Trails of Tuscany

Arriving in the medieval city of Siena gives the feeling of having stepped back in time. At Siena’s heart is Il Campo; the central piazza and where the Palio horse race takes place twice every summer. After checking in at the hotel, why not head here for a coffee or glass of chilled wine and soak up the Italian ambience and relax into ‘la vita bella’.

On this slow-paced trip there are of course wonderful walks to take in the stunning Tuscan and Umbrian rolling hills, sprawling olive groves and vineyards, but also time to explore the iconic towns at your own pace. You have this afternoon and tomorrow morning free, so we recommend arriving early today to make the most of this first stop in the historical town of Siena.

Siena is a UNESCO World Heritage Site and one of Italy’s must-see attractions. The city is well-known for its wine and cuisine, art, museums, and Gothic architecture. Take time this morning to discover this charming historic town.

Why not add on the "Taste of Siena Food Tour" so you can eat your way through Siena’s hidden corners? Sample tastings of traditional delicacies, local wines, handmade pasta, olive oil and cheese as you walk through the historic centre (tour duration: 3 hrs, 10am start).

This afternoon, take the train (payable locally, approximately 1 hour duration) on a picturesque journey through classic Italian landscapes to Montepulciano. From the train station there is an included transfer to the hotel, where there will be a welcome meeting with our local supplier. The town is known for its red wine ‘Vino Nobile’, so perhaps relax with a glass this evening or purchase a bottle or two to bring home.

This morning starts with an included transfer to Pienza. Pienza is said to boast the most delicious pecorino cheese in the whole of Tuscany—why not stop in at one of the shops and get some to take home? This UNESCO World Heritage town was commissioned by the pope in 1459 to the architect Bernardo Rossellino, with the task of designing the perfect town. Parts of the town were used in the filming of ‘The English Patient’, which was largely set in the nearby Sant’ Anna Monastery. Don’t miss taking a short walk along the wall on the south edge of town to take in the panoramic view.

On the walk back to Montepulciano it’s possible to visit one of the quaint cafes or stop for a picnic lunch in Monticchiello, a stunning hamlet with fortified walls.

Alternatively, instead of joining the walk today, there’s the option of relaxing and exploring the town of Montepulciano. The Church of Sant’Agostino is worth a visit as is the Palazzo Comunale, where it’s possible to climb the tall tower to get a view of the surrounding countryside. The historic Caffe’ Poliziano is an ideal lunch spot. Take a wander around the main square of Piazza Grande and the nearby Fortress of Montepulciano with its delightful gardens.

Ascent/Descent: 522m/464m

Leaving Montepulciano, on a half-day walk through the iconic Tuscan countryside of yellow fields and hilltop villages to Acquaviva. From here a transfer is included to Cortona, where it’s easy to find a quiet spot to relax in the Tuscan sun and read a good book or enjoy watching the world go by.

Alternatively, there is the option to do a longer full-day walk continuing from Acquaviva to Valiano and then transferring from here to Cortona. 

Cortona, located at 600m altitude, is characterised by steep narrow streets and medieval architecture. Pay a visit to the distinguished Etruscan Academy Museum, founded in 1727, or simply enjoy the expansive views from the Piazza Garibaldi.

Montepulciano to Acquaviva: 9km (6 mi). Ascent/Descent: 37m/269m
Acquaviva to Valiano: 7km (4.5mi). Ascent/Descent: 3m/49m
Combined: 16km (10mi). Ascent/Descent: 40m/318m

Cortona is a classic medieval town ideally perched on a hilltop. You may have watched the movie "Under the Tuscan Sun" based on the book by Frances Mayes. Most parts of it were filmed in Cortona and whilst exploring on foot you may recognise various filming locations such as Villa Bramasole, the abandoned Tuscan villa that Diane buys and restores. 

Set off on a short, optional walk along the ancient Strada Basolata Romana to Cortona or spend the day strolling down Via Santa Margherita, browsing the local ceramics shops for unique souvenirs to take home, and admiring big villas set amid sunflower fields and olive groves. There are parts of town that are particularly steep, with narrow streets, but the views will make it more than worthwhile. You can see all the way to Lake Trasimeno in Umbria from Piazza Garibaldi and the Chiana Valley countryside from the city walls.

Cortona is not only a feast for the eyes, have a traditional Tuscan meal and one of its top restaurants followed by a well-earned siesta. 

Ascent/Descent: 397m/406m

After a short transfer from your hotel to Terontola-Cortona train station you will catch a train speeding through photogenic Italian landscapes to Florence’s Santa Maria Novella Station (takes approximately 1 hour 30 minutes, payable locally).

Upon arrival in Florence, known as ‘The Athens of the Middle Ages’, there is then time at leisure to explore this incredible historic city. Immerse yourself in the wonders of Florence there is the option of doing a circular walking loop taking in Florence’s top attractions. Discover Palazzo Vecchio, the infamous fortress, and Florence Town Hall, navigate Accademia Galleria for Michelangelo’s “David,” and be awed by the huge exterior of Florence’s Cathedral “Duomo.”

Ascent/Descent: 113m/113m

According to Lonely Planet, Florence is one of the best cities to travel to in the world, and we couldn't agree more! An extra day here with free time will allow you to explore at your own pace. 

Florence is uniquely compact in size, easy to explore on foot, and packed with art and architecture at every turn. The city has hardly changed since the Renaissance and it should come as no surprise that the entire city centre is a UNESCO World Heritage Site. Its 15th-century palaces, medieval churches, and marble basilicas will keep you reaching for your camera. 

The Tuscan capital is known for its fashion and haute-couture boutiques and walking along its cobbled streets and window shopping is a treat in itself. Florentines share a pride in their culinary traditions; locally sourced, seasonal foods. You will find that one of your challenges is choosing between the huge variety of restaurants and lunch spots today, wishing you could try them all. Life in Florence is sweet, enjoy a slow passeggiata to Ponte Vecchio bridge for views over river Arno or a short walk up to Piazzale Michelangelo to gaze over the skyline of Florence from above. Finish the day off by indulging in an aperitivo at dusk to celebrate the end of a fantastic holiday. 

From Florence it’s easy to take a day trip to Pisa as it is only an hour’s journey between the two cities (please contact us if you would like to add a night here).

Check out of the hotel and continue with onward journey.