Tips For Traveling in Italy

Getting There

Travel Agent

If you don’t have your own trusted travel agent, here is one we can recommend:

She is familiar with Il Chiostro programs and can help you with flights, hotel reservations, extensions before or after your trip, transfers, and especially booking the right travel insurance to cover your trip.

Over the last couple of years, how we travel has changed.  For that reason, we now encourage everyone to use a travel professional to help arrange your travels.  One of the most important services they can provide today is to help you choose and enroll in the right travel insurance program. With Covid and the possibility of changes and postponements of itineraries, travel insurance is all but essential.  On your own, it can be overwhelming to select the right plan from the variety available.  Also, if you confront any obstacle while traveling, a travel professional will take the stress off your shoulders and help you to navigate through whatever issues may arise.  Booking through an online site like Expedia or Hotels is convenient and possibly less expensive, but they won’t be much help if you need to alter your plans.  A travel agent, on the other hand, is there to assist you throughout your trip.

Personal Travel Insurance: however you get to us, this is strongly recommended. It protects you against costly penalties in the event that you need to cancel your trip at the last minute.  We can recommend Travel Insured International, who have a very comprehensive program designed especially for travel in these times.

Two useful resources that give you all the information you need to evaluate the policy that is right for you:

Covid Protocol-2022

At this time, restrictions have loosened in Italy and Europe in general.  The mask mandate has become voluntary in most public spaces.  Antigen tests are not required to enter or travel around Italy.  If someone is infected with Covid the symptoms are usually mild and flu-like.  Should that occur, Italy no longer requires quarantine, but only “responsible self-monitoring”.  That means you can still go about your business, but wear a mask around other people.

With this in mind in this ever-changing environment, we have nevertheless instituted these regulations and protocols to mitigate against the remaining risks associated with the pandemic:

  • Participants in our programs abroad are encouraged to be vaccinated and boosted.
  • Listen to your airline:  they will alert you to any current requirements prior to your flight.  Everyone must follow those specific regulations before boarding the plane.
  • Mask mandates are no longer required anywhere in Italy, but everyone should carry a mask with them possibly to ride in vans, public transportation and while traveling on airplanes
  • We strongly encourage all participants to have adequate travel insurance before they leave home.  We can recommend Travel Insured International (  They offer a comprehensive package designed especially for travelers in these times.
  • In these times, we recommend making your travel arrangements using a trusted travel agent.  Should there need to be any last-minute changes or glitches, the agent can handle all details.  Just call.  If you don’t have your own trusted travel agent, we can recommend:

She is familiar with Il Chiostro programs and can help you with flights, hotel reservations, extensions before or after your trip, transfers, and especially booking the right travel insurance to cover your trip.

Travel suitcase

Hints for Getting to Italy: Airfares
Most airlines have regular flights to Rome or Milan. Some have direct flights to Venice (Delta).  One little-known fact is that if you are heading to Tuscany, some airlines have seasonal non-stop flights to Pisa.  It might be worth checking that out, since it is a short train ride away from Florence, and the prices are usually more economical.  Most other cities in Italy do not have intercontinental airports. That means that to fly into Florence, for example, you will need to stop over in some other European city first.

The number of travel sites that will help you organize your airfare grows and changes almost daily.  Here are a few suggestions that we have found helpful:

  • Airfare Watchdog – Airfares in general are rising, but there are still bargains out there. Try this site that will keep an eye on the fares as they fluctuate and send you regular notices about your itinerary. It saves you time from constantly surfing the web for reasonable airfares.
  • Vayama – a new site for international flights that is easy and fun to use.
  • A fun, new site for finding airfares recommended by some travel writers is
  • will compare prices from a variety of other traditional internet based airfare locators like Priceline and Orbitz

Some other suggestions for finding the best prices:

  • Try going directly to the airlines’ websites. Check Expedia and Travelocity as a base to see what fares are going for, then go back to the airline website.  They often post discount “promo codes” on their home pages that you can use to purchase tickets. You can even Google “[airline name] promo codes” to find them.
  • Check regularly. They scan lots of sites for promotions. They often post unpublished discount codes.
  • Try to vary your departure days to travel off peak and see how that affects the price.  It also might give you to opportunity to spend a couple of extra days in Italy, “as long as you’re going…”
  • Don’t insist on flying direct. Many national airlines like TAP of Portugal offer lower fares when you stop in their hub city first
  • Look for fares to Pisa or Bologna. These are on good train lines and usually less crowded and cheaper routes.

PassportsA valid passport is essential for travel to Europe. The easiest way to renew is by mail or at a designated post office, as long as you have enough lead time. The current processing time is 4-6 weeks, expedited processing takes 3 weeks. Whether you are applying for a new passport or renewing your expired passport, this site has all the information you need.

Very Important – If your passport expires 3-6 months from your date of entry, you may be prevented from traveling abroad!  In fact, most countries require that a passport be valid for at least 6 months beyond the completion of a trip. Check your passport early and renew well in advance to avoid trouble getting on the plane.

Applying for a New Passport

This must be done in person, either at a post office that offers that service or at a US State Department office.

  • Standard Fee:  $110
  • Processing time:  4-6 weeks
  • Expedited Processing: $60 surcharge, 2-3 weeks processing time
  • Fee for Mailing Passport to you:  $25 (or you can pick it up in person)
  • Required Documents:  proof of US citizenship – your birth certificate which must bear the original embossed seal (copies are not acceptable) and a valid photo ID (driver’s license)

Renewing Your Passport

This can be done by mail if your most recent U.S. passport:

  • Is undamaged and can be submitted with your application;
  • Was issued when you were age 16 or older;
  • Was issued within the last 15 years; and
  • Was issued in your current name or you can legally document your name change with original or certified copy of your marriage certificate or the government-issued document evidencing your legal name change.

For more passport info visit:

Keeping track of your passport, travel documents and cards is also important while traveling. Here are some tips from one of our instructors, Rebecca Zdybel (Eat, Paint, Cook Tour of Tuscany).

  • Make a photocopy of your cards, passport and ID before you leave and put them in your carry-on.
  • When you arrive at the hotel, put them in the safe so you have access to information in the event of theft.
  • Contact  credit card companies before you leave to tell them the dates and places you’ll be traveling abroad.  It avoids fraud protection issues that can impact your ability to use the cards while traveling.  (God forbid we can’t spend money!)
  • Check to see if your card charges foreign transaction fees.  Ask your credit card representative.  If you will be charged fees,  think about getting a card that doesn’t charge foreign transaction fees.  Barclay and also Bank of America both offer them.
  • Bring medical insurance cards and your healthcare savings credit card if you have one.
  • Always keep your passport in your hand…do not set it down or let it go out of your sight with employees of any restaurant or rental companies.  Hotels sometimes keep your passport on tours, and though this really bothers me, I will cooperate if they insist. .
  • Consider money belts or bra-wallets to increase the safety of your cash, cards and identification.
  • Keep your paperwork together and secure:  I generally make a manila envelope as my travel file.  I keep my boarding pass there, and I put copies of my itinerary there and any travel emails sent to me by my carriers or travel companions.  That way I have one place to look when I want to refer to travel arrangements.  I keep this with me while I travel in my carry-on.  I also make a copy for my husband to keep at home if he’s not traveling with me.

Hotel bedIf you plan to spend some time in Italy before or after your time with Il Chiostro, you will need to book your hotel or pensione in advance. There are many options beyond the large chains and the places recommended by the popular tour guide books. Click on one of the links in our Places to Stay in Italy section at the top of this page to get a list of places recommended by previous Il Chiostro participants. And if you have a good experience at a place not on our lists, we are always pleased to add new locations.

There are also many web sites that help you search for unique, economical places to stay.  Some recommendations:

If you are staying in one city for at least 3 days, consider renting an apartment rather than spending the money on hotel rooms, especially if you will be sharing with other people. There are a host of rental sites on the internet. Here are just a few:

However you get to Italy, there are several internal travel options, from trains and buses to car rentals.

boarding a trainTrains: a wonderful thing about Italy – and Europe in general – is that almost every city and town can be reached by the fairly efficient system of trains that traverse the country. Some important notes about train travel:

  • For up-to-date fares and schedules check the Italian National Train Service web site (in English, mostly) or try the North American web site dedicated to train travel in Italy:
  • When arriving at the airport in Rome (Leonardo da Vinci, or Fiumicino) there is a train that connects directly to the center of the city – the Leonardo Express. Just follow signs for Treni/Trains when you clear customs and enter into the terminal. The trip takes about 40 minutes and trains leave about every half hour. Only two trains leave from this station: one for Termini, the main station in the center of Rome, the other for Tiburtina, a secondary station a bit outside of the center. (If you are connecting directly to the SENA bus to Siena, you will want to go to Tiburtina.)
  • Many smaller stations (like Siena) do not have elevators or escalators so be prepared to haul your luggage up and down stairs to get to your track
  • Important! You must validate your ticket in one of the green or yellow machines before getting on the train. Failure to do so will result in a heavy fine, payable on the spot. If you find that you have boarded a train without stamping your ticket, you should go immediately to the conductor, tell him/her that you forgot to validate your ticket and have them hand cancel it
  • It is no longer possible to buy a ticket on the train. You must board a train with a ticket or incur heavy fines
  • Refrain from putting your feet on the seat opposite you. Italians frown on this behavior. You risk being scolded by the conductor.
  • Reservations (prenotazioni) are not required, but recommended for many of the more popular routes. Note that there is a distinction between buying a ticket and reserving a seat.  Having a ticket does not automatically guarantee you will have a place to sit down and trains are often oversold so people end up standing the entire journey.  Especially if it is a longer trip, reserve a seat (with a specified carriage and seat number) when you buy your ticket.
  • Most stations today have automatic ticket machines, with instructions in English. They take cash or credit cards. They will also tell you the schedule for your train. Use these to avoid the long lines and language barriers at the ticket counter (biglietteria)
  • You can book trains ahead either through or

Buses: this is a viable alternative to trains. Intercity buses are comfortable, often faster than the trains and have a place to stow your luggage underneath so you don’t need to drag your bags through the aisle and hoist them over your head onto the rack (which is usually too small). Some important notes about traveling by bus (pullman):

  • There is a quick and efficient system serving Florence and Siena called SITA. We recommend taking the RAPIDA between these cities. For fares and schedules:
  • There is also a convenient bus between Rome and Siena. This is a 3hour, non-stop trip. In Siena the bus stops at either the train station or the center of the city. In Rome the bus stops at the Tiburtina train station, a bit outside of the center, but convenient for connecting to the airport.  For fares and schedules: Sena Bus Lines
  • From the Florence airport there is a frequent shuttle called Volainbus that takes you into the center of Florence. Tickets cost 5 euros and can be purchased on board.

driving a car2Car Rentals: if you want to put yourself behind the wheel, there are many options.  First, be aware that most rental cars are standard transmission. There are a few automatic cars available, but you must reserve these ahead of time and they are more expensive. Also, gas in Europe is very expensive! Ask for diesel – it is cheaper at the pump and lasts longer.
We suggest you organize your car rental before you leave home.  Use one of the major companies:  Hertz, Avis or AutoEurope.  Or try this new website from Expedia dedicated to renting cars: They are showing some very competitive prices for cars in Italy using major rental companies.

If you rent a car, beware:  there are hidden cameras on the highways to check your speed and in the historical centers of most towns regulating access to restricted areas. For any traffic violation, the cameras will record your license plate and send the bill to your rental agent who will in turn send you a bill for your infraction. That bill will arrive about 6 months after the fact when you probably won’t even remember speeding or driving into the center of a restricted town. Your rental agency will automatically tack that amount onto your credit card on file. These charges are difficult to fight, so please try to stick to the speed limit and stay out of the historic centers of towns.

For driving directions to any of our locations, send us an email and we’ll email you a printed copy in English.

Car Services: if you would like to arrange for a private car service to pick you up at the airport or your hotel and take you to your Il Chiostro workshop we can arrange this for you.  Just give us a call or send an email with your request.  If you can share the cost with others, the cost becomes more reasonable.  These cars are professional and reliable. Payment can be made directly to the driver in either cash (euros) or by credit card.

Travel Tips

We at Il Chiostro subscribe to the Slow Travel philosophy.  Like the Slow Food movement, this means taking your time to appreciate all facets of the place you are exploring.  This includes eating the local food, drinking the wine of the area and adhering to the timetable of the culture.  Suggestions about how to travel slow:

  • Unplug – this might not be entirely possible given the electronically connected world we live in, but limiting your time on social media can help you enjoy your trip for yourself instead of constantly trying to interpret it for others back home.  It’s important to
  • Be where you are – the more you can let go of your own habits the more you will be able to recognize the cultural differences before you.  Pay attention to how a day unfolds in this new place, listen to how people interact, watch what is happening around you without trying to take control.  And always remember
  • You are a guest in their country – learning a few courtesy words like grazie, per favore and prego can help in all social situations.  Try to be polite when you don’t understand something and always assume that the native knows how things work in his country better than you do.  “When in Rome…”

And if you are planning to spend a few days in Rome, either before or after your workshop, you might consider booking a personal tour with our friends Antonio and Paolo at Roam Around Rome.  Whether this is your first time or you have been to Rome many times before, they will customize your visit around your interests.  Il Chiostro clients are eligible for a discount.

Money, Money Money

The Exchange Rate:  A vacation to Europe this year can be quite affordable.  It’s all about the exchange rate, which is pretty favorable to Americans this year. Check out the Currency Exchange Rate to know how much your dollar is worth abroad.  As you travel the rate can fluctuate.  When you take out money from an ATM or pay with your credit card, you will be given the most current exchange rate that day.

Credit Cards:  before you travel, get a card with No Foreign Exchange Fees.  Capital One was the pioneer in this area, but now many other banks offer this service.  It can really save you a lot of money when you get home and get those bills if there isn’t an additional fee tacked onto each sale made in Europe.  In any case, make sure you call your credit card company before you leave home and tell them that you will be traveling abroad, so that they don’t put a stop on your card for security reasons.  It can be embarrassing when you are about to buy that gold necklace on the Ponte Vecchio and your card doesn’t go through!

“Would you prefer to pay in Euros or Dollars?”:  this is a question often asked when you are paying with a credit card in Europe.  Although having the price immediately converted to a currency you understand ($$) sounds convenient, this option is rarely beneficial.  In our own studies we have found that the exchange rate the store (or hotel or restaurant) gives you is not as good as the one your own bank will use.  And paying in dollars doesn’t necessarily avoid the foreign transaction fees either.  Best pay in the local currency (euros) and have your bank perform the exchange.

Getting Money:  the easiest way is to use your ATM card in one of the many locations in towns and cities across Europe.  Note:  this is different than using your credit card to get a cash advance which comes with heavy interest fees.  When you use your ATM card (don’t forget your PIN) it comes right out of your bank account back home, but in euros.  No interest fees, no waiting in lines, and these are typically very secure.

Bringing Cash:  this is a less efficient way to travel.  Bringing American dollars is inconvenient:  no one will take American dollars in Europe, so you will have to find somewhere to exchange them for euros.  That means either waiting in line at a bank or using a touristy cash exchange office.  Both of these will tag on hefty service fees and probably not give you the best exchange rate either.
Some people like to get euros from their bank before they leave for Europe.  This is good in the short term, to ensure that you have some cash for a cab or a tip, but don’t buy a lot of euros in America.  The exchange rate is not favorable and the bank will again attach fees for this service that isn’t worth it.  There are ATM machines in most airports and train stations so that when you arrive you can immediately get cash in the local currency.

“Can I send my art supplies (heavy shoes, clothing, etc.) ahead of me?”

Obviously this will reduce the weight of your suitcase, but it will also probably reduce your painting time in Italy because most likely your supplies won’t arrive in time.  What your shipping company in the US doesn’t tell you (perhaps because they don’t know) is that customs in Italy is very strict.  They usually stop these shipments when they enter the country to determine if the goods are meant to be sold in Italy – even if the sender clearly states that these are personal materials for personal use. In order to clear customs they  require a written statement from you, the shipper, declaring that you don’t intend to set up business in Italy with your supplies along with your passport information.  All of this usually delays the materials beyond the start – or even end – of the workshop.  On top of that, typically apply an import duty onto the materials over and above whatever the shipping agency has already collected. They will arrange for courier to deliver the goods to you, but require payment upon receipt.  If you have already left the country they will not ship everything back to you.

So although in theory it would be more convenient to ship, in reality the materials probably won’t arrive in time and when they do there will be a hefty surcharge that would probably cover the cost of buying things in Italy (which I guess is their point, ultimately).

You can bring paints (not turpentine, which we will supply) on the plane in your checked luggage.  A small quantity in 3oz. containers of paint can even go in your carry-on luggage.

Please Don’t Order a Latte

Cappuccino, photo by A. Holtzman

More than once I have witnessed the bewilderment on the face of an American when the waiter at a cafe delivers with a flourish a nice tall glass of milk.  What they really wanted was a coffee, but latte in Italian means milk.  Caffe latte would be the proper term for what they wanted.  Coffee is a way of life in Italy with myriad variations.  Herein is a partial list:

  • The basic unit of coffee is un caffè (what non-Italians but no Italians call an espresso*)
  • caffè ristretto – a caffè with only half the amount of water squeezed through the espresso machine, but through the same amount of coffee grounds
  • caffè lungo – a long coffee – a caffè with double the water of an ordinary caffè
  • caffè doppio – a double espresso with twice the amounts of water and coffee grounds
  • caffè macchiato – a stained coffee – add a drop of milk to a regular caffè
  • cappuccino – caffe hooded with milky foam
  • cappuccino senza schiuma is literally a cappuccino without foam
  • cappuccino chiaro – a light-colored cappuccino with less coffee and more milk
  • cappuccino scuro – a darker brew with more coffee and less milk
  • caffè e latte – a milky coffee with more milk than any cappuccino and no froth
  • latte macchiato –  a lot of milk with a stain of coffee
  • caffè al vetro – if you should choose to drink your coffee from a small glass instead of a thimble-size cup
  • caffè corretto – usually a normal caffè with a generous lacing of grappa or any other liquor of your choice

* NOTE: there is no “x” in the word espresso, no matter how they pronounce it at Starbucks.

Keep to the Schedule

The days in Italy, after centuries of evolution, are constructed differently than they are in America.  The differences are subtle, but worth noting.  Most Italians start their day early with a quick cappuccino and a coronetto at the corner bar (cafe).  Then they go about their morning activities until around noon when they break for a good lunch.  Restaurants keep specific hours and are rarely open throughout the day.  If you arrive outside of those hours either they won’t serve you at all, or you’ll get whatever is leftover in the kitchen.  In the later afternoon, around 5-6pm Italians enjoy what they call the passeggiata – a lively stroll through the streets with friends (usually arm-in-arm) for window shopping, a gelato, a glass of pro secco at a cafe.  It is an activity that goes to the heart of Italian life:  a time to dress with style, to see what’s going on and to be seen by people in town.  It is a time filled with casual encounters, the latest fashion and joyful relaxation.  After that the dinner hour starts, but most restaurants won’t open up until 7pm with the clients sauntering in around 8.  Once you have a table no one will hurry you away – the table is yours for the night to enjoy your meal, your coffee and linger over a grappa or limoncello unhurried.  Often the owner of the restaurant will drop by your table to see how things are going.  Then it is time to head home and start the whole civilized process all over again.

If, as a tourist, however, you decide to sleep in and linger over a big breakfast, chances are that you will be out of step for the rest of the day.  The shops or galleries you intend to visit will be closed by the time you get there.  You’ll wander around frustrated until about 2 when you will search for lunch.  Most places will be closed so you’ll end up eating a slice of pizza on the curb.  After wandering around a little more you’ll decide you are tired and go back to your hotel for a rest before dinner.  By the time you re-emerge for dinner the streets will be scattered with the last vestiges of locals saying “Ciao” after finishing their social passeggiata.  You’ll arrive at a restaurant before the dinner hour gets going and leave when the locals are just settling in for a fun evening.  Then you’ll get to bed early wondering “what’s so special about life in Italy??”

Places to Stay While in Italy

If you plan to spend some time in Italy before or after your time with Il Chiostro, you will need to book your hotel or pensione in advance. There are many options beyond the large chains and the places recommended by all of the popular tour guide books. Click on one of the links below to get a list of accommodations recommended by previous Il Chiostro participants. And if you have a good experience at a place not on our lists, we are always pleased to add new locations.  Buon viaggio!

One suggestion for authentic accommodations in very clean, well-located convents and monasteries might be Monastery Stays.  The church always had the best real estate in any town or city in Italy.  These have been converted to guest houses or bed and breakfasts

Click on a location below to find your hotel, B&B, monastery or pensione:

Accommodations in
Florence and Siena
Accommodations in Milan
Accommodations in Rome
Accommodations in Venice