Best Time to Go
According to one local, November is the best month in Key West. The crowd is minimal and the weather is perfect. High season in the Keys is mid-December through March, and traffic on the Overseas Highway (and seven-mile bridge) is terribly heavy. From November to the middle of December, crowds begin to wane, and the weather is out of this world. However, summer, even though hot and humid, is becoming a second high season, especially among families and Europeans.
During the summer, the average high reaches the upper 80s to low 90s. During the summer months, you can also expect more rain in Key West, mostly in the form of thunderstorms. Usually the storms pass rather quickly, although driving in them is not recommended. During the winter, Key West boasts a pleasant climate, with temperatures averaging 75 degrees. The humidity is no where near the summer levels and the water is perfect for swimming.
The recommended mode of transport around Key West is by scooter or bike. Walking is even suggested over the use of your car. Parking is scarce in Key West and you'll pay a pretty penny to do it. If you're flying in and strictly plan to stay in Key West, you don't even need to rent a car. However, if you're planning to peruse the other Keys, you'll definitely need a car.
Avoid Key West in March, when spring breakers line Duval Street. Hotels, motels and inns significantly drop rates during the summer months – by nearly half the going rate. The high season is winter and costs are known to nearly triple.
If you've got a few days to spare, head to Miami. Roughly four hours north of Key West, Miami is home to the famous South Beach - a hotspot for nightlife.
Key West isn't the only Key. There are several more. Take a drive up US Highway 1 and you'll pass Duck Key, Cow Key, Big Pine Key, Islamorada and Key Largo.