Tuscan Wanderlust

Head off the beaten path where ancient routes link Etruscan Cortona with Montepulciano and Pienza. Explore picture-perfect hilltop towns and ancient abbeys. Each day’s leisurely pace is interspersed with samplings of ribollita and pappa al pomodoro as well as conversations with the locals.

Day 1 – Cortona
Gather in Cortona, and begin an afternoon guided tour through the Etruscan-Roman village. We'll check out the four well-preserved city gates and embark on our first climb into the hills, to view Renaissance churches. Then we head over to visit an Etruscan tomb, and follow an ancient wall.

Day 2 – Pienza
Shuttle to Montepulciano and take a leisurely hike into the 15th-c. Renaissance town of Pienza. Most of the major buildings here were constructed by Bernardo Rossellino, a famous Renaissance architect. On the way, we'll pass through the phenomenal "Crete" landscapes (barren, eroded gullies). This evening enjoy an Italian lesson before our delicious meal at a local trattoria.

Day 3 – Bagno Vignoni
Hike through forested areas and colorful fields to S. Quirico D'Orcia. Here we'll stroll through the main street to admire Romanesque carving on early pilgrimage churches. Explore the Tower of Vignoni Alto before winding down to the spa town of Bagno Vignoni.

Day 4-5 – Montalcino
Shuttle to Ripa d’Orcia, a riverside castle-hamlet. We then hike through a valley and across a river to the Etruscan walled village of Montalcino. This town is home to Brunello, one of Italy’s most prestigious red wines, and our winetasting session this evening will show you why! On day 5, we loop to Monte Oliveto Maggiore for a two hour walk through a gorgeous landscape and small villages. In the evening, attend a private cooking lesson for first-hand instruction on preparing local specialties, followed by a delicious Tuscan feast.

Day 6 – Arrivederci!
Shuttle to Siena’s train station for late morning goodbyes. Why not extend your journey with a few extra days in Siena or a visit to Florence? We are happy to assist you with any further travel plans.