1.Definitely go to Blue Heaven, Key West’s most famous restaurant, and definitely go for breakfast. Have a cocktail at the bar (yes, at breakfast, you're on vacation!), eat in the open air under the tree canopy, wild chickens scratching, live music. Heaven indeed. What to order: their lobster benny, without a shadow of a doubt.
2.Fly by seaplane to the Dry Tortugas (tropical islands). You'll do all of the following in half a day: sea plane, amazing flight, tropical island, snorkelling....There are so many reasons why this is an amazing once-in-a-lifetime trip. You get to land on the water. During the flight the altitude is only 500 feet, so low you can see the sea life swimming below in the blue waters. When you get there you have the island to yourself (and the few other passengers of the sea plane) for an hour before the hordes arrive (the daily ferry) so you can snorkel in peace (this is the best snorkelling location in Key West). Take the half day trip and go in the morning. Book before you arrive in Key West as the trips sell out.
3.Drink the largest, strongest and best martini in Florida at Virgilio’s martini bar on Duval Street. All the martinis are great, the best is the raspberry chocolate bomb. A challenge: see if you can survive two of them! Other bonus: you get a great view of Duval Street madness from your barstool.
4.Wander the streets of Old town off Duval Street. Take your camera to capture the beautiful houses, flowers and trees.
5.Eat! - I’m going to put all my dinner recommendations in one, here they are: Michaels for the best steak and dessert (chocolate volcano). The tastiest fish in the world is Hog snapper and it’s the speciality of fish specialist restaurant Cafe Sole - the best single fish dish in Key West. Finally, for the best lobster and the best dinner table view on the island go to the A&B Lobster House (the restaurant on the first floor). If it’s not too humid, get a table outside on the deck - views of the harbor. All three restaurants will get super busy so book in advance.
6.Go to see the hilarious drag show at Aqua on Duval. Nightly but pick a night Inga is performing.
7.Take a drink at legendary Sloppy Joe’s on Duval Street. In the 1930s it was Hemingway's regular bar. Take pictures of the iconic neon sign.
8.A fun way of seeing the whole island in comfort and all in just over 2 hours, with a very informative live commentary, take the bus tour or as they call it here in Key West the conch train tour.
9.Walk up and down Duval Street. I know you are going to do this anyway.
10.Chill on the beach. The best beach in Key West is Fort Zac - it’s beautiful, but not sandy (rocky bits/limestone and coral pebbles). If you really really really want sand go to Higgs Beach but it’s not as pretty.
11.Walk the boardwalk on Key West’s historic harbor. There is always a hundred things going on, great people watching and of course views of the ocean. Really worth the diversion from Duval Street.