Ah, Italia! It's one of the world's favorite destinations in Europe. And one where you could go in a hundred tempting directions. So how do you design a dream vacation there? By focusing on places that capture essential elements of Italy: the magnificent architecture, the people and their romantic nature, the culture, the singular food, and wine.
You can do it in just two weeks with the following once-in-a-lifetime travel itinerary: three or four days in Rome, a week in the hill towns and countryside of Tuscany or Umbria, and three or so days in romantic Venice.
As for booking your plane tickets, hotel and tickets to sought-after tourist attractions, you should do this well in advance from home. Allow up to six months in advance: For example, you're likely to find better prices and availability in mid-winter for a trip you plan to take in June.
If you like warm weather but want to avoid the high tourist season, the optimal times to visit Italy are May–June and September–October. Also, prices tend to be lower in these months than at the height of summer. Try to book your apartment or hotel room when you book your plane ticket. If you plan on visiting a major attraction like the Uffizi Gallery in Venice, which has 10,000 visitors a day, book that early, too.
Traveling between destinations is best by car or train. If you choose to drive, check with your car rental company for the optimal time to book, but earlier is always better for Italy. Traveling by train in easy; just buy the tickets for your next destination when you arrive in a place so that you're all set when it's time to leave. Traveling inside cities can be done by public transportation or taxi. In the countryside, you'll likely need a car to shop and explore.
Start in Rome: Day 1
Rome is a fantastic starting point for this trip. For one thing, you can easily fly there from most places and you may not need (or want) a car. Plan to spend at least three or four days in Rome. Consider consulting a three-day Rome travel itinerary for ideas.
Choose a hotel that's near public transportation. Use our guide to places to stay in Rome, which includes recommendations, from budget-conscious to luxurious accommodations. If this is your first visit, you might want to choose a small hotel or bed-and-breakfast offering personalized service. A favorite is the Daphne Inn, which is especially good for your first visit to Rome. The helpful, English-speaking staff will map out your days, make restaurant recommendations and even give you a cell phone so you can call them if you get lost or need advice.
On your first day, take some time to just wander around, get used to Rome and recover from your jet lag. Choose an area near your hotel and just wander—don't worry about seeing all the tourist sites. For an overview of Rome, you can hop aboard bus number 110 (the touristic circuit) at Termini Station.
Rome: Days 2–3
Plan to spend one day touring ancient Roman archaeological sites.
Allot another day for the Piazza Navona, Campo de Fiori, Pantheon, Trevi fountain and Spanish steps (all free) and for visiting museums. You might want to walk through some interesting districts such as Trestevere, the Jewish quarter and the up-and-coming Testaccio, where you can dine on authentic Roman food.
Rome: Day 4
Tuscany or Umbria: Days 5–11
For the next part of your vacation, you'll rent a vacation house or an agriturismo (renovated farmhouse) in Tuscany or Umbria, where you can visit some great Renaissance and medieval towns, drive through beautiful countryside and experience Italian life as more than just a tourist in a hotel. Here are some resources to help you plan this leg of the journey and make reservations for a place to stay, learn how to get around and figure out what to visit.
By staying in a house for a week, you can usually save money, shop and eat where the locals do and spend time relaxing. Look for a house with a washing machine, so that you can pack light and wash clothes in the middle of the trip. You'll enjoy shopping at Italian farmers' markets and specialty food shops, and you'll be able to cook what you buy and eat at home.
You'll need to arrange your house a few months before you go. You can choose a house in a small village, in a city or out in the countryside in an agriturismo (renovated farmhouse). If there are certain cities you want to visit, be sure the house is within easy driving distance so you can get there and back in one day. In Tuscany, Le Torri vacation apartments are in a prime location between Florence and Siena. If you want to visit both Tuscany and Umbria, the holiday houses at Il Fontanaro Organic Farm in Umbria near the border of Tuscany make a good choice.
Italy's train system is inexpensive and fairly efficient. Consider taking the train from Rome to a city near where you have arranged your lodging. Then pick up your rental car, which you have also pre-arranged, and drive to your house. Consider booking a car through Auto Europe because there are no hidden (extra) charges. If you're renting a vacation apartment in a town, you may not need a car.
Most house rentals run from Saturday afternoon to the following Saturday morning. Since Italian shops are generally closed on Sundays, you will want to do a little shopping when you arrive to stock up for the weekend and at least have bottles of water and wine. Then spend a little time walking in your neighborhood.
Tuscany and Umbria are both beautiful and fairly compact, so you will be able to visit a number of places easily. If you want to visit Florence or some of the other larger cities, save yourself a little trouble by driving to a nearby train station, parking and taking the train into Florence.
Popular Tuscan destinations include Siena, Pisa, San Gimignano, Lucca, the wine towns of Montepulciano and Montalcino, the Chianti wine region, and Cortona (made famous by "Under the Tuscan Sun").
In Umbria, you can visit Assisi, Perugia, Orvieto, Spoleto, and other medieval hill towns as well as Lake Trasimeno and a few Roman ruins.
Venice: Days 12–14
After a week in your rented country house, drop off your car, and take the train to Venice. This city on Italy's eastern, Adriatic shores is a treasure, with much to see and do.
In Venice, you'll get around by walking or taking a vaporetto, a large passenger boat that functions like a city bus.
You'll want to spend at least two or three days here. Months before you leave, take a look at a Venice sestiere map and guide to choose the neighborhood where you want to stay. If you stay longer than two or three days, you may want to rent an apartment for a week in a sestiere, or local neighborhood.
While in Venice, visit San Marco square, the Rialto Bridge, and the Grand Canal. Give yourself some time to get away from the tourists and wander the back streets and small canals to get a real feel for Venetian life. Before lunch, stop in a bar and order some cicchetti (little Venetian snacks) and a glass of wine. Try a ride in a gondola.
From Venice, you can fly back to Rome or take the train to Milan and fly home from Malpensa Airport, after spending a night or two in Milan, Lake Como or Lake Garda. From here, it's easy to fly back home to the United States.