ITINERARY - 12 nights

Fly to Florence [2] > Start Bike Tour - San Donato [2] >Arezzo [1] > Cortona [2] > Rent a car and drive to San Giovanni D’asso [5] > Rome

For the first time Michael and I joined an organized bike tour in Tuscany. I was hesitant at first since I’m not keen on traveling with a large group, but Michael’s dad Harry wanted to do this for his birthday and we thought we would give it a try. It ended up being a very nice experience. But the best part was that after the tour, we rented a small villa in a different part of Tuscany and coincidently one of the guides on the tour, Alessandro, lived in the area and offered to take us riding. We also had dear friends who live in Padova, join us for a few days. It turned out to be a spectacular trip!

Bike Tour:

Days 1 & 2: San Donato

Zig zag ride through olive groves and amidst stone villas. Visit the Medici estate and olive press. STAY Fattoria Degli Usignoli [farm hotel build in the 1400s]

Day 3: Arezzo

During today's ride we stopped at the hill town of Lucignano - a medieval village with a typical concentric rings structure - a real gem! At the end of the day wet climbed up to the Renaissance gem of Arezzo, home of Piero della Francesca’s work. Arezzo is not as popular on Tuscany’s touristic itinerary so it has less visitors and lot more locals. STAY Vogue Hotel Arezzo

Days 4 & 5: Cortona

At the end of today’s ride, we climb to the top of the exquisite hilltown of Cortona. And what a climb this was!! Cortona is a very charming town even if a bit touristic, with Roman arches, Etruscan tombs and Renaissance palaces.

On day 5 we do a day ride to Lake Trasimeno through wheat and sunflower fields and several small villages. STAY Villa Marsili [restored villa with beautiful views of the valley below]

San Giovanni D’Asso small town in Tuscany famous for it’s truffles, specially the sought after and costly white truffles. With a population of just 853, the town itself does not have much to be seen, except for its splendid setting and the Museo del Tartufo (truffle museum) inside the castle. Every November a truffle festival is hosted in San Giovanni D’Asso, making it a destination if only for two weekends. We really liked how quiet and very well located this town is for exploring the area. STAY Villa La Capanna [located in the heart of San Giovanni d'Asso in the upper part of the village - the "Borghetto", near the ancient castle] EAT La Locanda del Castello [located just across the street from the villa at the base of the castle, the white truffle risotto is not to be missed!] Taverna da Roberto in Montisi, another small and very charming village nearby.

Towns to be visited in the Val D’Orcia area: Siena [a lovely medieval city and worth visiting, bit know it is quite popular with tourist. Siena's heart is its central piazza known as Il Campo, which is known worldwide for the famous Palio run, a horse race around the piazza every summer. We did not get to see it but enjoyed walking around and eating a lovely gelato] Pienza [one of my favorite towns in the Val d’Orcia. It is a UNESCO World Heritage Site and suberb example of Renaissance architecture. We were lucky to visit Pienza during the Infiorata festival when flower petals are used to create both simple and elaborate designs of flower carpets along the streets that lead up to church. The Infiorata’s crowning moment is when the Corpus Domini procession passes down the centre of the carpet of flowers] Montalcino [a classic Tuscan hilltop town, set within a full circle of fortified walls and watched over by a medieval castle; also famous for its Brunello di Montalcino red wine. A picturesque town to walk around and do some wine tasting] Montepulciano [the highest hilltown in Tuscany, boasts vast panoramas all over the wonderful Val D'Orcia. It is full of elegant Renaissance palaces, ancient churches & charming squares like most of the towns we visited in the area] Bagno Vignoni [a popular village well known for its hot springs]

Two abbeys worth visiting: Abbazia di Monte Oliveto Maggiore [a large Benedictine monastery not far from Asciano situated in a forest of cypresses and oaks] Abbey of Sant'Antimo [a former Benedictine monastery with a beautiful Romanesque church, in a picture-perfect setting near Montalcino. It sits in a large valley with views of rolling hills covered in olive groves and vineyards]