The Ernest Hemingway Home and Museum (home of many six-toed cats!), the Southernmost point buoy and, briefly, Fort Zachary Taylor State Park. Briefly because when we arrived some epic torrential rain decided to join us. Doh!
Sloppy Joe's, a rather famous bar on Duval Street. The ambience is definitely touristy and not what it would have been like in Hemingway's day, but pop in for a drink to say you've been. Another great place to head for a drink is Sunset Pier, right by Mallory Square. Funnily enough, it's the perfect spot to have a cocktail (rum runners FTW) and enjoy the sunset! We enjoyed a local speciality here, too - conch fritters - though Key West is known for its Key lime pie. Make sure you try a piece. Or two! And some Key lime ice cream from Flamingo Crossing if you need to cool down. (Maybe avoid the Key lime Cuban cigars though!)
The Flaming Buoy Grill Co. Definitly the best food we ate in Florida - the flavours were beautiful, plus the service was brilliant. For lunch, you want Bien (ranked #1 on TripAdvisor). I gorged on their awesome Carribean roast Cuban sandwich as Key West's famous chickens pecked at our feet. The taste! Those onions! Incredible. (And I'm not a sandwich person.) Other places we enjoyed: Onlywood Pizzeria Trattoria, Firefly (beautiful pulled pork), Bagatelle (the bread is DIVINE!), Charlie Macs and Sandy's (another great spot for a Cuban sandwich). One thing to note though if you're there off-season is that some of the bars and restaurants are closed whilst the owners are on *their* hols.