• Visits to Florence, Siena, and Volterra
• Wine tasting in the heart of the Chianti region
• Medieval and Renaissance architecture and artwork
• Etruscan museum visit
• Classic Tuscan cuisine and accommodations

Walk Rating:

• Easy to moderate terrain with one challenging option and additional mileage
• 6 to 8 miles walking per day with occasional options
• Most walks are on dirt roads, country lanes, or well-maintained trails. Occasionally you will encounter loose stones and tree roots.

Includes:

• Experienced, friendly and knowledgeable guides
• All transportation during the trip
• All accommodations while on tour, including two fine town hotels, all private baths
• All meals included except one lunch and two dinners; alcoholic beverages not included

Meeting Point: Florence, Italy

Departure Point: Florence, Italy

Tour Itinerary

DAY 1
Arrival Day - Florence - San Gimignano; 4 miles, easy with elevation gain of 150’
We 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 Valley. Our 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. We stop for lunch at a quaint local restaurant, overlooking the enchanting landscape. Bucolic country paths bring us to our 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, we transfer to the striking town of San Gimignano. Upon arrival we enjoy an introductory walk of this historic town. As we stroll the alleyways we 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 we enjoy a welcome cocktail before feasting on regional specialties at our charming town hotel.
Hotel La Cisterna, San Gimignano

DAY 2
Villa Pignano - Volterra; 6 miles, easy to moderate. Short village walking tour of Volterra
After breakfast we have a short bus transfer to the start of our scenic stroll through a classic Tuscan landscape. Today’s itinerary offers sweeping views of distant hills as we 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, we begin our visit with the Etruscan walls and tombs. We continue in history to the Roman baths and theater. Finally, we stroll along medieval streets, glimpsing romantic gardens. Time permitting, we may visit Volterra’s excellent Etruscan museum. Following some independent time for strolling and lunch, we return to San Gimignano in the late afternoon. There is time to refresh before we walk to town for dinner at a cozy restaurant that specializes in traditional Tuscan cuisine.
Hotel La Cisterna, San Gimignano

DAY 3
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
We leave San Gimignano on foot, following a road that provides wonderful views of the town’s spectacular towers. The imposing and lofty skyline gives us an appreciation of the effect the sight must have had on medieval pilgrims. We 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 us for our 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; at a simple pizzeria, a bustling trattoria, or an elegant restaurant in the pedestrian center of San Gimignano.
Hotel La Cisterna, San Gimignano

DAY 4
Castel Petraia - Monteriggioni; 5-6 miles, easy to moderate. Transfer to Radda in Chianti
We begin 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. We ascend a very steep, but short (10-minute) walk into the castle, but we are rewarded by browsing the village shops, which include a fine erboristoria (herb shop), sipping a cappuccino in the main square, and enjoying a casual panino (sandwich) lunch in one of the town’s cafés. After lunch, we drive approximately one hour to our 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. Our 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, we may choose to relax by the pool or sip an aperitivo in the garden. Relais Fattoria Vignale, Radda in Chianti

DAY 5
Panzano in Chianti - Volpaia; 5 miles, easy to moderate. Transfer to Siena. Two-hour historic city walking tour of Siena
After breakfast a short bus transfer takes us to the starting point of our walk, midway between Florence and Siena. Our walk begins at a point located between the Val di Greve and the Val di Pesa, and takes us 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 we see our 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 we have some time to stroll picturesque lanes and alleys, yet lunch awaits us in a lively country restaurant with homemade soups and fresh pastas. After lunch we return to our hotel to rest and prepare for our afternoon exploration. Crucial to understand the art and history of Tuscany, this afternoon we visit the hill-top city of Siena. Our 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. We wind through the pedestrian streets making our way to the 13th-century Duomo (cathedral) with its striking black-and-white-striped marble facade. Following our 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!
Relais Fattoria Vignale, Radda in Chianti

DAY 6
Radda in Chianti - San Donato in Perano; 6.5 miles, easy to moderate. Fattoria di Vistarenni; 2 miles, easy to moderate afternoon option. Evening visit and wine tasting at Badia a Coltibuono
After breakfast we depart from our hotel on foot through the heart of the Chianti Classico wine-producing region. Our walk begins on a country road where we 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, our walk takes us to the charming, fortified hamlet of Vertine, which once belonged to the noble, Florentine Ricasoli family. Soon we 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 us through a cypress-lined lane to the 18th-century noble villa of Vistarenni. This evening we 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 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, we visit gardens of aromatic herbs and lemons before tasting regional wines. Relais Fattoria Vignale, Radda in Chianti

DAY 7
Departure - Florence
After breakfast we escort you to Florence and bid farewell, reflecting on the spirit of Tuscany.

Itinerary Changes
Please bear in mind that this is a typical itinerary, and the actual walks and sites may vary due to season, special events or weather. 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.
 

Rates & Departure Dates

Tour: 7 Days

Departure Dates:
Sun., May 11, 2008
Sun., May 18, 2008
Sun., June 01, 2008
Sun., June 08, 2008
Sun., September 07, 2008
Sun., September 21, 2008
Sun., October 05, 2008
Sun., October 12, 2008

Price From:  $3,598
Single Supplement:  $425

Nights One, Two & Three:
LA CISTERNA HOTEL
San Gimignano, Italy
Nestled in the heart of medieval San Gimignano, this evocative hotel delights with views overlooking either the main square or the valley outside of town.

Nights Four, Five & Six:
RELAIS FATTORIA VIGNALE
Radda in Chianti, Italy

An elegantly restored fine hotel on the edge of town. Expansive grounds that overlook the Radda Valley offer a heated swimming pool and charming courtyard. Additional property amenities include common rooms, 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.