This article originally appeared in the October/November 2022 issue of Dream of Italy.
An extended stay in Italy leaves room for magic to happen. With time to wander, Italy undoubtedly will amaze you and reveal parts of itself you never could have imagined. Of course, some planning is inescapable for an extended stay abroad, but we encourage you to leave room for serendipity.
The events of the last few years have brought both a hunger to get out and live and more flexibility in our daily routines. For those who are running our own businesses or working remotely, a great Internet connection may be the only requirement to trade in views from our office windows for views of the Dolomites or Duomo.
Note that technically Americans may stay in Italy up to 90 days out of every 180 days without more than the automatic tourist visit, but cannot work. That said obviously many of us even on vacation in Italy find ourselves spending time on our computers. Stay tuned as Italy is trying to introduce a one-year digital nomad visa, which will officially allow remote work.
In this newer effort of work/life balance, many are now taking a “sabbatical” between jobs and some companies even offer extended time off after you work for a certain number of years. Of course, those who are already retired have even more flexibility.
How many of us have a dream of living in Italy permanently? Extended stays are one way to help satisfy that dream or even test the waters before a permanent move. Here are some tips and ideas for planning a longer stay in Italy:
Create a Vision, Pick a Date and Save Up
Let’s face it. Italy is overwhelming. It is impossible to do everything with any amount of time in this country. So where do you start with what makes sense for your extended stay? Narrow it down. Decide on a theme or a purpose for your time. Be sure to write it down as something of a mission statement.
Do you want to see every Caravaggio in Rome? Plan to spend your days in a quiet villa writing a novel? Are you going to Italy to learn the language? Who do you want to be at the end of your sabbatical? What do you want to have accomplished?
When an idea comes up, ask yourself if it fits your vision or mission statement. That will help you refine your plans.
When I interviewed Frances Mayes for our Dream of Italy: Tuscan Sun Special, she shared how she found that women especially “come to Italy on a quest.” Man or woman, what’s your “quest”? Italy is a “catalyst” that makes you feel “encouraged in whatever you want to do,” Frances told me.
That’s all fine and good but once you have a mission/theme/purpose defined how can you make it happen practically? New York Times 10-time best-selling author David Bach who has dedicated his career to helping people obtain financial freedom and “live rich now” told me about planning his own “radical sabbatical” with his family in Florence with the simple instruction: “Pick a date.” “It could be three years from now, four years from now, five years from now, and then you work backwards.”
His next piece of advice: “Open a dream account.” “This is an account that literally you put money in from every paycheck” to realize your extended stay or move to Italy.
As for David and his family, they planned a one-year sabbatical to take a break from work, live in Florence and enroll their sons in the English-speaking International School of Florence and three years later they are still there!
Stay in One Place or Travel Around?
Creating a homebase in Italy, for instance, renting an apartment in one town for the entire time can make for an easier and deeper transition to Italian life, especially if you are bringing kids or pets or both.
Italians are such warm people and if you stay in one place, you will quickly become part of the community. This is especially true in smaller towns and villages. Frances Mayes calls the town piazza as “the living room of Italy” as the place to meet and greet.
“We tell our participants to choose a bar. The first day they will ask you what you want to have, the second day they will ask you once you want to drink, the third day they will ask you your name and they will tell you ‘okay, do you want the same?’ because you will be part of that neighborhood,” says Francesca Donati of Road Scholar who runs their Living and Learning in Florence program.
If you have Italian blood and are curious about your Italian heritage, you can take this time to discover your roots by staying in your ancestral hometown. If it’s a small town, chances are it will be quite affordable. Not lonely will you learn about your genealogy but local lore and family recipes. That’s a very personal sabbatical. As you likely know, tracing your Italian roots may also lead you to be able to claim Italian citizenship jure sanguinis.
There’s also freedom and excitement to visiting multiple locales, which can bring unexpected surprises. Dream of Italy fans Martha and Greg Henze who spent seven months in Italy on sabbatical really took this chance for adventure and exploration to heart, so much so I thought they deserved their own article. While traveling they used their hobbies and interested, a network of agriturismi and the weather (“following the sun”) to help them determine where to go.
Be sure to take weather and seasons into account when looking at locations. You might love a certain town in Tuscany in the summer when it is warm and there are lots of activities but if you’re planning a winter sabbatical, do some digging if things will be open. You can find mild or intense for any season, for example, a winter spent skiing in northern Italy or a warmer winter in Sicily. In fact, October and November can be perfect in many southern locations, warm enough for the beach but the crowds are gone.
Transportation is an important consideration. Within cities and connecting among cities, Italy’s public transportation is quite good. Yet many areas of Italy are remote and a car is necessary. Sometimes even if you are not going to use the car everyday, a longer-term lease is worth it. Auto Europe offers brand new leases for cars to non-European Union residents for up to 90 days at rates much less than regular rentals. There are also local rental companies that have cheaper rates.
Take the Kids and Dog, Why Not?
Many families with children will plan their stays in Italy during summer months to coincide with summer break. Though one of our favorite families who home schools their kids in Canada takes them to Italy once a year during the school year and incorporates visits to museums, artisans and food producers into their school lessons. Those who really want to go all out for a family experience can plan to visit Italy for an entire school year (most often this can be accomplished with an elective residency visa
Jenni Burke, a literary agent from Oregon, has taken her young children to Tuscany for extended stays twice. She has always found Italy very child-friendly has always found her family welcomed with open arms by locals in the villages where she rented via Airbnb.
On one trip when her son was five years old, local kids would show up at their door to invite him to play soccer in the piazza. Now Jenni always suggests packing a soccer ball since it is “universal language” all kids speak and a great way to meet other kids.
To ease the transition of the jump to Italy, Jenni says to “really think about a rhythm for your family that works well for you at home and how you can implement that into your vacation” but to welcome the Italian influence on your schedule.
Jenni implores families visiting Italy to “flow with the differences” and not to be thrown off if, for example, your kids might be up until 10 or 11 p.m. at night like is typical of Italian kids in summer. She highlights how important it is to “pay attention when people are out and about.” If you are in Italy in the summer, no one will be outside playing at midday, it is simply too hot! Visit a playground in the mornings or early evenings to connect with other parents. Wait for the evenings and go for a gelato and hang in the piazza with everyone else.
What about the furry members of your family? I just took my wire fox terrier, Phineas aka to Italy for a two-month stay in Italy (we actually moved around quite a bit but he loved the action) and the trip was amazing. You truly meet everyone when you have a dog. Most hotels and rentals (though a bit less so in the south) welcome pets. Even better, you can bring a well-behaved dog inside most rest stops, restaurants, supermarkets and stores. When I had to bring Finney to the veterinarian, I was beyond impressed by the expertise of the English-speaking vet, his care and especially the bill which was $150. For all the tests Finney had that would have been at least 10 times the price in the U.S.
Tap Into Local Connections
This can’t be said strongly enough: so much of what happens in Italy is based on relationships or who knows someone who knows someone. If you have contacts in Italy, even if it is just the tour guide from your last trip, drop them a note about your upcoming extended stay. Italians love to help and connect people. While you can certainly use Airbnb.com or a villa rental agency, you might be amazed at how you can often find a well-priced short-term rental on a word-of-mouth basis.
If you can afford to take a short scouting trip (airfares are much cheaper in the winter), you can go to the area you might like to stay and look at rentals but also let locals know what you are looking for. Business is very much done face-to-face in Italy. Now there is always a risk in not using an agency in case something goes wrong so this very much depends on your risk tolerance and strength of connections.
More and more travel planners including the Dream of Italy Travel Service and local Florentine company ArtViva are expanding into planning extended stays sabbaticals. Rose Magers of ArtViva offers services including connecting to a local lawyer (for rental contracts and visas), scouting of potential rentals and advice on local life available on an hourly rate. “Stress adverse travelers or those who are planning a long or luxury stay should consider investing upfront” in these services, Rose says. Then then you can just concentrate on the dream or mission you have for your extended stay.
Organized Options
If all of the planning seems too much, definitely read on to our next article about more organized ways of planning an extended stay from pre-planned culture/co-working stays to planning your stay around attending Italian language school or training to receive a TEFL (Teaching English as a Foreign Language) certification.
One advantage of attending Italian language school is that you may be able to get a one-year student visa. You must enroll in an accredited language school and you will likely be asked to show proof that you are already taking lessons at home. A student visa does allow you to work for 20 hours a week.
No matter what you plan to do or how long you can stay, an extended stay in Italy is sure to open your eyes to new possibilities.
—Kathy McCabe