Planning Your Trip to Italy

To plan your trip, you’ll need to design your itinerary—choosing where and when to go, how you’ll travel, and how many days to spend at each destination.


  • Choose your top destinations.

My recommended itinerary gives you an idea of how much you can reasonably see in 21 days, but you can adapt it to fit your own interests and timeframe. If you like Renaissance art, linger longer in Florence. Exploring Italy’s hill towns could soak up a week. For mountains, make tracks to the Dolomites. And if you’ve always wanted to ascend Pisa’s Leaning Tower, now’s the time for the climb.

  • Decide when to go.

Peak season (roughly May through October in the north, and May, June, September, and October in the south) comes with hot, sunny weather and often terrible crowds at the most popular destinations.

The heat in July and August, particularly in the south when temperatures hit the 90s, can be grueling. Fortunately, most midrange hotels come with air-conditioning. August is also the month when many Italians take their summer vacations; big cities tend to be quiet (with discounted hotel prices), but beach and mountain resorts are jammed (with higher hotel prices).

Day Plan Sleep in
1 Arrive in Milan Milan
2 Milan to Lake Como Varenna
3 Lake Como Varenna
4 To Dolomites via Verona Bolzano / Castelrotto
5 Dolomites Bolzano / Castelrotto
6 To Venice Venice
7 Venice Venice
8 To the Cinque Terre Vernazza
9 Cinque Terre Vernazza
10 To Florence via Pisa Florence
11 Florence Florence
12 Florence, late to Siena Siena
13 Siena Siena
14 To Assisi Assisi
15 To Orvieto and Civita Orvieto
16 To Sorrento via Naples Sorrento
17 Capri Sorrento
18 Amalfi Coast Sorrento
19 Morning to Rome via Pompeii Rome
20 Rome Rome
21 Rome Rome
22 Fly home  

Notes: If you have less time, drop the Dolomites, because they’re out of the way. With extra time, slow down, or add more hill towns; they’re worthwhile to visit, though time-consuming to connect by public transportation.

To modify for drivers: Tour most of Italy by train, then use a car to explore a region or two (even if it means backtracking a few hours by train or car). These sights are easier by train than by car: Venice, the Cinque Terre, Florence, Rome, and the cluster south of Rome (Naples, Pompeii, Sorrento, Capri, and the Amalfi Coast). Drivers will find a car most helpful for exploring the hill-town region. Major car-rental agencies have offices in many towns.

Winter offers cooler temperatures (dropping to the 40s in Milan and the 50s in Rome) and fewer tourists, except on major holidays. In winter, expect shorter hours for sights and fewer activities. Beach towns are nearly shut down and battered by waves; skip the Cinque Terre and Amalfi Coast.

  • Connect the dots

Link your destinations into a logical route. Determine which cities you’ll fly into and out of. Begin your search for transatlantic flights at

Decide if you’ll travel by car, public transportation or a combination. A car is particularly helpful for exploring the hill-town region (where public transportation can be sparse), but is useless in big cities (park it). Trains are faster and more expensive than buses (which don’t run as often on Sundays).

To determine approximate transportation times between your destinations, study the driving chart in the Practicalities chapter or train schedules ( Compare the cost of any long train ride in Europe with a budget flight; check for intra-European flights.

  • Write out a day-by-day itinerary.

Figure out how many destinations you can comfortably fit in your timeframe. Don’t overdo it—few travelers wish they’d hurried more. Allow enough days per stop (see estimates in “Italy’s Top Destinations, earlier). Minimize one-night stands, especially consecutive ones. It can be worth taking a

late-afternoon train ride or drive to get settled into a town for two nights. Include sufficient time for transportation; whether you travel by train or car, it’ll take you a half-day to get between most destinations.

Staying in a home base (like Florence or Sorrento) and making day trips can be more time-efficient than changing locations and hotels.

Take sight closures into account. Avoid visiting a town on the one day a week its must-see sights are closed. Check if any holidays or festivals fall during your trip—these attract crowds and can close sights (for the latest, visit Italy’s tourist website, Give yourself some slack. Every trip, and every traveler, needs downtime for doing laundry, picnic shopping, people-watching, and so on. Pace yourself. Assume you will return.

Trip Costs Per Person

Run a reality check on your dream trip. You’ll have major transportation costs in addition to daily expenses.

  • Flight: A round-trip flight from the US to Milan or Rome costs about $1,000-2,000, depending on where you fly from and when.
  • Public Transportation: For a three-week trip, allow $550 for buses and second-class trains ($750 for first class). You’ll usually save money buying train tickets in Italy, rather than buying a rail pass before you leave home. In some cases, a short flight can be cheaper than taking the train.
  • Car Rental: Allow roughly $250 per week, not including tolls, gas, parking, and insurance (theft insurance is mandatory in Italy). If you need the car for three weeks or more, leasing can be cheaper.


Budget Tips

You can cut my suggested daily expenses by taking advantage of the deals you’ll find throughout Italy and mentioned in this book.

City transit passes (for multiple rides or all-day usage) decrease your cost per ride.

Avid sightseers buy combo-tickets or passes that cover multiple museums. If a town doesn’t offer deals, visit only the sights you most want to see, and seek out free sights and experiences (people-watching counts).

Book your rooms directly with the hotel. Some hotels offer discounts if you pay in cash and/or stay three or more nights (it pays to check online or ask). Rooms cost less outside of peak season (roughly November through March). And even seniors can stay in hostels (some have double rooms) for about $30 per person. Or check Airbnb-type sites for deals.

It’s no hardship to eat cheap in Italy. You can get tasty, inexpensive meals at delis, bars, takeout pizza shops, ethnic eateries, and Italian restaurants, too. Cultivate the art of picnicking in atmospheric settings.

When you splurge, choose an experience you’ll always remember, such as a food-tasting tour or a gondola ride. Minimize souvenir shopping—how will you get it all home? Focus instead on collecting wonderful memories.


This is why everyone should visit Italy !

This is so Important for Everyone Planning a Trip to Rome!