Trails of Tuscany

Day 1: Arrive Montepulciano

We will meet as a group in Florence, then travel by train to the beautiful hill town of Montepulciano, the largest in Southern Tuscany, in the afternoon. Once you arrive at our hotel in the heart of the city, we will meet and greet with our fellow adventurers orienting everyone for the week. Look forward to heading out on the town with new friends for a traditional Italian feast!

Day 2: Montepulciano

With its beautiful Renaissance buildings, duomo (cathedral) housing 15th century art, and breathtaking views, Montepulciano is just the place to recharge your batteries after a long day of travel. We'll gather as a group in the morning for sharing and reflection. Then it’s a day to explore or shop. The impressive Piazza Grande and its whimsical bell tower crown the town with cafes and a wine tasting shop. There you can taste wines from the world famous Vino Nobile region or explore boutiques among the cobblestone streets.

Day 3: Pienza

Today is our first day of hiking! Our destination, Pienza, is often referred to as "The Pearl of the Renaissance" with its almost perfectly intact town center, the palace of Pope Pio II, Bishop's Palace, and Town Hall. Once we arrive at our beautiful hotel we'll kick off our shoes and enjoy everything our hosts Nikola and his family have to offer!

Days 4-5: Bagno Vignoni

Bagno Vignoni has been famous since Roman times for the sulfurous waters that come bubbling up into the large rectangular pool that forms the town's main square, Piazza delle Sorgenti (Square of the Springs). Medieval pilgrims and modern hikers alike have soothed their tired feet in the pleasantly warm water that flows through open channels on its way to the River Orcia. Of particular interest are the ruins of a medieval bathhouse on the edge of town and the Chapel of Saint Catherine. After our hike to Bagno Vignoni we'll be staying in what was once Pope Pio II Piccolomini's summer residence, which overlooks the town's main square.

On our day of relaxation and pampering indulge in a massage, rejuvenate in the magical waters, or stroll along the Orcia river and explore the area. On this evening we are treated as guests in the home of a local family who will teach us the art of Tuscan cooking and spoil us with a feast.

Day 6: Montalcino

In the morning we will walk from Bagno Vignoni to San Quirico D’Orcia, and then travel to Montalcino. Perhaps known best for its Brunello di Montalcino wine, Montalcino has a rich history of art and architecture. There you will be able to soak up the glorious art at the Musei Riuniti, see the medieval fortress in town, or indulge in a wine tasting. In the late afternoon, under pastel skies, we’ll gather on the patio of our boutique hotel for sharing and celebration.

Days 7-9: Siena

After breakfast we will walk out of Montalcino toward Siena on our final day of hiking. Siena, with its shell-shaped center, Piazza del Campo, has been declared a UNESCO World Heritage Site. The square is home to a number of architectural treasures and a semi-annual horserace. The Duomo di Siena is one of the greatest examples of Italian Romanesque-Gothic Architecture. Hundreds of thousands of people flock to the city each year to see the art and architecture of this jewel of the renaissance.

Spend the day exploring this medieval city, shopping in its local boutiques and chic fashion shops or just enjoying a caffe on the Piazza del Campo. When evening comes we'll indulge in our final feast together and celebrate our week's accomplishments!

Our final breakfast together will leave us with full bellies and full hearts. Take the morning and afternoon for last - minute shopping , cappuccinos, sight-seeing, and good-byes before your departure to the airport or your next destination.