The Acropolis
Photo: The Acropolis / iStock.com / Lefteris Papaulakis

6. Pick a theme

A general tour is going to be just that — general. If you’re after a more in-depth experience, find a tour (either organized or self-guided) that concentrates on ancient Roman or Greek sites, or Baroque and Renaissance architecture. Mediterranean cities have deep, deep history, and hiring an expert can uncover many of the secrets behind the landmarks. Archaeologist Dr. Paolo Gardelli leads expert tours on day trips to Pompeii. Or contact the art history, architecture, and science experts at Context Travel; the company arranges guided walks with experts in all major Italian cities as well as Athens, where you can book a private architecture tour of either the city's modern buildings or ancient sites like the Acropolis.