There’s a chill to the morning, the sun lazy in burning off a cloak of fog coating the plains of Valdichiana. Boo, my sweet co-pilot and dog, awakes me at 7, tail wagging, nose pressed to my face, a paw on my chest, oblivious to the shortening of the days. His internal clock is superior to mine. I glance out my second floor window at Camucia, the town a ghost-like apparition a few miles below my hillside perch. I smell coffee, then hear my recent houseguests stirring. Another day in Paradise has officially commenced.
Cortona, in the heart of Tuscany, where I call home, is the ideal launchpad for exploring Italy. Armed with a tank of gas, GPS, and a pouch filled with one-and-two euro coins for parking, you can day trip to places that evoke feelings of romance, history, endless possibilities: Siena, Orvieto, Todi, Montepulciano, Gubbio, Florence, to name just a few. When I moved here shy of a year ago, I knew I was choosing to create a life in what is a prime tourist magnate. At that time, Covid lockdown was in effect; Americans were shutout of Europe; CNN was featuring Stanley Tucci’s “Searching for Italy,” touting Italian food and culture. In early January 2021, I reached out to my dear friends and family who had been denied visiting me in 2020 in Amsterdam, my official residency, saying we needed to get dates on the calendar for an Italian visit. Within weeks, I also began receiving emails from friends—some closer than others--with proposed travel dates to visit me. The adventurous and optimist ones blocked in travel well before Italy officially opened up in May 2021. My calendar was suddenly crowded. After a year and a half of seeing none of my American friends and family, I was too quick to say yes, not realizing I was signing on from May through November to be a B&B and tour guiding service.
By April, reality set it: I was about to be deluged with company. Most of my visitors would be flying into Rome and picked up by my driver Enzo. A few would arrive by train. They uniformly lacked cars and knowledge of Italian driving regulations (oh, those huge fines for inadvertently driving into a protected historic area). It would be my job to squire them around. I needed a plan. I pulled out my map of Tuscany and Umbria, reached for Frances Mayes’ excellent book, “Always Italy,” and began writing lists of places I wanted to explore as either a day trip or a night or two stay. I would use this time to further acquaint myself with my surroundings.
Guests want to experience Italy from the vantage of being in a private home as much—if not more so —than spending time with you. Yes, of course, they are happy to see you, but they also want to immerse themselves in Tuscany. Pre-planning how you and your visitors will enjoy the prescribed number of days together increases the odds that it is memorable and uplifting for all involved. Entertaining and hosting guests is a job. Prepare yourself by starting with identifying key elements and adjust accordingly:
1. Guests’ physical limitations becomes vital information. Hill towns are notoriously vertical, roads cobbled or uneven. You must walk, climb stairs, and be able to make it from the town’s historic gates to at least the chosen restaurant. How far and steep can your most challenged friend walk before it becomes an ordeal rather than a journey?
2. Dietary restrictions and/or requests need to be known. Having a vegan, gluten or diary intolerant, or vegetarian guest impacts every meal. I had booked coveted seats at Dario Cecchini’s famous restaurant above his butcher shop in Panzano only to discover my guests had recently become vegetarians. Dario’s meat throw down would have repulsed them.
3. What are your guests’ interests? Shopping? Seeing architecture? Art history? Exploring Etruscan civilization? Wineries? One of my guests is a devote Catholic and visiting the Basilica in Cortona that houses Saint Margherita’s remains was very meaningful to her.
4. Daily schedules are a must. Don’t squander precious time trying to figure out what to do. I have a routine on guests’ first day of showcasing Cortona. I begin by walking the Stations of the Cross up to the Basilica (if the guests are physically fit). I love the vast view of the valley across from the University of Georgia, and the ideal setting for offering a sweeping overview of Cortona history, pointing out Lake Trasimene, where Hannibal defeated the Romans in 217 BC, followed with the tale of Saint Margherita and St. Francis. Guests and I enjoy their first meal at La Loggetta, overlooking Cortona’s main piazza, toasting each other with a glass of prosecco before diving into a local Syrah. Afterwards, I take them to DelBrenna to see Megan and Sebastian’s stunning necklaces, and to Andre Roggi’s new gallery featuring his magnificent sculptures. A stop at Molesini Wine Shop is a given, then a stroll down the Via Nazionale, with stops in the cute shops, a gelato to lick along the way.
Andre Roggi's new gallery with La Loggetta restaurant reflected in the windows
5. Figure on two daytrips out of Cortona for a 4 day visit. A few of my favorites are –not in order--*Montepulciano-Pienza, with lunch at the Townhouse in Pienza; *Assisi-Montefalco, with lunch at L’Alchimista; *Arezzo, with lunch at La Lancia d’Oro, followed by a visit to Esselunga to see a major Italian grocery store; *Siena, followed by a drive to Panzano and lunch at Dario Cecchini. I turn this into an overnight trip by booking rooms and dinner at Il Borgo di Vescine; *Deruta-Perugia, with lunch at Osteria a Priori; *lunch and a tour of Antinori’s magnificent new vineyard (must reserve well in advance).
A trattoria in Pienza, Siena
Swimming pool at Il Borgo di Vescine
Tuscan roads, with the a tuscan haze
Inside Antinori vineyard
Grab a ringside seat in a hill town for lunch
Pienza is home to Pecorino and there are many to choose from
6. Do your homework. Make dining reservations well in advance as the good ones are generally full. Map out your road trips with approximate drive times. Parking is a challenge. I downloaded a parking app on my navigation system which has saved me a good deal of stress. Read up on a town before you go and know a few highlights you don’t want to miss. Most of all, allow for some down time to relax and ease into La Dolce Vita. This is your life, too, so take yourself into account during your planning. I have loved this summer and all I have seen, learned, and enjoyed, my guests most of all.
Dear friend Deb, Boo, and me at Pienza's outer wall