Anyone who has ever driven in Italy will know that it requires a certain degree of patience, fortitude and skill. Travelling by train is recommended. The trains are comfortable, safe, reliable and economical. There are, however, some places where trains are just not practical and this includes some of the most beautiful and picturesque towns in Umbria and Tuscany. In some of these towns you can’t even drive a car into the historic center unless you have a local resident’s permit. Apart from the fact that the streets are too narrow, lots of cars would simply ruin the ambience and beauty of these small villages that date back to Etruscan and Roman times.

Our desire to see some of the smaller towns and villages led us to book an eight-night Country Roads of Umbria and Tuscany tour with Insight Vacations. The Insight coaches are fitted with around 40 seats, fewer than most tour buses, and with just 27 people on our tour, we travelled in style and comfort with way more leg room than any aircraft. With mostly Americans and Canadians in the group, we were the token Australians, other than our tour guide, Ann, a Melbourne girl who had lived in Italy for 20 years and spoke fluent Italian. Her negotiating skills, charm and cultural and historical knowledge ensured that we were very well informed, that everything went smoothly, and everyone’s needs were considered. It’s no easy feat herding a group of 27 camera-snapping tourists but she did it with humour, goodwill and occasional shouts of andiamo (let’s go!)

Church in Lucca Photo by Christine Salins

A church in Lucca, one of the gems of Tuscany.

On each of its tours, Insight offers what it calls Signature Experiences – remarkable experiences that aren’t offered by other companies. For us, that was a visit to the Bramante Staircase in the Vatican on the morning the tour departed from Rome, a privilege open only to Insight and its sister company, Traflagar. The Bramante Staircase is not actually a staircase but rather a graceful spiral walkway designed by Bramante so that the pope could ride to the top of the tower on a donkey. Considering the views of Rome from the top, it wasn’t hard to see why the pope wanted a better vantage point. The experience was combined with a tour of the Vatican Museum and Sistine Chapel, where you’re not allowed to talk even though the artistic splendor renders you speechless anyway.

A stop for lunch at Orvieto, enroute to the Umbrian capital of Perugia, introduced us to Tuscan chef Lorenzo Polegri who demonstrated the simple but skilled art of pasta making in his enigmatically named restaurant, Zeppelin. A great personality, a great lunch and great local wine left everyone smiling. Armed with a signed copy of Lorenzo’s cookbook, we explored the winding, cobblestone streets of Orvieto, which like many towns in Umbria and Tuscany is built high on a hill with commanding views and a long history.

An Insightful Tour of Umbria and Tuscany- Florence Duomo Photo by Christine Salins

Florence is a sophisticated city, rich in history and centuries-old architecture.

If you like chocolate (never trust anyone who doesn’t), then you’ll love Perugia, a vibrant university town with layers of history, good cuisine and Italy’s biggest chocolate festival attracting many thousands of people (all of whom you can trust) every October. It might sound extreme but in Perugia I tried some Absinthe chocolate washed down with a chocolate Porter. There are many reasons to go back to Perugia but I’d go back just for that.

Based in Perugia for three days, we explored the neighbouring towns of Todi, with its fascinating Roman cistern, and Assisi, home of St Francis and one of Italy’s most beautiful cathedrals. Its well-preserved frescos avoided the bombing in World War Two thanks to a German Catholic commander of the occupying force, Colonel Valentin Müller, who also turned a blind eye to Jews hiding there.

In many of the towns Insight visits, it draws on local guides with specialist knowledge – characters with big personalities, like our guide in Perugia and Assisi, Marco, who was animated and engaging with a wry sense of humour. His friends teased him, he said, because his car was a VW Polo.

Umbria is truffle territory and that pungent unique aroma filled many of the glorious food shops specializing in local produce in these small towns. In Spello, it was hard not to go grocery shopping in the wonderful delicatessens but our hunger was satisfied by a five-course meal at restaurant Il Molino, set in what was formerly an olive oil mill and featuring some classic Italian dishes including the local porcini mushrooms.

Spello Photo by Christine Salins

The cobblestone streets of Spello.

Where else would you start a tour of Tuscany but in Cortona, the setting for Francis Mayes’ Under the Tuscan Sun, and close to where Hannibal defeated the Roman army. There is no real connection between these events but there is much more to Cortona, not to mention some trendy cafés and art galleries. In Tuscany, we were based in a hotel just outside San Gimignano for three days with excursions to Siena, Florence, Pisa and Lucca.

While not as big as Florence, Siena has a rivalry with that city going back hundreds of years. According to our guide in Siena – and we think she was only half joking – Florentines definitely cannot be trusted (they obviously don’t eat chocolate). Twice a year, the main square in Siena becomes a race track with thousands of people crammed into the middle while horses race furiously around the perimeter. The square is divided into nine quadrants that signify the districts of the city and are characterized by a different animal. On entering those districts, you can see ceramic tiles on the walls with pictures of the respective animals. Against her parent’s advice, our guide, a caterpillar, entered into an ill-fated marriage with an elephant. People from different districts rarely mix and once an eagle, caterpillar or leopard, it isn’t easy to change your spots. If you have lunch in Siena you simply can’t go past the local specialty, ribollita, a hearty bean soup with crusty bread.

Florence is a sophisticated city, rich in history and centuries-old architecture where a thousand pictures of the Ponte Vecchio are just not enough. It’s also home to the Medici Palace and, of course, Michelangelo’s famous statue of David. Insight’s optional excursion provided fast-tracked entry to see the magnificent David, avoiding the typically long queues. Another optional excursion was to the Machiavelli Villa, not far from San Gimignano, where the prince of politics was banished and spent the last days of his life. Now a winery and restaurant, its Italian barbecue, wine and entertainment made for a very special night.

Leaning Tower of Pisa Photo by Christine Salins

The Leaning Tower of Pisa, a must-see on everyone’s list.

Pisa is not far away and although the tower is on everyone’s list as a must see, I had a leaning for the town itself which is not so crowded with tourists. A bonus was the fact that our visit coincided with the visit of the Italian President and all the pomp and ceremony that accompanied it. It’s also a short trip to Lucca, one of the gems of Tuscany. This is an old walled city with a round, Roman-style central plaza. It is also the birthplace of Puccini and the house where he was born is now a very well set out museum with costumes and original score sheets from his operas. Following a visit to his house you can sit in the sun-drenched square outside the Madame Butterfly Café and enjoy a Campari Spritz while gazing at a statue of the master himself.

There could not be a more memorable finale for a visit to Tuscany than the stunningly beautiful town of San Gimignano with its breathtaking views of the Tuscan countryside. Be there at sunset when the light paints a scene you’ll never forget. San Gimignano is home to Armando e Marcella Pasticceria, selling fabulous pastries and chocolates, and to Dondoli, which has bragging rights as a world champion gelato maker. One of Dondoli’s most popular flavours is Michelle, a delicious confection of saffron, honey, orange peel and almond biscotti created in honour of Michelle Obama prior to her visit.

Venice marked the end of our Insight tour and a return to train travel and sorting out our own schedules and arrangements. Our tour director, Ann, had reminded everyone at the start that Italy could be complicated and difficult but that you just had to accept it and go with the flow. With Insight taking care of all the arrangements, it was certainly easier to sit back and enjoy watching the landscape of these beautiful regions unfold.

Ponte Vecchio Photo by Christine Salins

Ponte Vecchio, Florence.

If you go

Insight Vacations offers luxury coach tours in Britain & Ireland, USA & Canada, North Africa & Eastern Mediterranean, Europe, India & Asia.

For more Tuscany, read:
Treasures of Tuscany: Truffles to Tiramisu