Charming stopovers on Tuscan country roads

There’s a heady cocktail of art, history, and wine to be had on this course


Florence is considered the birthplace of the Renaissance. Its galleries and museums alone would keep you occupied for days. Make the time to gape at the ageless Venus by Botticelli (in the Uffizi) or Michelangelo’s David (in the Galleria dell” Academia). The gold market at Ponte Vecchio is a must-visit, if only to see the naked display of bling, and the Duomo is a Florentine icon you cannot afford to skip.


This medieval town is the birthplace of Giacomo Puccini and boasts some of the best architecture in all of Tuscany. The fortification walls around this town double-up as a well-landscaped bicycle and walking path. Lucca’s Duomo and the Church of San Michele are the main attractions, but for a grand view of the city, climb up to the top of the Guingi Tower, or the Torre delle Ore clock tower. Or stroll and shop along the picturesque Via Fillungo.


UNESCO decided to make this sparsely-inhabited gem a World Heritage Site. Surrounded by the gorgeous hiking trails of Val d’Orcia, this little town was rebuilt entirely by Pope Pius II in 1458 to represent the best of Renaissance-era architecture. With just 2,500 inhabitants, this town possesses a quaintly reflective air about it. Zeffirelli filmed the iconic Romeo & Juliet here in 1968, retelling a classic amidst the harmony of its well-planned streets.


This city is most famous for its Palio horse-races in the Il Campo square, held every year in July and August since the 17th century. It was also Florence’s Renaissance-era rival, which would explain its jaw- dropping architecture at every turn of the head, in particular the Duomo, the stunningly-frescoed Palazzo Pubblico, and the gorgeous Pinacoteca with its collection of medieval art. Even today, this city rivals Florence as a base for Tuscan travels.

Crete Senese

A short drive from Siena, situated in the Val d’Orcio, is the classic Tuscan snapshot, the stuff of postcards. Drive through the lunar landscape of Crete and soak in the gorgeous medieval villages and their traditions. Visit the Basilica of St. Agata and the Church of San Bernadino in Asciano, also known for its pecorino (ewe’s milk cheese). Explore San Giovanni d’Asso, a village famous for its black truffle and the rare white truffle.


Apart from being featured in the Twilight series, Volterra remains a quiet, un-touristy town steeped in ancient and medieval Roman history. Its hilltop perch provides gorgeous views of its winding streets and Roman ruins dating back to 1st century BC. Today, the remnants of an ancient defence wall and the main gate to the city still stand, and the amphitheatre and bath-house are a must-see. The Museo Etrusco Guarnacci contains Etruscan artefacts from that time.


This town offers more than just an opportunity to tick the Leaning Tower off your list. Pisa is also known for its Piazza dei Miracoli (Square of Miracles) that houses a gorgeous and ubiquitous Duomo (typical of most Tuscan towns) and the impressive Battistero di San Giovanni. Round off your visit with a shopping spree along the Borgo Stretto, Pisa’s most elegant street, or stroll along the banks of the Arno River, away from the tourist crush.


The name of the region says it all, evoking fruity flavours and aromas of berries among wine lovers worldwide. Its olive oil, pressed in November and December, is a prized ingredient on bruschetta all over Italy. The Wine Festival of Cantine Aperte gives you the opportunity to explore the world of Tuscan wines, but the best tasting is done by visiting individual vineyards. Stay at farm houses (the agriturismi) for the best Chianti-countryside experience.


Chianti may have its fans, but the Vino Nobile di Montepulciano is considered one of Italy’s best, hands down, all the way from the Middle Ages to present date. An ideal itinerary in this town would be to see its lovely churches and quaint architecture in the morning, and spend the rest of the day sipping free wine and sampling the meats and cheeses. Walking around is the best way to see this walled city that dates back to the 14th century.


You may recognise this town by the beautiful backdrop seen in the film Life is Beautiful, and you will understand why. Arezzo has effortlessly retained its pristine charm from ancient times to now. Once a powerful and wealthy town, today it is known for its tranquil charm and being an important hub of art and culture. Visit the Church of San Francesco and feast your eyes on the frescoes of Piero della Francesca, a 15th-century master of the form.