Once landing at the Key West airport in that tiny connecting airplane, you will be ready to celebrate LIFE!! Key West has plenty of places to go and do that! Duval is the place to be. There is a great variety of bars, restaurants, and shopping along this street. My favorite restaurant was Mangoes, my favorite clothing store was Fresh Produce, and my favorite bar was Captain Tony's.
For nightlife, you can listen to live music, dance, sing karaoke, or watch a drag queen show! Stop by the famous Sloppy Joe's and Margaritaville for some neat souvenirs in the gift shops! Mallory Square shouldn't be missed for the sunset celebration, especially if you're a people-watcher. There are a lot of sidewalk entertainers there doing anything, from acrobatics to fire-eating. You can also find artwork for sale in an art-fair atmosphere and more souvenirs at little tables around the square. This is where the cruise ships dock. If you're not getting off one, they're fun to check out, too.
Duvall is also a mecca for shoppers. You can find great clothes, fine or costume jewelry, and shoes made right in Key West!
We had a lot of fun cruising with Danger Tours. We did a snorkel/kayaking trip with them. The captain and first mate were welcoming and hilarious! It was windy while we were there, so we couldn't go to the coral reef, but rather to the sponge garden. It wasn't the greatest, but it was still fun for my first time. While kayaking, we saw a shark (okay, so it was 1 foot long!) and stopped at a small beach.
Tour the city on the Conch Tour Train. You can see a lot in a short amount of time and get the history of the island and special places on it.
Quick Tips:
This really isn't a place to bring children. Save this one for an anniversary trip and leave the kids at home. Key West is great fun for grown-ups, but also very commercialized. If you want to have a quiet, laid-back vacation, you may want to stay close to your resort. If you want to party and be a part of the action, try to stay somewhere near Duval and Mallory Square. That's where all the activity is.
Best Way To Get Around:
Rent a scooter, as they're a lot of fun and easier to find parking for than a car. There is very little available for parking on Key West, so I'd forget about renting a car. You can find rental places at the airport, but you can also take a cab to your hotel (with your luggage) and find scooter rentals just off of Duval.