The Old Town part of Key West is the original part that was first settled. It is also the most desirable land, since it is the highest. Even during Hurricane Wilma which flooded most of the rest of Key West, the Old Town area was not affected.
The homes in this area are so beautiful. They were built in the 1800's by wreckers, cigar makers and tropical tycoons. Often the wood that was used to build the houses, came from the ships people used to get here. The conch houses are lovely, the style is a bit like New England architecture, but they have larger porches and smaller dimensions. All the houses in the Old Town area are very well kept up and maintained. They look beautiful and we had a lot of fun just strolling around and admiring them. Make sure you stroll leisurely and explore the many little side streets. Here you will find banyan trees, tall palm trees and unruly exotic flowers threaten to overtake the little wooden houses.
Look out for the "gingerbread" on the houses - this is the carved woodwork which is individual to each house. Amongst some of the gingerbread we saw were shamrocks and gingerbread men.
The Conch Tour is a sightseeing train that focusses on the Old Town area. It is an excellent way to get your bearings and to hear more about all the architecture, shops, historic buildings and natural wonders. I would advise doing the tour in the morning. The little train is open sided and the sun will be beating down on you later in the day.
The highlights are the seaport, Duval Street and the Hemingway House. Our tour guide was excellent - informative and very interesting.
You get tickets at the depot which is near the corner of Duval and Front Street. It costs $15 for adults and $7 for children. The entire tour lasts about 90 minutes. There are 3 stops on the way, but the train has a break back at the station after 45 minutes. You have 10 minutes to get out and stretch your legs. We bought key lime pie on a stick from the shop by the stop - it is the most delicious thing ever. You can take ice-creams, drinks etc. back on the train.
Duval Street is a mile long and stretches from the Gulf of Mexico at one end to the Atlantic Ocean at the other. It has lots of bars, restaurants, t-shirt shops and tour company offices. Apparently it was just on the safe side of seedy for many years, but now is a well tended strip of shops and is a really pleasant place for a leisurely stroll.
Fast Buck Freddies is an interesting shop on Duval with toys and trinkets. Children love it - it is a bit like a mini tropical department store and the window displays are fun.
As you stroll, definitely try Key Lime Pie dipped in chocolate - it is heavenly. Also we loved the (huge) warm cookies from Cafe de Paris. You will chuckle at the many silly t-shirts displayed in the windows of the tacky tourist shops. Don't let your children look at them too closely though - some are very risque and require a bit of explanation!
Look at the city hall building on Duval, apparently it is an exact replica of the one in Havanna.
Duval Street is absolutely buzzing after dark, with live music in all the bars. The atmosphere in the evenings is fantastic.