DAY 1
Arrival Day: Florence. Transfer to San Gimignano; 4 miles, easy with elevation gain of 150 ft
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 de’ 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,
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, you transfer to the
striking town of San Gimignano. 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.
This evening you enjoy a welcome cocktail
before feasting on regional specialties at your
charming in-town hotel.
Hotel La Cisterna, San Gimignano
DAY 2
Villa Pignano to Volterra; 5 miles, easy to moderate. Short village walking tour of Volterra
After breakfast you have a short bus transfer to the
start of a 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, hilltop
town of Volterra. The undulating walk crosses an
exhilarating, open landscape toward Volterra. In
this Etruscan, Roman, and medieval town, your
visit begins with the Etruscan walls and tombs,
and continuing on in history to the Roman baths
and theater. Finally, you stroll along medieval
streets, glimpsing romantic gardens. Time
permitting, you may visit Volterra’s impressive
Etruscan museum.
Following some independent time for strolling
and lunch, you return to San Gimignano in the late
afternoon. There is time to refresh before walking
to dinner at a cozy restaurant in town. The
restaurant is part of the Slow Food Movement, an
international association promoting food and wine
culture, while also protecting local food and
agricultural biodiversity worldwide. Dinner
features a tasty and inventive menu based on dishes
from Etruscan, medieval, and Renaissance times.
Hotel La Cisterna, San Gimignano
DAY 3
San Gimignano to San Donato to Ruins of Castelvecchio; 6 miles, easy to moderate with an elevation gain of 600 ft; 6 miles, challenging afternoon option
You leave San Gimignano on foot, following a road
that provides wonderful views of the town’s
spectacular towers, a perspective on the imposing
and lofty skyline that must have had a striking
effect on medieval pilgrims. You walk through the
rolling countryside of olive trees and vineyards and
continue to the hamlet of San Donato to enjoy a
farmhouse lunch al fresco. This family-run farm
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 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
Castel Petraia to Monteriggioni; 4 miles, easy to moderate. Transfer to Radda in Chianti
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 erboristoria (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
Panzano in Chianti to Volpaia; 3-6 miles, easy to moderate. Transfer to Siena. Two-hour historic city walking tour of Siena
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, the castle was
built in the 11th century. Upon arrival you have
some time to stroll picturesque lanes and alleys, yet
lunch awaits in a lively country restaurant with
homemade soups, crostini, and fresh pasta. 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 lively
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. You
wind through the pedestrian streets making your
way to the 13th-century Duomo (cathedral) with its
striking black-and-white-striped marble facade.
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
Radda in Chianti to San Donato in Perano; 6.5 miles, easy to moderate. San Donato in Perano to Vertine; 1 mile, easy. Fattoria di Vistarenni; 2 miles, easy to moderate afternoon option
After breakfast you leave the hotel on foot through
the heart of the Chianti Classico wine-producing
region. The 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, the walk arrives at the charming,
fortified hamlet of Vertine, which once belonged to
the noble, Florentine Ricasoli family. 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. An
optional walk after lunch leads through a cypress-lined
lane to the 18th-century noble villa of
Vistarenni.
This evening you 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, you can visit gardens of
aromatic herbs and lemons before tasting regional
wines.
Relais Fattoria Vignale, Radda in Chianti
DAY 7
Departure - Florence
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 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.