Tuscany, home to famous artwork, superb cuisine, and impressive medieval towns, is widely regarded as one of the loveliest regions in Italy and a wonderful place to explore on foot. Hiking through a timeless landscape along paths that wind through vineyards and past ancient farmhouses, shopping for locally produced specialties, relaxing in romantic outdoor cafes, or exploring the art and architecture of the well known towns of Florence and Siena, Tuscany is truly a feast for all the senses.

May 17– Meet in Rome If your flight arrives in the morning, you can choose to join your guide seeing some of Rome’s famous sights or explore on your own. Regardless of when you get here, we’ll meet at our hotel in Rome in late afternoon to start getting acquainted before going out for our first dinner together. We’ll have an early evening so that those of us with jet lag can get to bed early. Overnight Hotel San Giusto in Rome (D).

May 18- Rome/Montepulciano Today we will leave Rome on a mid-morning train and head to Chiusi through the beautiful Tuscan countryside. We will meet our Italian guide in Chiusi where we will take a short shuttle to the town of Acquaviva. From there we'll hike through the hilly countryside (approximately three hours) to the ancient walled city of Montepulciano, a medieval and renaissance hill town of exceptional beauty. Upon arrival we will check into our hotel, Hotel Marzocco. The rest of your afternoon can be spent visiting the sights of Montepulciano, perhaps taking a short hike to the 16th century Sanctuary of the Madonna of St. Blaise just outside the city wall. Also appealing are the wonderful shops and wineries located in the city or simply relaxing in the town center or in your hotel room. Dinner tonight will be at our hotel, Hotel Marzocco. (B, D)

May 19 - Montepulciano/Pienza (about 5 hrs walking time) Today we hike to Pienza. A dirt road takes us from the San Biagio church on the outskirts of town to Montichiello, a charming village immersed in the "Crete" (Crete meaning Clay). The vistas along the way are the archetypal Tuscan landscape, with rolling hills crowned by cypress trees. We will work up our appetite as we turn steeply uphill to reach the town and a wonderful café for lunch with a magnificent view. After lunch we will continue our hike to the town of Pienza. Pienza, rebuilt in 1462 from a village called Corsignan, was intended to be an ideal Renaissance town. It represented the first application of urban planning concepts, creating an impetus for planning that was adopted in other Italian towns and cities and then eventually spread to other European centers. We will have an opportunity to visit the town, which is also well known for pecorino cheese and truffle production. Our hotel that night is Hotel Corsignano in the center of Pienza. (B, L, D)

May 20 - Pienza/San Quirico d'Orcia/Bagno Vignoni (about 5 hours walking time) As we leave Pienza we walk down from the town with a view of the rolling Tuscan landscape always before us. 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 cafés 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. (B, L, D)

May 21 - Bagno Vignoni/Sant'Antimo/Montalcino (about 6 hours walking time)– This is our longest day, starting with a tough uphill (now you know why the towns are called Tuscan Hilltowns). After achieving the high point of our day we are rewarded with the descent. The descent towards the Orcia river is shaded and a rather untouched environment. 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 picturesque spot 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 ice cream or cold beverages to refresh us from our hike. There will be ample time to explore the Abbey grounds and enjoy the beauty of the interior of the Abbey before being driven to Montalcino. Our hotel tonight, Hotel il Giglio, is situated in the center of Montalcino and serves a wonderful dinner. (B, L, D)

May 22 – Transfer to Mount Oliveto Maggiore (about 3 hours walking time)- The Monte Oliveto Maggiore, an imposing brick building in a rugged landscape, is the mother house of the Olivetians, or White Benedictines, a congregation of monks founded in 1313 by Blessed Bernardo Tolomei of Siena. The abbey's hours are usually morning and evening with a midday closure, so we'll be shuttled from our hotel in Montalcino to the Abbey in the morning. We'll visit the beautiful cloister with Signorelli’s frescoes before we start our hike to Pieve a Salti, a farmhouse where we can enjoy a cool drink. We then transfer to our agriturismo, Fattoria del Colle in Trequanda. We'll have some personal time before dinner. Known for its wines and its olive oils, this agriturismo is the perfect place to relax. (B, D)

May 23 - Today we’ll give our legs rest as we enjoy a non hiking day and a visit to Siena, the best preserved great medieval city in Europe. Fattoria del colle is a wine producing farm and in the morning we take a nice walk in the vineyards, ending with a visit to the winery and a wine-tasting with a light lunch. In the afternoon we transfer to Siena and have a tour of town, visiting the Duomo and Piazza del campo where we will enjoy an ice cream looking at the tourist crowd. After some free time for shopping, we end the day at Poggio Alloro, an organic farmhouse facing the San Gimignano towers. (B, L, D)

May 24 – Hiking from Colle di Vald’Elsa to San Gimignano. We start our hike today in Colle Val d’Elsa, where the fascinating old town occupies the crest of a ridge high above the valley of the Elsa. This is a pleasant rolling hike which ends in San Gimignano, a lovely little town with lots of interesting shops, friendly people, and fabulous gelato. You will have ample time to explore all the wonderful things that the town has to offer before returning to Poggio Alloro for a cooking class with Cristina and Alfonsa. (B, D)

May 25– We’ll explore the Chianti countryside today as we hike from Panzano to Volpaia castle, a tiny hamlet with a famous winery. We'll have lunch and then transfer back to the Fattoria Valle, a lovely and welcoming manor house just outside the charming town of Panzano. (B, L, D)

May 26- Today we transfer to the well known city of Firenze (Florence), birthplace of the Renaissance. There is more to see here than can be seen in one day! Your guide will make sure you know where the most famous sights are. That night we’ll gather for a final farewell dinner as we say goodbye to this beautiful area and each other. Overnight at Hotel Goldoni, an antique palace in the heart of the historical area of Firenze (B, D)

May 27- The trip officially ends this morning. You may choose to continue your Italian vacation or, if you must, fly home from the Florence airport. (B)