A trip to Key West was high on my list of where I wanted to go + things I wanted to do while I still could. Because I was in a motorized wheelchair
my attendant and I had to pay $800 pp to fly from Orlando, Fl. to Key West
( about 50 min. flying time) more than 2X the cost to fly from New England to Orlando because they had to transport the wheelchair.
Prior to going to Key West I contacted the appropriate offices to inquire about wheelchair accessible transportation since I am in an electric wheelchair and was told there was an Island shuttle than was accessible
and public buses that were accessible so there would be no problem. From the time I arrived on the Island transportation was a constant problem. The shuttle driver drove in such a manner that I was bounced up and down the entire trip. I had such pain from the travel I had to keep paying for massages at the hotel to relieve some of the pain. One driver drove right past me at the stop and there wasn't another one for 2 hrs.
The 1 life dream I had left that I would be able to do was Parasailing. My appt. was made well ahead of time. The am of my parasailing I heard a weather forecast ( at 5 am ) of winds picking up around noon. As soon as the business opened my attendant called and informed them of the forecast and asked if we should come sooner so as not to risk missing the parasailing.
A representative of the company responded with oh no we always go, no problem show up for the 1pm appt. I got there at 11:30 am. checked in and was told to return at 12:55pm. When I did they told me they would not take me up because it had gotten too windy.
I could go on but I'll spare you all the other woes. After spending thousands of dollars all I got were apologies from the hotel which didn't have the correct type of room reserved ( handicap accessible ) and heartache for an activity I'll never get to do I would strongly recommend that people in electric wheelchairs think long and hard before going to Key West. They will promise you whatever you want to hear but once you're there you are lost.

Have visited Key West w/ my spouse 3 times and have tried several different restaurants and bars there and thought I might share a few opinions for what it's worth.

Favorite Restaurants:
Turtle Kraals -- the food is not "blow your socks off" great, but it is good, fairly priced and the service is friendly and efficient. We love sitting in the open air restaurant and watching the boats come-n-go from the wharf.

A&B Lobster House - food is a tad better than Turtle Kraals but it is also a tad more expensive. Service has always been excellent. We love sitting outside and enjoying a cool drink here. Fantastic conch ceviche.

Bahama Mamas - a little hard to find but the food here is the best we have had on the island. Not expensive and service is friendly but can be a little slow, but I think that is mostly because all the food is made by hand (no reheating frozen conch fritters or anything like that). The curried conch is to die for.

Favorite Bars:
Captain Tonys - this is our favorite bar and the first place we hit as soon as we arrive in Key West. We end up here every night it seems. We love to sit close to the street and people watch. Service is friendly and the bands are usually quite good. Most of the cruise ship people go to Sloppy Joe's so you get less "tourists" and more "visitors."

Green Parrot - local bar. It is usually pretty steamy in here (it's hot and humid and there isn't much air circulation) but the atmosphere is rough & low key. Good people watching.

Other Tips:
Sloppy Joe's is utterly over-rated. By 10am it is jam packed full of "cruise ship people." It stays that way all day until the boats leave and then it is full of drunk frat-type people. Hemingway also drank at Captain Tony's (which was the original Sloppy Joes) so I suggest heading there instead if you're doing the "I drank where Hemingway drank" thing.

Fort Zachary Taylor & beach - best beach on the island but that isn't saying much. The fort is mildly interesting and they do a nice tour every 30 minutes or so.

If you have the time take the day trip to the Dry Tortugas. Beautiful islands, interesting fort and great beaches. It's worth the time & money. The boat ride is fun and you'll usually see dolphins & sea turtles.

Several people have commented that servers in KW are rude and hate the cruise ship people and this is overall true. Sometimes 2 or 3 giant ships will dock in a day and the island is flooded with people and their kids. We have witnessed some of the rudest people come off these boats - they act as if they own the island for the day and yes, they are terrible tippers. So, it shouldn't be much of a surprise if the locals are not welcoming you with open arms when you have on your Carnival cruise t-shirt. In general, we have noticed that the locals treat you differently if you are staying on the island...they seem to think it's more respectful. At any rate, treating the locals w/ respect and not as your beer wench will go a long way. Most of them have interesting stories to tell if you try to get to know them. When we have heard a server make a comment about hating tourists we usually strike up a conversation with them about why they feel that way...next thing you know you're getting all the good scoop about people, good local restaurants and bars, etc... Without fail, what has on occasion started out as a "rude" server ended up being one of the nicest after sitting at the bar and talking to them for 5-10 minutes.

Have fun and relax and you'll have a great time!

My family spent a week in Key West (June 20-27) and had a great time. Here are our recommendations. First we stayed at Southernmost On The Beach. See my review under the hotels of Key West. One of the first things you need to give thought to when traveling to Key West is how you will get around the island. The distance from the south end to Mallory Square is about 1 1/4 miles. We walked! There are bikes, scooters, small electic cars, etc., that you can rent, but they are EXPENSIVE! This could be a deciding factor on where you want to stay. We walked down Duvall Street just about everyday, we got tired, but it was not too bad. We did decide to use the "Bone Island Shuttle Bus" on one day. This shuttle bus service advertises to take you around Key West all day for $7.00 per person. I now call this the "Bonehead Shuttle". We waited FOR EVER for a bus to pick us up at several stops. Finally we decided just to walk. I would not recommend this service. Ok places to eat. We ate at Crabby Dicks, Duvall Beach Club, Sands Beach Club, Half Shell Raw Bar, and Alonzo's. Of all of these places, Alonzo's was the best. If you like seafood, Key West has some of the freshest and best. Attactions to see. We went to the Aquarium, Lighthouse, Earnest Hemmingway's home, Fort Zachory Taylor & beach, Mallory Square, and of course Duvall Street. Attractions in Key West are EXPENSIVE, so if you are on a budget, you will need to select the one's you really want and pass on the one's that are maybe's. You will want to be on Mallory Square for the sunset celebration at least one night. The square performers and vendors are very interesting and the sunset is great.

Beaches. If you are going to Key West for the beaches you maybe disappointed. There are very few beach areas and they are somewhat small. We stayed near South Beach and it is very small. Fort Zachory Taylor has a beach (cost $3.50) but it has small pebbles and are tough on the feet. We did not go to Smathers Beach, but this may have been the one to go to. In any case if you are a snorkler, then these areas would be good. If you are a swimmer, there is A LOT of seaweed in the water and it smells. If you are just a sunbather, then it may not matter.

Overall, we are ready to go back to Key West. A lot of sun, water, seafood, and relaxation. My kind of vacation. We were a little concerned before going to Key West that it was not a "family" type of place. However I must say that it was not a concern, but we were back at the hotel at 10:00pm. I expect if you stay on Duvall Street late at night, this might change. Also there were nude bathers at one of the piers. Other than this, no issue.

I would recommend a Key West vacation to anyone. In the words of my deceased grandmother "When you go to Florida, (in this case Key West) take Few Clothes and Plenty of Money".

The Florida Keys are breathtakingly beautiful! I loved the sunshine and the sunsets were just as they promised-just wonderful! I recommend getting
to a calm spot as quickly as possible when you see the sun getting close to the water. I tried too many times to watch it from the car. The best way was when I took one of the sailboat cruises from Key West. You can find a Sunset cruise for about $30. There are all kinds of coupons and information at the information center at Mile Marker 1 or 0. Everything goes by Mile Markers in the Keys. There is one major highway-Highway One. It ends in Key West at MM0. You will see this all over Key West.
Key West architechture is beautiful. Tropical. Ernest Hemingways home is there to see. The city has many buildings yet does not feel crowded until you go downtown to Duval St. Southernmost tip is near end of this street or maybe even on it, PARENTS TAKE NOTE about halfway down Duval to the end almost you will see all kinds of everything!
I would not bring my kids to that section. It is rated X. There is nudity, profanity on t-shirts displayed in windows and doorways and on the streets, transvestites, female impersonators, etc.
Now I am not judging. I am not a prude. I mainly say this as a warning to parents because I am a parent myself. Simply said, I just would not bring my kids to downtown Duval St Key West.
The Key West Butterfly & Nature Conservancy is an interesting place. It is on Duval St.
The local seafood is great. I tried things I never had before and I was not disappointed.
You may notice some hostility in some people towards tourists. Not too long before I came three cruise ships came and unloaded all their people-at the same time-into this small area! It was just overwhelming. So we just have to remember that the locals are only human too. But it's not easy. You want to feel welcomed in a strange place.
Another great thing I tried was the fresh fruit drinks that were sold along the street. My favorite was the Strawberry-Mango-Coconut. Mmm.
There are many things to do and see in Key West, but I think one of my favorite was just to BE in Key
West. The weather is so perfect. My body was not bothered by any allergies except for one episode at the beach and I don't know why. It may have been the sunscreen I used. Otherwise I have never felt better. The breezes and the air were so easy to take and the nights were not cold. I kept waiting for it to get cold or for the clouds to come in and block out the sun like I'm used to in NY and it just did not happen! It rained my first couple days there, but it did not rain all day like it does here. And the clouds don't come in and stay for a week like here in NY. It was just great. I liked it so much in the Keys I decided to move there!
Yes I took the plunge-only I did not move to Key West. It was a nice place to visit, but too expensive to live there and too hectic and crowded for me. I moved up to the middle Keys to a quiet, calm spot where I hope to live in peace!
I hope this helps your vacation in paradise. It really can be paradise if you make the right choices.