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A perfect two-week itinerary in Italy that includes just about everything: Rome, Florence, Venice, Tuscan & Umbrian hilltowns (including Siena, Pisa, and Assisi), the Amalfi Coast, Pompeii, the Cinque Terre, the Italian Lakes, and Milan
Here is an itinerary that takes in Rome and Pompeii, Florence and the hilltowns of Tuscany (Siena, San Gimignano, the Chianti, Pisa, Monteriggioni) and Umbria (Perugia, Assisi), the Cinque Terre fishing villages at the tip of the Italian Riviera and the city of Milan, Venice and Verona, Lake Garda and Lake Como.
This is the quick, just-the-facts-ma'am version of the itinerary, laid out as if on a calendar (which is why the "Day 1" is placed where Saturday would be, assuming most folks will be flying over to Italy on a Friday night; click here for more such foolish assumptions about how these itineraries work).
If you want a longer, text version of the daily plan—complete with transportation details and descriptions of (and how much time to spend at) each of the sights and destinations, click on either the "Day #" at the top of any given day or the "» more" at the bottom. (Or you can just scroll through the whole thing at once on this page.)
I'm all for planning your own trip‚ and this website is set up to help you do just that—but some people might just as well prefer to leave all the planning, logistics, transportation, lodging, and gathering of information to the professionals and simply sign up with a guided tour.
Nothing wrong with that. Just take my advice and choose a tour that emphasizes small groups over large crowds, local transport over big tour buses, and fun cultural experiences over sightseeing checklists. You'll have a better time, and probably spend less for it. Here are a few of my favorite tour companies who emphasize just that.
Lodging: Booking.com, Bedandbreakfast.com, Airbnb.com, Rentalo.com, Vrbo.com, Belvilla.com, Hostelworld.com, Hostelbookers.com, Couchsurfing.com, Homeexchange.com
Packages: SelectItaly.com, Gotoday.com, Orbitz.com, Expedia.com, Travelocity.com
Maps & guides: Amazon.com, Maps.google.com, Tuttocitta.it
A tall order for just two weeks? You bet. But there are three tricks to fitting all you can into such a short time here.
Don't forget to pay attention to the "What to do before you leave" section (next) covering all the details you need to take care of before leaving home—and be sure to read the "Foolish Assumptions" page about how these itineraries are meant to work.)
The basic itinerary above is pretty packed—a lot of early morning wake-ups, a lot of churches and museums—because there's simply so much to see and do in Italy.
By all means, feel free to prune this itinerary down to something a bit slower paced if you don’t want to spend so much time running around (say, leaving out a few hilltowns—Pienza or Orvieto—or perhaps the Cinque Terre, or maybe Pompeii). I've even gone ahead and whipped up a sane version of this itinerary that leaves out Pompeii and the Cinque Terre.
Think of this more as a blueprint to squeezing in the maximum possible. You should, above all, have fun.
I will freely admit to being as guilty as anyone of this, but: Please try not to overplan your trip to Italy. That's a two-fold plea:
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Lodging: Booking.com, Bedandbreakfast.com, Airbnb.com, Rentalo.com, Vrbo.com, Belvilla.com, Hostelworld.com, Hostelbookers.com, Couchsurfing.com, Homeexchange.com
Packages: SelectItaly.com, Gotoday.com, Orbitz.com, Expedia.com, Travelocity.com
Maps & guides: Amazon.com, Maps.google.com, Tuttocitta.it