Love Anacortes also. We stayed at the motel at the ferry landing there. Beautiful area and I envy all of the folks who call it home (in the Summer).
When you get to Key West there is a taxi company that has an all pink fleet; I don't recall the name but there is a numeral included in it. Find out which company it is and ask if it is possible for Joe Cotton to be your driver. Joe could pass for a pirate from days gone by, has lived In Key West for 30 or so years and knows the area like the back of his hand. If you can get in his cab just tell him your a friend of a friend of his sister Barb.
When you get homesick for the water, and how can you help not while in the Keys, find Captain Jim Peabody for a charter (bring your checkbook); see if you can team up with someone else to defray the cost. If you contact him tell him Vince with the Boston Whaler he took to Bullfrog Shoals says hello.
Some fellow guests at Parmers Resort on Little Torch Key rented a sponsoned boat/catamaran (not really sure what to call it) in the area for 5 days for $900 or so dollars. I remember him saying that he'd negotiated the price down from $1,100 or so dollars. As with most anything, price depends on how much business they have when you want the boat. The boats were very low hour 20'+- and have 90 HP Mercurys on them. I wish I could remember who he rented them from. Try asking the floks at Dolphin Marina (first left after crossing Big Pine Channel onto Little Torch Key) if they know who it might be. All of us familiar with the cost of ownership of boats appreciate that this is not an unreasonable rental fee on such a craft. There are also glass bottom boat trips as well as head-boats available in the area.
An excellent place to eat is the Square Grouper on Summerland Key.
My knowledge of the Keys is limited to one week in the area of Little Torch Key this past Christmas. I'm sure others have more information they'll gladly share.
We found that the local folks are genuinely friendly and willing to help you enjoy your visit to the Keys. Have a great time and let us know how the trip goes.
CV