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Timeline to a Well-Planned Vacation

Timed Tips for planning a vacation to Italy you won't forget

6 Months Before You Go

Dream of Italy Time

This is where you get to go wild. Do you want to do the big three, Rome, Venice and Florence (plus the standard add-on Cinque Terre)? Or do you wish something more challenging? Calabria perhaps? Check our Maps Index and go crazy, or just look at the Italy Cities Map. Also, this is the time to think about learning some Italian, at least the "polite" words that open doors. If you want some suggestions while you're travel planning, sign up for our free newsletter. And finally, if you don't have one, think about applying for a passport.

3 Months Before You Go

Airfares and Walking Shoes

Which Italian airport are you thinking of arriving at? Make sure there is a reasonable flight there and start to think about buying your tickets (some say 4 months in advance of your trip is best). Remember, stopovers add a whole lot of time to a long trip. If you're returning to the US, you'll have to take your baggage off the plane and go through customs at your first point of entry, then lug that baggage to your next gate. Italian cities tend to be walkable, and the countryside offers lots of opportunity for trekking, so get yourself some sturdy, comfortable walking shoes and break them in. You also may wish to throw some Learning Vacations into your Italian Itinerary.

Two Months Before You Go

Choose Lodging and Transport

Will you stay in a hotel, agriturismo (farm stay) or a rental house or apartment? We recommend that if you stay three weeks in Italy, you spend the central week or so in a vacation house or apartment, using it as a hub for your Italian exploration for that week. Get a place where you can wash clothes and you'll be able to shrink your baggage. Also, will you travel by train or car? Do you need a rail pass? Will you rent or lease your car? 

A Month Before Departure for Italy

Essential Stuff!

Here's where you need to get your travel things together. Camera for those artistic selfies (we recommend this one if you're looking to buy one), luggage you can live with, and money (get 100 euro in advance to use at the airport if you want your vacation to start right away). You might consider Travel Insurance as well.

A Few Days Before You Go

Besides Fretting...

Be sure to tell your debit and credit card companies you'll be in Italy if they require it. If you don't, some companies will let your first transaction through, usually, but then they'll likely think your card might be stolen and cut you off. If you have medications that might run out, write down all their details. An Italian pharmacy (farmacia) will usually honor your perscription if they can figure out their version of you meds. Read about dealing with medical emergencies in Italy. Remember to pack light (we roll our clothes rather than lay them flat). Don't forget your battery chargers and plug converters...and have a great trip

Know Before You Go!

Information about how to call an ambulance, going to the emergency room, and how to get medication at the pharmacy: Medical Emergencies in Italy.

First of all, never carry your passport or anything valuable in your backpack where you can’t see it or in your purse. Don’t carry your wallet in your back pocket. In a big city or crowded tourist area carry your passport, extra cash, and debit and credit cards in a pouch underneath you more

Yes, no and the "polite" words will get you some respect--and can open more

If you carry a valid US passports you can stay in Italy on vacation for 90 days out of 180 days. You cannot leave and return to "reset the clock" more

The dangers of an Italian city are different than the dangers in a U.S. city. You probably won't get shot in Italy, but the likelyhood of getting pickpocketed is much greater. There are things you can do to keep you from doing paperwork in an Italian police station, of more about travel safety

There's decent access to the Internet in Italy, but like everywhere there are folks who want to steal your data. Also, if you rely on interactions with government or health websites, you might no be able to access them from an Italian IP address. There are ways to fix more

Of course, these are rough guidelines on how to plan a vacation in Italy. Work at your own pace. Don't plan to do too much that you haven't time for those little surprises that pop up. Below are some destaination suggestions. Above, linked in the toolbar is a list of Italy's top regions to visit. Have fun planning your Italy Trip. 

Italy's Big Three


Rome and the Vatican

Did you know you can save money in Rome by staying just north of the Vatican? Or, you can follow the crowd and head for Trastevere.

venice grand canal


Everyone's favorite watery wonderland. Each of the six Sestieri (neighborhoods) have their specific charms and tourist attractions

florence, italy


Like the other two of the Big Three, Firenze has its charm and overcrowding. When it gets to you, head easily by train to Lucca or Montecatini Terme

Smaller Places in Italy We Like

pitigliano, tuscany, italy


A great town in southern Tuscany to spend a few days. Walkers will like walking the "Etruscan Ways" called the Vie Cave

matera, basilicata, italy


Matera's cave houses were once the hovels of the poor. Now people make the trek to Basilicata just to stay in one. 

sulmona, abruzzo, italy


This town in the Abruzzo is said to be its prettiest, and in the spring the mountainous eye candy is wonderful.

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