Insiders Guide: Key West
The best way to describe the “honey hole” that is Old Town, Key West, Florida is to take the number of significant 19th and early 20th century houses found in a typical location such as a small town or geographical region, multiply that number almost to infinity, pack them all together inside a square mile, give or take, and then dress them with giant palms, banyans, kapoks, poincianas, live oaks, and the entire botanical index of every other tropical tree, plant, or shrub that comes to mind.
Your end result, within that square mile (give or take), which is bordered on one side by the Atlantic Ocean and on the other by the Gulf of Mexico, is a collection of more than 4000 historic structures. Those zeroes beside that 4 are not typographical errors.
Small wonder, then, that I will struggle to present an Insider’s Guide to this charmed island that even scratches the surface. Most visitors here are on the island for a compressed and hectic cruise ship day, or a weekend, or a week, and within that time frame, absorbing every single architectural gem is not possible. For frame of reference, I have been visiting for 20 years on a regular basis, and I have yet to see them all myself.
That’s the bad news.
The good news is that it’s possible, even within a cruise ship schedule, to rent a bicycle, a scooter, or a golf cart, hit a significant few streets, and come away having seen and photographed enough historic houses to keep you satisfied for a long time.
So let’s talk about those significant streets.