With fourteen days in Italy, you can visit all the major cities as well as some off-the-beaten-path towns and villages that most tourists never even realize exist.

Days 1–3

Start your itinerary in Venice, just as you would for the one-week itinerary, but instead of moving from there straight to Florence at the end of your second day, go instead to Milan or Bologna. If you want to shop, Milan is the place to be. If you want to see great architecture and enjoy hearty meat sauces atop pasta, then Bologna it is. Both cities are easily accessible by train, and routes are covered by a standard Eurail pass.

Days 4–5

Take a morning train to Florence. Schedule two nights' hotel here, giving you three days of touring. That way, you can enjoy the best of the city sights and take a day trip to a local village. The Tuscany countryside is gorgeous, the food doesn't get any fresher, and the wine doesn't get any better. You might even pay a visit to Montalcino, where they bottle the world-famous Brunello reds.

Days 6–7

Spend days six and seven exploring Rome and Vatican City. The train from Florence is easy, and having two days instead of one means that you won't have to fight the afternoon crowds at the Colosseum or the Sistine Chapel. Plan to spend each of your two mornings at one or the other, with the rest of your day devoted to seeing Rome's museums, archaeological ruins, shops, and trattorias.

Days 8–9

Take the train to Naples, where you will be able to indulge in a two-day stay that lets you enjoy the sights at Pompeii and Mount Vesuvius at a leisurely pace — visit one each day — followed by some tours of the architectural sights and museums within the Naples city limits during your afternoons. Two days in Naples also will give you a chance to sample multiple pizzerias in the food's birthplace, so that you can get a true taste (in every sense) of just how staunchly Neapolitans defend their thin-crust style and traditional toppings.

Days 10–11

Take the train south from Naples on the spectacularly scenic, five-hour ride to Reggio di Calabria. This is the long way to the “toe of the boot,” but it's worth the time if you can get a window seat. Have your camera ready for gorgeous coastal views. In this instance, the ride is the destination.

Once you arrive at Reggio di Calabria, you will be just across from Sicily, which is so close that you will be able to see it on clear days. Some train cars get put right onto ferries and moved over to train tracks in Sicily, while other trains force you to get off and take the ferry crossing on foot. Either way is a breeze, and you can overnight in Sicily and then spend the next day touring the island, eating veal Marsala, or simply soaking up some sunshine on the beach.

Days 12–14

Sicily might be where you want to end your two-week Italy itinerary, given how much traveling you will have already done from location to location. And there's definitely plenty to do on the island if you want to spend your last few days there.

However, if you have one more travel day in your weary bones, then consider spending day twelve or thirteen on the ferry from Sicily to Sardinia. Better yet, book an overnight trip, as the ferry ride can be long — as long as fifteen hours from Palermo, in northwestern Sicily, to Cagliari, in southeastern Sardinia. Since an overnight trip gets you into Sardinia the morning of your thirteenth day, the overnight ferry ride gives you two days to play on some of Italy's finest beaches before flying home. If you can afford it, a hotel on the ritzy Costa Smeralda, along Sardinia's northeastern shore, will offer you beachfront memories to last a lifetime.