Since ancient times, Italy has been a center of artistic and culinary delights and nowhere is this more evident than in the regions of Tuscany and Umbria. Siena, San Gimingnano, Pienza and Assisi— all UNESCO World Heritage Sites— are just a few of the stops along our road of discovery. We have arranged the itinerary to allow time to explore the incredible areas you’ll see, and taste the local cuisine. The riches of the region will be apparent as you hike, explore and eat your way through some of Italy’s most beautiful and inspirational scenery and cities of art.
If you’ve been yearning to read the book on your shelf that your best friend recommended months ago... If you want to perfect your European siesta technique while lying next to a glorious pool... If you’re a die-hard hiker who longs to explore an historical countryside that beckoned to both St. Francis of Assisi and the Roman emperors of legend and fact... If you are a complicated soul who delights in variety and exploration... then this is your tour.
This is a tour designed specifically for people like us who possess a dichotomous nature in which opposites are not only welcomed, but nurtured. We delight in a luxurious meal enhanced a bevy of local wines, but we also feel that this meal can be lifted into the sublime if it’s been preceded by a day hiking through the hills, absorbing the ambiance. A hard day of physical exertion is every bit as rewarding as a day lounging pool side, lost in the deep colors of the Mediterranean.
Carpe Diem!
Tuscany & Umbria:
Cooking and Walking Tour:
Day one
We will meet you at the train station in Poggibonsi,
just outside Florence and shuttle you to Poggio Alloro.
After settling in, we’ll partake of San Gimignano
historic views while sipping a welcoming glass of
Vernaccia, heralding the beginning of our tour in Italy.
The late afternoon will be spent sauntering around San
Gimignano, a UNESCO World Heritage Site, for a few hours
before returning to our inn to enjoy for our welcoming
dinner. Lodgings: Fattoria Poggio Alloro, San Gimignano.
Tuscany & Umbria:
Cooking and Walking Tour:
Day two
Today we’ll explore the life and moods of old Italy
behind the medieval walls of Siena, another UNESCO World
Heritage Site. With our guide, you’ll explore a city
that is simply fascinating. We’ll assume a leisurely
pace, so you’ll have time to linger. We’ve been
many times, but Siena still surprises us, and we delight
in every step. Such Old World charm! A visit to Siena is
never complete, though, without a stop at Enotica
Italiana, which offers an excellent selection of Italian
wines and a cool, refreshing gelato on the most famous
of piazzas, Piazza del Campo. The day will end with a
sumptuous dinner at one of the region’s best
restaurants. Lodgings: Hotel Santa Caterina, Siena
Tuscany & Umbria:
Cooking and Walking Tour:
Day three
A full day is planned, with visits to two of Tuscany’s
famous hill top towns, and the historical Abbey Sant'
Antimo. First, we’ll hop in the van for a quick shuttle
to wine country extraordinaire — the classical hill top
town of Montalcino, home of Brunello, one of the world’s
greatest wines. From Montalcino, we’ll begin a 3-hour
hike to the Sant’Antimo Abbey. (For anyone interested in
spending more time exploring the town, and perhaps
sampling the famous wines of the region, the van will
meet up with the hikers at the Abbey).
Sant’ Antimo is a glorious monastery, isolated in a timeless landscape of fields, olive groves and wooded hills. Our hike will arrive at the Abbey in time to experience Sext, the noon prayer service that is still performed by the monks in a haunting Gregorian chant. This is the only place in Italy where the practice still continues, as it has for centuries. Afterwards, well enjoy an amazing lunch at our favorite trattoria, which sits just above the Abbey. Then it's on to the Citta Ideale of Pienza — our third UNESCO World Heritage Site in three days! — which was setting for both Minghella’s The English Patient and Zeffirelli’s Romeo & Juliet. Pienza is also the historical home of Tuscany's cheese industry, and Pecorino is abundant. So, of course, we’ll enjoy its many incarnations before ending our day. Lodgings: Chateaux Relais Il Chiostro di Pienza, Pienza
Tuscany & Umbria:
Cooking and Walking Tour:
Day four
We move on to Umbria, Tuscany’s charming, subtle
brother. After breakfast, we’ll jump in the van for a
short drive to Cortona, the setting for Under the Tuscan
Sun. We will take the morning to explore this lovely
town, which is brimming with many historic & culinary
delights. A hike to Cortona’s summit is a must, for
you’ll pass by the mock-Romanesque church, Santa
Margherita and Fortezza Medicea. We will enjoy lunch in
Cortona, and taste many famous olive oils and balsamic
vinegars from this area. Afterwards we’ll head to the
quaint residence of Villa Il Poggiolo for an afternoon
cooking class. For dinner tonight, we’ll experience the
utter perfection of Italian pasta… but only after we
learn to make it! Lodging: Villa Il Poggiolo, Perugia
Tuscany & Umbria:
Cooking and Walking Tour:
Day five
A quick shuttle will bring us to Assisi, once the home
of the great Saint Francis, and our fourth UNESCO World
Heritage Site, if you’re counting (and we think you
should!) Here you will have a chance to view the superb
Giotto frescos at the Basilica of San Francesco d'Assisi
before we hike to Spello, a charming little town nestled
on an Umbrian hillside. Amazingly, Spello is filled with
art, and home to fascinating collections by
Pinturrichio, Il Perugino and Norberto Proietti. We’ll
end the afternoon with a wine- and food-tasting at
Enoteca Properzio, hosted by Roberto Angellini. Here you
will sample many of Umbria’s best wines, and the many
pestos, cheeses and olive oils that have made the region
justifiably famous. Lodging: Villa Il Poggiolo, Perugia
Tuscany & Umbria:
Cooking and Walking Tour:
Day six
After a morning trek through the olive groves and
vineyards, we’ll explore Perugia — Umbria’s capital —
which is home to an ancient medieval aqueduct, and
subterranean city. We recommend spending several hours
exploring the many hidden tunnels and paths of the old
city before moving above ground to the citta d’arte. And
as if that wasn’t enough, Perugia is also a city for
chocolate, for the world-famous Baci kisses are made
right here.For the culinarily inclined, we’ll again
enjoy an afternoon cooking class with Christina, leading
to another exceptional dinner this evening. Lodging:
Villa Il Poggiolo, Perugia
Tuscany & Umbria:
Cooking and Walking Tour:
Day seven
Southern Umbria is home to Orvieto, which has been
celebrated since the Renaissance for its colorful
ceramics and delicious white wine. Orvieto is an
Etruscan town, perched dramatically on a cliff, and it
dominates the valley far below. These cliffs are made up
of soft tufo stone, so soft and malleable that it has
been used to carve out tombs since ancient times. En
route back to our inn, we’ll stop for a tasting of the
region’s olive oils, and a tour of the olive groves.
Then we’ll return to Villa Il Poggiolo, where
Christina’s will be serving a special farewell dinner
that will celebrate the new friendships we’ve made.
Lodging: Villa Il Poggiolo, Perugia
Tuscany & Umbria:
Cooking and Walking Tour:
Day eight
After we reminisce about our adventures at our good-bye
breakfast, we’ll head back to the Perugia train station
and to begin a journey homeward — or beyond! We hope
that all your travels will be so blessed.
