Vacation Rentals in ItalyRecently I met Pauline Kenny, who is ‘living the dream’ of traveling for the fun of it. She has written this post today giving us details about vacation rentals in Italy in addition to recommended reading. Please welcome Pauline Kenny, founder of, an online travel community (now owned by Internet Brands, Inc.) Pauline ran the Slow Travel website and community from 2000-2007. She and her husband, Steve Cohen, now run the Slow Europe Website. They have both been traveling extensively for over three decades all over the US and Europe, living in Europe from one to five months every year.

Taking the Time to Experience More of Italy

Lenora’s Italy Retreat for Women is a great way to experience a beautiful part of Italy – the Cinque Terre and the Liguria coast – and the timing is perfect – mid-September when the holiday crowds have returned home and the very hot days have ended. But the week in Liguria will only whet your appetite for Italy; you will want to see more. My favorite regions are close by – Tuscany, Umbria and Le Marche.

From Liguria take the train to Florence, spend a few nights in this Renaissance capital, then pick up a rental car and head out to the countryside. Or pick up a rental car in La Spezia and head out from there. If you have the time, a week in each of these three regions would be a wonderful immersion into Italy. Or pick one region and spend your week there.

If you are flying out of Rome, it is only a couple of hours by car to the airport. Or drop the car off in Chiusi (in Tuscany on the main train line) and take the train to Rome for a visit before you head home. Remember when booking your flight that it is possible to fly into Milan so you arrive close to Liguria, but return from Rome, so you don’t have to drive all the way back to Milan.

If you do not want to rent a car, you can see Tuscany by using Florence as your base. From there you can take trains to Lucca, Pisa, Bologna – even to Rome. Buses will take you to Siena. It is not that easy to get to the small towns, but study the bus schedules and you can do it.

Spoiled for Choice Accommodations

Italy has the full range of accommodation options from luxurious 5-star hotels to family-run inns, from villas for a group of 10 to cottages for two on a farm. My favorite type of accommodations is vacation rentals – houses, cottages or apartments, in cities, towns or the countryside, that you rent by the week (usually Saturday to Saturday). I like to settle into a vacation rentals in Italy, shop in the local village, do some of my own cooking and explore the area from my comfortable base.

Under That Beautiful Tuscan Sun

When I think of Italy, I think of the Tuscan countryside with its curving country roads, hillsides lined with olive trees or grape vines, medieval hill towns and roads lined with cypress trees. Tuscany is mostly rural with mountains in the north and gentle hills and valleys in the rest of the region. The western edge borders the Mediterranean, but Liguria has more interesting seaside towns. The city of Florence (Firenze in Italian) is the art center – Michelangelo’s David and Botticelli’s Venus are my favorites. Siena, south of Florence, has one of Europe’s greatest medieval squares, Piazza del Campo.

My favorite parts of Tuscany are the Chianti, a wine producing area between Florence and Siena, and the Crete Senesi, open countryside dotted with historic hill towns, south of Siena. The main towns in the Chianti are Greve, Panzano, Castelina and Radda, forming a triangle north of Siena. In the Crete the main towns are Montalcino, Pienza and Montepulciano, all close together and all surrounded by beautiful open countryside. You would be happy staying in or near any of these towns.

One of my favorite places in Tuscany is Monte Oliveto, a monastery just north of Pienza, with a magnificent set of Frescoes depicting the Life of St. Benedict painted in the 1400s.

Read more about Tuscany:

Suggested Accommodations: Sant’Antonio ( – vacation rentals on an historic estate near Montepulciano:

Umbria, the Green Heart of Italy

In between Tuscany and Le Marche lies Umbria. While it is not as popular as Tuscany, nor as perfectly groomed, it is full of interesting hill towns and beautiful countryside (endless fields of sunflowers). In Tuscany the art is in the larger towns but in Umbria you find it in the churches in the villages. Assisi can be overrun with Catholic pilgrims, but is well worth the visit, just to see the frescoes in the cathedral.

My favorite area is central Umbria with the towns of Assisi, Spello, Bevagna and Montefalco. In western Umbria, skip the north shore of Lake Trasimeno (boring summer beach towns), but south of the lake are interesting hill towns like Panicale and Paciano. Southern Umbria, with Spoleto and Todi, is also interesting. Any of these areas would be good to stay in.

One of my favorite places in Umbria is the hill town of Spello and the fresco in its church, Pinturicchio’s cycle of the Annunciation, the Nativity and the Dispute with the Doctors. We spent two weeks in Spello and looked at those frescoes every day – I never grew tired of them.

Read more about Umbria:

  • Rebecca’s Blog ( – Rebecca’s life on a farm near Assisi
  • Madonna del Piatto ( – Letizia writes about food and Umbria

Suggested Accommodations:

Le Marche, Mountains and Seaside

Le Marche is less known and less touristed than Tuscany and Umbria, but in many ways is like the Tuscany we experienced traveling there 20 years ago. Less English is spoken, towns cater to locals instead of tourists, restaurants are more “homey”.

Le Marche is mountainous, so prepare yourself for winding mountain roads. It has lovely beaches on the Adriatic. Urbino, in the north, is a magnificent art town. The museum holds the final painting in the “Piero della Francesca Trail”, a series of paintings located in towns in Tuscany and Umbria. Ascoli Piceno, in the south, has a wonderful medieval center.

I must confess that I do not know Le Marche like I do Tuscany and Umbria, so don’t have a favorite spot (yet), but I really liked Urbino.

Read more about Le Marche:

Suggested Accommodations:

Photo Credits: from Pauline Kenny. Top photo: tower, Assisi in Umbria, Italy. Lower Photo of Le Marche – View near Urbino

Have you ever rented in Italy? Do you have a favorite travel destination in Italy? What are your favorite Vacation Rentals in Italy?

Learn more about traveling to Italy on Lenora’s Italy Retreats For Women
Find out more about Lenora’s Sweet Life Workshops and Sweet Life Happiness Coaching.

You are welcome to reprint, copy, or distribute Lenora Boyle’s article, provided author credit is included.