Meet in Rome at 5 pm. If your flight arrives in the morning, Rome is an easy place to find your way around and there are many sites to visit after dropping your luggage off. We will be spending that night at the Papavista Relais, a charming B&B within a 5 minute walk of the Vatican Museums. Regardless of when you get here, we meet at our lodging in Rome in late afternoon to start getting acquainted before going out for our first dinner together. While we plan an early evening so that those of us with jet lag can get to bed early, undoubtedly some of will go in search of our first creamy taste of gelato. Overnight in Rome (D)

Rome to Montepulciano. Today we will leave Rome on a morning train and head to Chiusi through the beautiful Tuscan countryside. We will meet our Italian guide in Chiusi for a shuttle to the ancient walled city of Montepulciano, a medieval and renaissance hill town of exceptional beauty. After dropping our luggage off at our lovely villa just outside of town we will have lunch at an historic winery were we will get to sample Nobile de Montepulciano, one of the regions famous wines. After lunch there will be free time to explore the town before heading back to our villa. Overnight in Montepulciano at a lovely Tuscan villa. (B, L, D)

Pienza/San Quirico d'Orcia/Bagno Vignoni. The day starts with a short transfer to the town of Pienza. Pienza is the agricultural center of pecorino cheese and truffle production. We will have time to explore before walking out of town. The hiking today is across a beautiful region of rolling hills, oak woods, and quiet, pleasant villages. It ends in Bagno Vignoni, where we find both ancient and modern natural Roman thermal bathing pools. Once arriving in the village you are free to explore, sit in outside cafes and sample their wines, or indulge yourself with a dip in a private thermal bathing pool. Our hotel tonight is a wonderful family owned hotel, Albergo Le Terme in Bagno Vignoni. Walking time - 5 hours (B, D)

Bagno Vignoni/Sant'Antimo/Montalcino. This is our longest day, starting with a tough uphill (now you know why the towns are called Tuscan hill towns). After achieving the high point of our day we descent towards the Orcia river. Our path is shaded and we will be walk through beautiful untouched areas. It leads us to St. Antimo, a lovely abbey isolated in the middle of a pastoral landscape surrounded by grazing herds that add to the serenity of the scene. This Abbey can be seen long before arriving and gives us a feeling of peacefulness before even setting foot on the grounds. On our way there will be an opportunity to sample local gelato or cold beverages to refresh us from our hike. After exploring the Abbey we will met our van who will take us to the town of Montalcino. We will have a an aperitif before dinner at an an "Enoteca" (wine cellar) with a superb view. Our hotel, Hotel Dei Capitani, over looks the Valleys of d'Orcia and d'Arbia. Walking time - 5 hours (B, D)

Montalcino/Pieve a Salti. We will leave Montalcino and hike amongs the Brunello vineyards and stop at a winery which employs only women. We will visit, taste their delicous wines and have lunch. We will continue to Crete Senesi, Senesi, "Siennese clays," which gives the soil a distinctive grey colour and the landscape an appearance often described as lunar. This characteristic clay, known as mattaione, represents the sediments of the Pliocene sea which covered the area between 2.5 and 4.5 million years ago. From Montalcino the path takes us through some famous local wine estates and scenic meadows for sheep farming, and plots of land for crops like corn, tobacco, wheat and barley. Overnight at Pieve a Salti, a beautiful farmhouse. This agriturismo, known for its pastas and its olive oils, is the perfect place to relax. Walking time - 5 hours (B, L, D)

Pieve a Salti/Monte Oliveto Maggiore/Pieve a Salti - We will begin with a transfer to Monte Oliveto Maggiore, an imposing brick building in a rugged landscape. It is the mother house of the Olivetians, or White Benedictines, a congregation of monks founded in 1313 by Blessed Bernardo Tolomei of Siena. We will visit the closter with Signorelli's frescoes in the morning before the crowds arrive before we hike back to Pieve a Salti. We will have lunch at an 'Alimentari' (a small food shop similar to a deli) in the tiny village of Chiusure before returning to the agriturismo. We will arrive in time to relax and perhaps take a dip in the pool. Walking time - 3 hours (B, L, D)

Siena - Today we will transfer to the trail head where we will hike into famous Siena. Siena, the best-preserved medieval city in Europe. After lunch on our own we met back in Piazza del Campo, where the "Palio" is run. We will visit Siena Duomo, the medieval cathedral built between 1215 and 1263. Our last stop for the day will be for gelato before transferring to our Agriturismo in San Gimignano. Walking time - 4 hours (B, D)

Today we will transfer to Colle di Val D'Elsa and hike back to San Gimignano. The trail is lovely and goes through vineyards with stunning views along the way of the San Gimignano towers. We will have time to visit and explore San Gimignano before returning to our Agriturismo. (B, D)

Today we will explore the Chianti region. We start in Greve to walk to Panzano. Greve is a quaint town known for it's town square which is known for its unusual shape. We will walk to Panzano another lovely village. We will have lunch at a local butcher and learn about this local business. After lunch we will return to Fattoria Valle where we’ll have a cooking course and enjoy our efforts for dinner. (B, L, D)

Today we head to Firenza (Florence) birthplace of the Renaissance. There is more to see here than can be done in one day but we will explore the highlights with a guided tour where we will learn some of the famous cities history and see the cultural wonders. Tonight, we will enjoy our last Italian feast together. (B, D)

Sadly our exploration of Tuscany has to end. You are free to leave anytime today. (B)