DAY 1

You meet in central Florence and depart on foot, ascending a shaded lane to the church of San Miniato al Monte, which commands a stunning view over the city and the Arno Valley. The route follows Via San Leonardo, meandering past elegant private villas and gardens to the hilltop village of Pian dei Giullari, or “field of minstrels,” where Galileo lived and worked in the 17th century. You stop for lunch at a quaint local restaurant, overlooking the enchanting landscape. Bucolic country paths bring you to your final destination, the Piazzale Michelangelo, a breathtaking panorama balcony hanging above Florence, where presiding over the piazzale, or square, is the basilica of San Miniato al Monte. Jewel-like and built between the 11th and 13th centuries, its green and white marble façade is one of the finest examples of the Florentine Romanesque style. It also houses fine artworks by Michelozzo, Luca della Robbia, and the splendid frescoes by Spinello Aretino.

Concluding the day’s walk, an approximate one-hour drive takes you to San Gimignano, the tower-topped medieval town in the heart of rolling countryside. Upon arrival you enjoy an introductory walk of this historic town. As you stroll the alleyways you 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. You move on to the town’s fortress for a bird’s-eye view of the towers.

After checking into your charming in-town hotel and refreshing, you gather for an aperitivo in the town center. This before-dinner drink whets your appetite for a feast of local cuisine, with views from your hotel’s dining room over the Val d’Elsa valley.
Hotel La Cisterna, San Gimignano

DAY 2

After breakfast at your hotel, a short drive takes you to the start of a scenic ramble through classic Tuscan landscape—from the tiny hamlet of Pignano you set off on a country lane through open fields and an undulating landscape toward Volterra with views of distant hills. In the walled, hilltop town of Volterra you can choose how you would like to explore its narrow fossil-embedded cobblestoned streets. With a quick overview from your guides, you can be free to stroll and browse on your own. Or, if you wish to remain with your guides, they provide a walking tour of the city explaining its history, art, and architecture, which encompass both Etruscan ruins and a Roman bath and theater. The Etruscan Museum provides further insight into the pre-Roman inhabitants of the region. Volterra is also famous for its high quality alabaster and in one of its small alabaster workshops you can watch artists at work. For either option, lunch is on your own. You gather again in the late afternoon for your ride back to San Gimignano.

Later, you walk to a traditional Tuscan dinner at a cozy trattoria in town. Choose from an array of authentic, homemade dishes including such Tuscan favorites as cinghiale in umido (stewed wild boar), tagliatelle con funghi porcini freschi (tagliatelli with fresh porcini mushrooms) or gnocchi di patate in salsa rosa (gnocchi with a creamy tomato sauce).
Hotel La Cisterna, San Gimignano

DAY 3

This morning you leave San Gimignano on foot, following a road with panoramic views of the town’s spectacular towers, which must have been an amazing skyline to medieval pilgrims. Gravel lanes through olive groves and vineyards edged by stone walls lead to the hamlet of San Donato where you are welcomed by the Fenzi family to a farmhouse lunch al fresco. The family-run farm produces its own Vernaccia and Chianti wines and olive oil. The table is waiting and spread with an assortment of seasoned meats, local cheeses, fresh and pickled vegetables, and crostini. 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 is sustenance for a moderate walk 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 you are able to explore the ivy-covered ruins.

This evening you have free time for an independent dinner; choices range from a simple pizzeria, a bustling trattoria, or an elegant restaurant all in the pedestrian center of San Gimignano.
Hotel La Cisterna, San Gimignano

DAY 4

Today begins with a short drive through 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. You ascend a very steep, but short (10-minute) walk into the castle complex, where you are rewarded by browsing the village shops, which include a fine erboristeria (herb shop), sipping a cappuccino, and enjoying a casual panino (sandwich) lunch in one of the town’s cafés.

After lunch, you 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 1,700 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 convenience of an in-town hotel with the ambiance of a country villa, thanks to its pool, spacious grounds, and views. Before dinner at a fine restaurant in town, you may choose to relax by the pool or sip an aperitivo in the garden.
Relais Fattoria Vignale, Radda in Chianti

DAY 5

After breakfast a short bus transfer takes you to the starting point of the walk, midway between Florence and Siena. The walk begins at a point located between the Val di Greve and the Val di Pesa, and proceeds down a quintessential country road dotted with vineyards, olive trees, and farmhouses. The milk of the grazing sheep and goats is 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, its castle was built in the 11th century. Upon arrival you have time to stroll cobbled lanes and alleys before lunch in an inviting country restaurant. A crunchy olive or white-bean-topped crostini might be followed by a plate of homemade ravioli. After lunch you return to the hotel to rest and prepare for an afternoon exploration.

Crucial to understanding the art and history of Tuscany, this afternoon you visit the hill-top city of Siena. A special guest lecturer provides a fascinating introduction to the city’s history and art. The walking tour begins at the Piazza del Campo, the scalloped, slanting main square, unique in Italy, where the famous Palio horserace is held each year. This lively event dating back to the Middle Ages is held in honor of the Virgin Mary and features a series of colorful pageants, a horse race around the sand-covered piazza, and plenty of eating, drinking, and celebrating in the pedestrian streets. You wind through the narrow alleyways to the stunning black-and white-striped marble Duomo, Siena’s cathedral, one of Italy’s great Gothic structures. Inside, the inlaid marble floor comprises 56 panels depicting historical and biblical subjects in the Piccolomini Library, a compact hall off the north aisle built by Pope Pius III to house the books of his uncle, Pope Pius II.

Following this tour, the magical city is yours to enjoy for the evening. Whether you prefer shopping or strolling, the evening will surely culminate with a dinner of classic Tuscan delights; choices range from wild boar and risotto to simple, authentic pizza!
Relais Fattoria Vignale, Radda in Chianti

DAY 6

On your last morning walk you depart the hotel on foot along a country road where you pass working farms as well as luxurious, private villas with landscaped gardens. Cultivated since pre-Roman times by the ancient Etruscans, Tuscan scenery is an example of topography and human activities blending harmoniously. Soon you 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.

After lunch you set out on a short walk to the charming, fortified hamlet of Vertine, which once belonged to the noble, Florentine Ricasoli family. Following a visit of this ancient village, an optional late afternoon walk leads through a cypress-lined lane to the 18th-century noble villa of Vistarenni.

This evening you partake in 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 Benedectine 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, you can visit gardens of aromatic herbs and lemons before a sitting down to a four-course finale to your week, paired with the villa’s own organic wines.
Relais Fattoria Vignale, Radda in Chianti

DAY 7

After breakfast you are escorted to Florence where you bid your group farewell, reflecting on the spirit of Tuscany.

Itinerary Changes

Please bear in mind that this is a typical itinerary, and the actual activities, sites, and accommodations may vary due to season, special events, weather, or transportation schedules. We reserve the right to alter the itinerary since tour arrangements are made up to a year in advance, and unforeseen circumstances that mandate change may arise. Itinerary changes are made to improve the tour and your experience.

Nights 1, 2 & 3

La Cisterna Hotel
San Gimignano, Italy

Nestled in the heart of medieval San Gimignano, this 14th-century property has been owned and operated by four generations of the Salvestrini family since 1918. This evocative three-star hotel delights with vaulted ceilings, chandeliers, and views overlooking either the main square or the valley outside of town.

Nights 4, 5 & 6

Relais Fattoria Vignale
Radda in Chianti, Italy

An atmosphere of relaxed elegance envelops this country manor house dating to the 17th century. Located on the edge of town, this four-star property features expansive grounds bordered by vineyards and olive trees, with spectacular views over the Radda Valley. Additional property amenities include intimate sitting rooms, a heated swimming pool, charming courtyard, restaurants, and a wine shop.

Please note that this is a sample hotel itinerary for this tour. While these exact hotels are featured on most departures, we occasionally reserve other hotels of similar style and quality. If you are currently booked on a Country Walkers adventure, a hotel itinerary has been sent to you for your exact departure date. Please call Country Walkers at 800.464.9255 if you have any questions about the exact hotels selected for any of our tours.

Gianni Stanghellini

Gianni was born in Siena, where he earned a Ph.D. in polar sciences (geology). As a certified walking guide, he enjoys sharing his knowledge about the Tuscan countryside and its beautiful villages with visitors. When not guiding our tours in Tuscany, he is a talented jazz musician, playing both sax and flute!

Angelica Turi

Angelica has been working in the field of art restoration in her hometown of Florence for many years, specializing in paintings on canvas and icons. She is equally comfortable in the Tuscan countryside where her family has been producing wine and olive oil since the mid-19th century. An outdoor enthusiast, Angelica has a deep appreciation of the fine food and wine of Italy, which she gracefully shares on many of our Italian tours.

Florinda Orazi

Born in Rome, Florinda still loves living in her beautiful, bustling city. As a certified walking guide, however, she is able to explore the countryside and satisfy her love of nature. Florinda is also a successful costume and fashion designer, perhaps drawing inspiration from her strong appreciation of art. Meanwhile, her passions for traveling and guiding are motivated by her favorite pastime of meeting people from different countries.

Elena Sardelli

Elena was born and raised in the beautiful Tuscan city of Siena. She is a certified guide for the province of Siena where she shares her love and extensive knowledge of art history. Elena loves nature, different cultures and meeting people. In her "spare time" she studies Events Management, in addition to the Ph.D she already holds in linguistics! She guides our tours in Tuscany, Puglia and the Italian Lakes.

Alessandro Pini

Alessandro makes his home in both Milan and his native Lake Como. Having studied art history, literature and languages, Alessandro is a certified professional guide in Milan, the Italian Lakes and Lombardy region. Fluent in English and German, he is a true Renaissance man who is passionate about sharing his knowledge of Italy with guests on our Piedmont, Tuscany and Italian Lakes tours.

Erika Cennini

A Tuscany native, Erika is a certified city guide of Florence as well as the Province of Siena. Her fondness for all things travel has led her to Paris, London, and just about everywhere in Italy. Erika’s studies reflect her dynamic personality, and include art, architecture, furniture, medieval gardens, and sommelier courses. Fluent in Italian, French, and English, Erika currently resides in the Tuscan hamlet of Poggibonsi where, while not guiding or traveling, she indulges in photography, reading, theater, French cinema, and astrology.

Elizabeth Namack

With her warm smile, Elizabeth Namack brings her love of all things Italian to tours in Tuscany, Umbria, and the Cinque Terre. Elizabeth first came to Italy, and more specifically to Florence, as an American college student to study Italian art history and language. Well, that was almost twenty years ago and she never left! Her active lifestyle and interest in regional wines and cuisines—coupled with her academic background in art history and painting restoration—all help make getting up those hills a little easier—there is a lot to talk about!

Marzia Borghi Rogers

Marzia was born and raised in Tuscany, spending much of her childhood in the shadows of her grandfather, who produced his own wine, and her grandmother, an accomplished chef (surely she has wonderful secrets to share about Italian wine and cuisine). She studied foreign literature and linguistics at the University of Pisa, and also taught college-level Italian for several years while living in the U.K. In addition to being a certified walking guide, Marzia enjoys collaborating with the European Commission on several projects and as a translator.