Key West, the southernmost city in the continental US, is closer to Cuba than it is to Miami. Just a couple of blocks from the party street named Duval, you’ll find yourself in the Truman Annex, which has both historical significance and the most charming examples of Americana one could hope to find.
You’re also a short stroll from the entrance to a naval air base, an in-town lighthouse, and sites such as Ernest Hemingway’s Florida home. The city has an interesting healthy rooster population as well; more on them in an upcoming post.
Come evening, there are a number of spots from which you can enjoy a great sunset; I caught this one from Mallory Square.