Hello from beautiful Key West!!
Yes,I live here and only a couple of minutes from the dock (in Truman Annex). Just today DH & I heard the Disney horn. It's great to hear that!!! Once,many years ago,when we stopped in KW, I timed the deivery of patio furnture to arrive when we did. DH & I got off the ship,unpacked and put together the furniture and got back on the ship. We had the most boring shore story to tell at dinner out of the whole table.
I would STRONGLY recommend taking a Conch Train tour first thing off the ship. Walk through the Mallory Square shops to the front & you can pick up the tour right there. It'll take about an hour, but you'll get a great overview of Old Town and some of the history of the city, of which there is alot.
Trumans Little White House(where the President vacationed while in office),the Hemingway House,Lighthouse, are all within walking distance. If you really want to feel like you're in the caribbean,rent a bike,
scooter or electric car & tool over to Fort Zachaey Taylor State Park,which is also near the dock. You went past it on your way into KW. It was the beach with the pine trees. The Gulf & Atlantic meet there,so the water is always clean. It's also the beautiful blue/green color that caribbean water is known for. Bring water shoes, as there is alot of keystone(type of limestone) strewn about. Yopu'll see pelicans and there are tropical fish hanging out by the rocks,so snorkeling is nice there too.Also don't forget sunscreen-this climate is sub-tropical,so 15 minutes in the sun can cause some major sunburn. But there are picnic tables under the trees and umbrellas and chaises can be rented. There is also a concession stand that sells good sandwiches and frozen key lime pie on a stick. There is a civil war fort there also that's interesting to walk around. Eat lunch at Schooner Wharf (at the Bight,marina), at the end of Greene St,which starts at the corner where the Mel Fisher Museum is, in front of the Custom House,the big red building. You'll get a feeling for Old KW in the area of the Bight (pronounced BITE). Believe it or not,the cemetery is a huge tourist attraction. There is an area showing respect to Cuban Immigrants, who were prominent in KW history,as well as an area where some of the sailors are buried who died in the explosion of the USS Maine. There are interesting headstones,such as the woman who was always a tad overly concerned about her health-her headstone says "I Told You I Was Sick!"
If you have time to head to New Town,in front of the airport is the East Martello Museum which not only houses a great historical overview of KW(once the richest city in the country due to wrecking), but you'll get to meet Robert, the "enchanted" doll (sounds better than saying haunted). Just ask Roberts' permission to take his picture or you'll end up with an "exposure issue". Robert is sensitive...........
Walk all the way down Duval & you'll see terrific art galleries with items you won't see anywhere else. Both you and your son will truly enjoy the sculptures/paintings,etc. Take pictures, as you might not be able to describe some of the art,it's that different (who knew frogs could be so funny!)! I guarantee you won't see Rupert the Ostrich anywhere else, either(he has his own gallery).
Definitely go to Mallory Square for Sunset. The performers and local artists are now"juried", having to meet certain standards,so the "shows" are interesting and craftspeople talented. Not like back in the day when it was all about whoever showed up & did whatever they pleased-it's much more civilized now so it will appeal to a broader range of tourists-it lost some of the original character,but the sunsets are still as beautiful as ever. Grab dinner at the top deck of the Westin about an hour before sunset, to grab a good seat.
Depending on how long you'll be docked,you can actually get in alot!!
Try the Key Lime Pie from each company/person who sells it. Everyone has a different recipe and it's interesting to experience how the taste varies.
Have a wonderful time!!!!!