The Rooftop Café
308 Front Street
A beautiful and romantic setting, with trees growing up through the deck and a nice big bar serving luscious libations.
The Rooftop is a great place for lunch or dinner and also fits the bill when you're looking for a place to sip a well-mixed cocktail or glass of wine.
The food has been up and down over the past few years, so I don't recommend it as highly as I once did. Still it is such a pretty spot and in Key West, things change so quickly, you could find it perfect!