We took the 4-hour drive from Weston to Key West. We stopped at the Florida City Outlet on the way, but it was a waste of time, as half the mall is closed. The drive down was slow but beautiful. All the bridges and water are clean and in good shape. There are lots of police on the way, so don't speed.
Once in Key West, we were surprised at the amount of damage from the hurricanes in the early summer still at the end of the summer. The downtown was still busy at night. There are a lot of sights to see in Key West, and there are coupons in all the travel info spots on the way. You can rent a scooter to get around town. Parking costs everywhere. There are many nice local places to eat. Duval Street is the main street to walk around; you can walk from one end to another in less than an hour. Most of the shops are very expensive, so it's more about window-shopping than take-home shopping, but there are a few tourist shops as well.