We love Key West, we go once a year after the winter season is over. We have driven and taken the Ferry, but now we prefer to fly South West out of Orlando and have a cab take us to our hotel of choice. We stay right on Duval Street at La Concha, which is considered a historic hotel on Key West. It is decorated in the old period style. Hemingway and all his buddies used the hotel as their "watering hole" and there are photos of him everywhere.
If you go make sure to get to Mallory Square every night for the sunset and free entertainment, and also to watch the chickens roost in the trees on the square. Also, for us, it is a must to eat at La Trattoria, a superb Italian restaurant right on Duval.
We don't bother with a car, you can rent a golf cart, use the Conch train which runs out of Mallary Square, and there are also bicycle cabs like rickshaws which are fun.
We miss a real night life and Duval street comes "alive" at night. We stay for about three days and get our night life fix.
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