speak. They will do things they would never do in their own city.
Fondest memory: Looking over the sunset, beyond it, and thinking how close I was to Cuba. The ocean smells. The fresh fish. The cold beer. This is the only place I don't care what brand of beer I drink. As long as it is cold, it's refreshing, and it tastes good to me.
Sample the excellent restaraunts. Rent a moped and cruise the island - a couple hours should do. Visit Ft Zachary Park - a nice public beach (small entrance fee), though a bit rocky. Excellent shade trees to enjoy the breezes and watch the ocean.
Fondest memory: Walking the streets and enjoying the people and the craziness. Pictured is a sample costume from the Fantasy Fest parade.
I have been to Key West many many times, however, the times I had the most fun is during Fantasy Fest in October. Key West just becomes completely wiiiiild and the gay parade is fantastic!
I promise I'll add a picture soon....
Fondest memory: This isn't my favourite memory but the thought of it still makes me laugh. We were walking down Duvall St when a very chatty drag queen stopped us. Just wanted to talk and talk, 'Where y'all from'...'Toronto,'...'Toronto? I just love Toronto!' and so on. I should have asked how he/she managed to walk in the 4 inch heels he had on! Was probably 6'4' in them.
Favorite thing: Reminiscent of main street USA, Duval Street is the hub of most Key West tourist activity and nightlife.