The Italians came to Key West based on the fact that the island has a rustic feel and fun vibe that blends together well with the practicalities of Italians and Italian-Americans.  Although its a small place the food choices are covered depending on the type of Italian cuisine you're craving.  If you're seeking northern Italian we recommend Antonia's by Antonia Berto.  The pasta is made fresh, the carpaccio is tinged with truffle oil and the wine list includes specialties such as: Cum Laude Castella Villa Banfi 11, Amarone Della Valpolicella Forno Romano 08 and Soave Classico. If you're seeking a family friendly Southern Italian Cuisine restaurant you might consider Abbondanza.  Since you are in the keys you may opt for Italian with a seafood slant.  Our recommendation is Salute by the Beach.  Try the tropical scallops and of course key lime pie!!  Mangia va Bene Key West!!!