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.

Day 1

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.

Day 2

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

Day 3

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

Day 4

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

Day 5

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

Day 6

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

Day 7

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

Day 8

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.