Italy

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Italy Itineraries

Long Weekend

If you have only one weekend, pick your city and do it right: Rome, Venice, or Florence. You can fly directly into the first two or take a high speed train from either to Florence. Since you can’t “do” Rome in two days, choose the theme or historical period you want to explore and focus on that. In Florence, visit the Uffizi museum, the Duomo, and Michelangelo’s David, and “window shop” on the Ponte Vecchio. In Venice, walk over the Bridge of Sighs to St. Mark’s Square and the Doge’s Palace, and give in to the touristic experience of gliding in a gondola. In any of these cities, wear comfortable flat shoes and keep your wallet and documents out of range of nimble fingers. You will need to reserve in advance for tickets to major sites and sought-after hotels.

One Week

Two full days in Rome (and a one-day side trip to Pompeii), then take the high-speed train to Florence for another two days. Finish up in Venice for your final two days and then take a vaporetto (water taxi) to the airport for your flight home.

Two Weeks

Arrive in Milan and spend two days there (museums, shopping, La Scala) and a day trip north to Lago Maggiore or Lago di Como. A three-hour train ride to Venice for another two days. A two-hour train ride to Bologna for the day, then the train to Florence where you will stay two nights. Rent a car for a day’s outing to see the Tuscan countryside. Then on to Rome for three days, including a visit to the Tivoli Gardens. Down to Naples and the Amalfi Coast, including Pompeii, for your final three days before returning to Rome to catch your onward flight. (This itinerary can be reversed: Start in Rome and end in Milan so you won’t have to carry your Milan purchases with you the whole trip.) 

Three Weeks

Add to the above itinerary an additional week for Sicily. Renting a car is recommended since the countryside can be lovely and a well-marked road rings the island. From Reggio Calabria you take the ferry to Messina. Pick up your car and drive to Taormina for two nights. Visit Mount Etna if it is not smoking. Then drive to Ragusa for its local color, chic little hotels, and the best chocolate on the island (in Modica). Stop in Agrigento for the Greek temples and end in Palermo, with its shops, culture, nightlife, and thousands of ways to cook eggplant. Palermo’s airport has frequent connections to Milan and Rome. 

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