If you plan to stay in Key West for more than a just a couple of days you might want to consider a day trip driving through the Lower Keys which would considerably enhance your Florida Keys experience. A navigation system is not really needed for this outing but is recommended because the graphics constantly show just how narrow most of the keys actually are and many visitors are surprised to see just how close to the water, either the Atlantic Ocean or the Gulf of Mexico, they actually are during their entire drive. I recommend driving as far as Marathon, which is typically considered the halfway point of the keys. An interesting way-point before reaching Marathon is Big Pine Key which is the only place that you will see Key Deer. These are a beautiful smaller scale version of deer that most of you are accustom to seeing and they can be seen along the roads that crisscross the island and some actually appear to be posing for photographs. It is illegal to feed these deer however it is obvious that they are illegally fed from cars in the roadway and many are killed by auto traffic. So please do not feed them as it encourages them to wander on or close to the roads.
A good spot to stop in Marathon for refreshments and a fantastic view of the ocean and the Seven Mile Bridge is the Sunset Grille and Raw Bar located on the south side of US 1 immediately after crossing over the bridge. This open-air bar is usually blessed with a cool breeze which makes the adult refreshments taste even better.
If you only plan on being in Key West for couple of days I would forego the car excursion and stay in Key West. There are plenty of things to do on the island to keep you happily occupied. Every arriving tourist is aware that a long standing tradition is to watch the sunset at Mallory Square. Sunsets can be beautiful and they usually are but the Mallory Square experience can be mostly about capitalism. There are hawkers trying to sell you everything under the sun in addition to the numerous entertainers who are also vying for your money. Some of these entertainers are quite good while some should be embarrassed to be there. Despite these insignificant drawbacks, everyone should view the sunset from Mallory Square at least once. However; there are other locations on the island that provide equal or even better sunset viewing opportunities including the “The Top” rooftop bar at the Crowne Plaza La Concha Hotel on Duval St. The Top also provides an unrivaled panoramic view of the entire island and there is no one trying to take your money except the bartender.
There are a number of places that you should visit and things that you should do if your time and money will allow for it. A relatively short and easy walk will allow for a relaxing and educational visit to the Harry S. Truman Little White House, The Ernest Hemingway Home and Museum, The Audubon House and Tropical Gardens, and the Key West Lighthouse & Keeper’s Quarters Museum which can be completed in a single day with plenty of time left over. All of these attractions charge an entrance fee but in my opinion they are all worth the money.