Under $100: Palermo

For breakfast, have a café and a brioche ($5) in one of the many cafes on the Via Bara All’Olivella, one of Palermo, Italy’s main market streets.

During the morning, book Don Saro’s free walking tour of the city. Don Saro is enthusiastic and knowledgeable and will customize your tour to you for $5–15 based on what you feel comfortable tipping.

Trattoria Familiare da Michele & Jolanda is a true family-style Italian restaurant and opens early for lunch. You are sure to become family before you leave. Be sure to try the cannoli; after all, Palermo is the home of cannoli and this restaurant may just serve the finest in the city.

Relax in the Mediterranean sunshine at Mondello Beach, a short bus ride ($3 round-trip) from the city center, during the afternoon. Grab an arancini from a street vendor or at a local café ($6). Or if you’re feeling like something more than a large rice ball, back in the city stop by Bar Touring for a selection of cheap Sicilian treats. And do not leave the city without having some gelato!

Next take in a show at the Teatro Massimo, the largest opera house in Italy and third largest in Europe, ($10–30 for the cheap seats). Though not as famous as La Scala in Milan, the Teatro Massimo features exquisite decoration and is famous for having perfect acoustics.

Finally, head over to Vucciria and Garraffello (free!) for Palermo’s all-night, bohemian street party. Drink and dance in the courtyard under the facades of ruined buildings that haven’t been repaired since they were bombed out during the Second World War. Or, alternatively, check out a concert at the Palab Cultural Association.

End the night with a greasy Pane con la milza ($5) from a street vendor. Nothing says, “I just had a killer day,” like a spleen sandwich.