In January, you run the risk of real cool weather. In February, your cool weather risk is 50/50. So wait until March. Even better, wait until after Easter, when the college spring break crowd and snowbirds have split. The town will be much calmer, and you will be able to get reservations at one of my small handful of approved Key West restaurants. May and June are beautiful but getting hot, which is fine by me. In July, you had better be a hot-weather person for certain. If you’re not, I’d cross out July and August, and certainly the deadly hot September hurricane-risk season. October is fine, but you may be in the camp that is not quite up for Key West Fantasy Fest. November and December are fine choices, but— no surprise— you will want to reserve early. Have a great time, and don’t miss out on a visit to the Truman winter White House. It’s a nice, nostalgic tour. Next week, I’ll post you on how to get to Key West with some degree of comfort. It is quite easy to make a hash of the trip.
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Richard C. Young is the editor of Young's World Money Forecast, and a contributing editor to both Richardcyoung.com and Youngresearch.com.