Hemminway House, Truman Florida White House complex, and Mel Fisher Museum are my favorites. Just walking the residential streets for the architectural interest is also fascinating. The cemetary has the S.S. Maine casualties which bears recognition.
We were in Key West the second week of August and had a very quick visit...3:00 - 11:00 CST... (Royal Caribbean Rhapsody) which means it was 4:00 their time when we arrived.
So, we rode the Trolley to get a quick over view of the town. We had a good driver who
was most informative and answered all of our questions. There are several historic places we would have loved to have toured, but they were closed by the time we finished the trolley tour. We walked around Duvall Street to get some t-shirts for the kids and then walked to a neat restaurant on the water called the Conch Republic to have a snack...were anxious to taste several different "conch" recipes. We saw a lot of places on the tour we wanted to return to for better pictures, but the sun was quickly disappearing by now.
So, realize that your time will be short if you are in port no longer than we were and just enjoy a few things you are interested in. Research Key West on the internet and the info is abundant.
Depends on how long you will be there. We were only there for a few hours. Took the Conch Train around town and they pointed out all the interesting places, so you can decide where you would like to go back to if you have time. Saw most of the area that way. Don't book with the ship. Just buy tickets once you get there...it's cheaper and the tour is longer than the ship's tour.
The Conch train tour is a must, and the sunset at the southern most point is a great "high". Other than the musty museums there is not much else. This is a party town and if you are not there at night forget it !! Try out the Conch fritters at any of the open restruants. Duval St is just a trap, with expensive t's go to the side streets and get better deals. Been there done that many times. Love the keys for diving and great food, but to commercial for me.
A Florida native, Sea Trekker
Make sure to have your picture taken at the southernmost point and at Mallory Square at sunset. Mallory Square is near the port and late in the afternoon, it comes alive. It is very much a circus type atmosphere where you can see cats walking on tight ropes, people selling their wares and even a guy on a 10 foot high unicycle (my favorite).
If you don't do the Conch train or some similar tour of downtown, you can always shop on Duvall. There are neat shops down there, not just t-shirt joints. Also, there is a Hard Rock Cafe and a Margaritaville. There is also a pretty unique place I think on Duvall (all the way down by the Southernmost point) that has chickens walking through the store. Probably something you don't see everyday.
You can always rent a bike or have someone bike you around in a "taxi".
There maybe some pretty good bands playing in the local joints too.
Personally, I love Key West, even when there's no drinking involved. The beaches are pretty yukky, but there are other things to do. Last time I was there (in December 2003), we went parasailing (we booked through RCCL) and had a great time.
We'll be in Key West next Tuesday with the Rhapsody of the Seas. I can't wait, our trip for Labor Day was cancelled thanks to hurricane Frances!
The Conch Train is a great way to tour the key and see all the big sites. Other than that, theres not much to do except eat, drink and shop. There are so many great eats there-we like to hang out at Sloppy Joes. Just down the street from there towards the wharf there a great Key Lime store (owner is Kermit) that sells a ton of products made from Key Limes (their pie is good too). Right next door is one of my favorite jewelry stores Whitfield Jack. He makes all his own stuff and its pretty unique to the Keys. For great gifts other than tee shirts check out Key West Aloe (sister company is Waikii Aloe). They have cosemetics, sunblock, pet products, hair and skin products and perfume all made with aloe and scents that remind me of the tropics. I love the hair and skin care line (mago, rasberry, key lime, vanilla, banana, coconut, etc) which they sell in small gift packs or large bottles. Be sure to go to the factory store on the same side street as Sloppy Joes and across from Divers Direct as the prices here are cheaper than in their boutique store one block over. Also, there are usually coupons in the tourist books you see along the sidewalks. Across the street from there is a building that has Key West handprinted clothing. They have some neat things in there. If youre into trains, theres the Flager museum (really small and hot) that is about the train / overseas highway to the Keys. The ship will probably be gone by sunset, but if not check out the sunset celebration at the pier. Its very different, though not quite as eccentric as it was before they redid the pier years ago.