Day One - Sunday, September 14

Arrival Day - Florence - San Gimignano; 4 miles, easy with elevation gain of 150 ft

• Meet in central Florence and depart on foot, ascending a lovely lane to the church of San Miniato al Monte, which commands a stunning view over the city and the Arno River Valley. Your route follows Via San Leonardo, meandering past elegant private villas and gardens to the hilltop village of Pian de’ Giullari, or “field of minstrels,” where Galileo lived and worked in the 17th century.
• Stop for lunch at a quaint local restaurant, overlooking the enchanting landscape.
• Bucolic country paths bring you to your final destination, one of Tuscany’s finest Romanesque basilicas and one of the most beautiful churches in Italy. Built in 1013 by Bishop Hildebrand, San Miniato holds exquisite artwork by some of the most revered Renaissance masters. After visiting the church, transfer to the striking town of San Gimignano.
• Upon arrival, enjoy an introductory walk of this historic town. As you stroll the alleyways, you will learn about the importance of the “town of the lovely towers” in the Middle Ages and its cathedral, which is home to one of the most beautiful cycles of 13th and 14th century frescoes; perhaps even walking to the town’s fortress for a bird’s-eye view of the towers.
• This evening, enjoy a welcome cocktail before feasting on regional specialties at your charming town hotel.
• Overnight at Hotel La Cisterna in San Gimiginano.

Day Two - Monday, September 15

Villa Pignano - Volterra; 6 miles, easy to moderate.

• After breakfast, you have a short bus transfer to the start of your scenic stroll through a classic Tuscan landscape. Today’s itinerary offers sweeping views of distant hills as you walk a country lane between the tiny hamlet of Pignano and the walled, hill-top town of Volterra. The undulating walk crosses an exhilarating, open landscape toward Volterra. In this Etruscan, Roman, and medieval town, begin your visit with the Etruscan walls and tombs — continue in history to the Roman baths and theater. Finally, enjoy a stroll along medieval streets, all while glimpsing at romantic gardens. Time permitting, you may visit Volterra’s excellent Etruscan museum.
• Following some independent time for strolling and lunch, return to San Gimignano in the late afternoon. There is time to refresh before you walk to town for dinner at a cozy restaurant that specializes in traditional Tuscan cuisine.
• Overnight at Hotel La Cisterna in San Gimiginano.

Day Three - Tuesday, September 16

San Gimignano - San Donato - Ruins of Castelvecchio; 6 miles, easy to moderate with an elevation gain of 600 ft; 6 miles, more challenging afternoon option.

• This morning, leave San Gimignano on foot, following a road that provides wonderful views of the town’s spectacular towers. The imposing and lofty skyline gives you an appreciation of the effect the sight must have had on medieval pilgrims.
• Walk through a rolling countryside of olive trees and grape vines and continue to the hamlet of San Donato to enjoy a farmhouse lunch alfresco. The farm is a family-run business that produces its own Vernaccia and Chianti wines and olive oil.
• After lunch, you may return to San Gimignano to browse shops, visit museums, or climb the highest tower! For those who would like to participate in the afternoon walk, the hearty meal fuels you for your visit to Castelvecchio, one of the last places in Tuscany to be hit by the Black Death of 1348. This terrifying outbreak of the bubonic plague took approximately two out of every three lives in Europe. When word reached neighboring towns that Castelvecchio had been infected, troops were sent to surround the village so that no one would enter or leave. After a few months, when the inhabitants were believed dead, a reconnaissance patrol discovered that the town was empty. The villagers had apparently fled by a secret passage. The town was never inhabited again but today we are able to explore the vine-covered ruins.
• This evening you are free for dinner on your own: at a simple pizzeria, a bustling trattoria, or an elegant restaurant in the pedestrian center of San Gimignano.
• Overnight at Hotel La Cisterna in San Gimiginano.

Day Four - Wednesday, September 17

Castel Petraia - Monteriggioni - Radda in Chianti; 5-6 miles, easy to moderate.

• You will begin your day with a short drive through the rolling countryside to the medieval fortress of Castel Petraia, a fortified manor at the foot of Monte Maggio, whose wooded slopes separate the valley of the river Elsa from Siena and its plain. It is an area of geological interest due to limestone with a preponderance of holes and bubbles producing many deep natural caves. Here a peaceful two-hour walk loops around the foot of the mountain through Mediterranean macchia (shrub) and fields of iron-rich red soil (from which the pigment known as raw Siena is drawn), to the castle of Monteriggioni. This imposing, circular fortress, likened by Dante to a stone crown upon its hill, was built by the Sienese to guard the border with Florence. Ascend a very steep, but short (10- minute) walk into the castle, where you are rewarded with the opportunity to browse the village shops, such as a fine erboristoria (herb shop), sip a cappuccino in the main square, or enjoy a casual panino (sandwich) lunch in one of the town’s cafés.
• After lunch, drive approximately one hour to your next home in the town of Radda in Chianti, once a Florentine fortress and the capital of the Chianti League in the 14th century. Situated on a ridge 1700 feet above sea level, Radda has maintained its medieval elliptical shape with ancient streets radiating from the historic Piazza Ferrucci and its stately 15th-century town hall.
• Your hotel for the next three nights combines the feel of a country villa with the convenience of an in-town hotel, thanks to its pool, spacious grounds and views.
• Before dinner at a wonderful restaurant in town, you may choose to relax by the pool or sip an aperitivo in the garden.
• Overnight at Relais Fattoria Vignale in Radda in Chianti.

Day Five - Thursday, September 18

Panzano in Chianti - Volpaia - Siena; 5 miles, easy to moderate.

• After breakfast, a short bus transfer takes you to the starting point of your walk, midway between Florence and Siena. Your walk begins at a point located between the Val di Greve and the Val di Pesa, and takes you down a quintessential country road dotted with vineyards, olive trees, and farmhouses. Sheep and goats can also be found grazing; their milk used for local specialty cheeses.
• Soon you see your final destination in the distance — the fortified, hillside hamlet of Volpaia. One of the best preserved villages of its period, the castle was built in the 11th century. Upon arrival, you have some time to stroll picturesque lanes and alleys, yet lunch awaits you in a lively country restaurant with homemade soups and fresh pastas.
• After lunch return to your hotel to rest and prepare for your afternoon exploration. Crucial to understand the art and history of Tuscany, this afternoon visit the hill-top city of Siena. Your special guest lecturer provides a fascinating introduction to the city’s history and art. The guided tour begins in the heart of Siena, the Piazza del Campo (main square) with its impressive town hall, or Palazzo Pubblico. The main square is also the setting of the celebrated Palio horse race. Wind through the pedestrian streets making your way to the 13th century Duomo (cathedral) with its striking black-and-white- striped marble facade.
• Following your group tour, this magical city is yours to enjoy for the evening. Whether you prefer shopping or strolling, you will surely culminate the evening by dining on classic Tuscan delights; choices range from wild boar and risotto to simple, authentic pizza!
• Overnight at Relais Fattoria Vignale in Radda in Chianti.

Day Six - Friday, September 19

Radda in Chianti - San Donato in Perano; 6.5 miles, easy to moderate. Fattoria di Vistarenni; 2 miles, easy to moderate afternoon option.

• After breakfas depart from your hotel on foot through the heart of the Chianti Classico wine-producing region. Your walk begins on a country road where you pass picturesque, working farms as well as luxurious, private villas with landscaped gardens. Panoramic views of vineyards and olive trees provide an understanding of the landscape, shaped since Etruscan and Roman times.
• Skirting a vineyard, your walk takes you to the charming, fortified hamlet of Vertine, which once belonged to the noble, Florentine Ricasoli family. You soon arrive at the recently restored 11th century estate of San Donato in Perano, just in time for a delightful lunch. The estate produces its own wine, olive oil, and local gastronomic specialties.
• An optional walk after lunch leads you through a cypress-lined lane to the 18th century noble villa of Vistarenni.
• This evening enjoy a festive farewell dinner at a former monastery known as Badia a Coltibuono, near the town of Gaiole in Chianti. Founded in 1051, the monastery was once owned by the Vallumbrosan order of Benedictine monks. Today the privately owned farmhouse villa produces its own wine and other agricultural products, features a well-known restaurant, and maintains graceful, manicured grounds and gardens. Time permitting, visit gardens of aromatic herbs and lemons before tasting regional wines.
• Overnight at Relais Fattoria Vignale in Radda in Chianti.

Day Seven - Saturday, September 20

Depature.

• After breakfast, you are escorted to Florence where you big your group farewell, reflecting on the spirit of Tuscany.
• For those continuing to the Cooking itinerary, transfer to Figline Valdarno.

Day One - Saturday, September 20

Arrival - Welcome dinner.

• Transfer at a pre-arranged time from Florence to Figline Valdarno, set in the triangle formed by the great cities of Florence, Arezzo and Siena. Your home will be Hotel Villa Casagrande, a palazzo built in the 13th century by a very influential Florentine. Over the years the villa has been a gathering place for artists and philosophers. It has offered hospitality to great leaders such as Pope Leo X, King Charles VII of Bourbon, King Charles V of Spain, and more recently Prince Umberto of Savoy and his wife, Princess Maria Jose. Today it is a comfortable hotel blending history and modern comforts.
• For those transfering from the Country Walkers program, arrival in the early afternoon and time to explore the town and grab lunch on your own. Perhaps enjoy some time at the Villa Casagrande's newly opened spa.
• This evening, a welcome dinner at Chef Claudio’s restaurant, the Ristorante Torre Guelfa.

Day Two - Sunday, September 21

Cooking class - Chianti Classico - Montagliari.

• Breakfast and transfer to Chef Claudio’s country B&B for a cooking lesson in his teaching kitchen. You will prepare many dishes, including appetizers, first and second courses, and dessert.
• Lunch to follow based on your efforts.
• In the afternoon, depart with your English speaking guide for a half-day excursion to the famous Chianti Classico region. Your first stop is Greve in Chianti, where you will have some time to explore this charming village with its covered archways, visit the famous butcher shop Falorni, and have a tasting in a local, “high-tech” wine cooperative.
• Afterwards it is on to the nearby castle village of Montefioralle, with a spectacular view of the valley, a great “photo op.”
• Before dinner at a delightful farmhouse restaurant, Fattoria di Montagliari, you will have the chance to walk through the cellars; the farm produces their own Chianti Classico, a sweet Tuscan dessert wine (vin santo), and a small production of balsamic vinegar (mosto di chianti).
• Enjoy a Tuscan dinner at Montagliari and transfer back to Figline Valdarno.

Day Three - Monday, September 22

Arezzo - Cooking class.

• Breakfast and transfer to Arezzo, a city rich in ancient, medieval and Renaissance history. The Renaissance architect and artist Vasari hails from this town, and the famous frescoes of Piero della Francesca can be found in the church of San Francesco.
• Enjoy a two-hour guided tour through the historical center and picturesque alleys where the Oscar-winning film “Life Is Beautiful” was filmed. Your visit of this beautiful but lesser-known Tuscany jewel will be led by a licensed guide who also took part in the restoration of the Piero della Francesca frescoes.
• Lunch on your own in Arezzo.
• Return to Figline Valdarno for an afternoon cooking class with Chef Claudio.
• Farewell dinner to follow, based on your efforts.

Day Four - Tuesday, September 23

Departure.

• Breafkast, and group transfer to Florence.

Included in the Country Walkers program:

• Three nights accommodation in San Gimignano at La Cisterna Hotel
• Three nights accommodation in Radda in Chianti at Relais Fattoria Vignale
• Daily breakfast
• Guided walking tours as per itinerary
• Four dinners and five lunches (water and soft drinks included)
• Transportation and luggage porterage

Included in The International Kitchen program:

• Three nights accommodation in Figline Valdarno at Hotel Villa Casagrande, double occupancy
• Daily breakfast
• Two hands-on cooking classes with Chef Claudio, meal to follow
• Welcome drink with visit of the Villa Casagrande
• Welcome dinner at Chef Claudio’s Ristorante Torre Guelfa
• Half-day excursion to Chianti (tasting not included)
• Dinner at Fattoria di Montagliari
• Excursion to Arezzo with two-hour guided tour with licensed guide
• Wine with all included meals
• Roundtrip group transfer from Florence