Every downtown should have a place like this. We always have so many questions and residents are very helpful in Key West. The big questions we like to just bike over to Greene Street and ask them. These folks know how to guide us tourists and put things in very simple terms. Most of the things you will likely ask about, they will have a brochure to give you for guidance.
We've come down a bunch of times from Miami and considered the Florida Keys our second little vacation home. A couple of conclusions have been developed. Everything is about the weather, so you want to plan your water-based activities around the best days in the forecast. And you really need to understand the wind direction, as one side or the other of the island is typically nice and smooth.
Bicycles are the key to Trips on the Island. Bring them to save money, just keep them looked up when in the bars. Also, the Galleon is a secret, but the best Thing to Do is at Sunset.