This is the Italy you always imagined and heard of. With immense historical, cultural and artistic heritage you will be awed as you stroll within the fortified towns of castles and towers. Be amazed by the expressive churches and expan- sive cathedral domes. And find unique shopping down side streets that open up to breathtaking landscapes. Mostly I choose this tour for our Coco’s patrons because of all the time we spend in Umbria. With my repeated travel to this area I think that several days in Umbria would be a preferred experience for you. It has all the charm, beauty and deliciousness of Tuscany, but far fewer tourists. All of the towns you will visit: Orvieto, Spoleto, Assisi, Montefalco and Perugia are totally unique and photo- genic, with charming local shops and their own regional food traditions. And within these walled towns of ruins and legends is great cuisine and cooking traditions that date back thousands of years. Imagine plate after plate of fresh foods, cured meats, giant mounds of fresh ricotta as well as world famous wines. It’s always a good time for a great glass of wine.
This is a great tour for first-time travelers to Italy, with so many sites that you’ve seen in the movies and travel posters you will love this area of Italy. Plus I will be with you too to and ensure you will have a dream vacation.

Chuck Cinelli
Owner of Coco’s Italian Market

Highlights: Tuscany, Assisi, Orvieto, Siena, Florence Cooking Class, Two Winery Visits, Olive Oil Visit Home Hosted Lunch, Private Local Guides

A small deposit reserves your- space-Call Chuck Cinelli at (615) 474-5989

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PDF Brochure of this tour

Day 1 Overnight Flight – Rome

On a journey through Italy’s roads less traveled, discover its endless treasures from Rome to Umbria to Tuscany, and the marvels of wine, cuisine, culture, and history in between.

DAY 2 Rome
Italy’s dynamic capital city beckons. Get a taste of the local culture and start your journey at a delicious welcome dinner.


DAY 3 Rome – Orvieto – Umbria
Olive and cypress trees accent the Etruscan hill town of Orvieto. Stroll the historic streets with a local expert and visit the prominent Gothic cathedral to gaze at a remarkable Signorelli fresco. Continue to discover Orvieto on your own this afternoon. Eat, drink, and disappear into the local scene before taking in the splendors of country life in a pristine Umbrian hill town, your home for the next 3 nights.

DAY 4 Umbria Spoleto – Olive Oil Mill – Umbria
Medieval palaces command the foreground of ancient Spoleto. In the shadow of the Apennines, embark on a walking tour to see centuries of architectural history, from the Ponte delle Torri aqueduct to the gilded elegance of the Duomo of Santa Maria Assunta. Explore more of Spoleto on your own before learning about olive oil at a family-run frantoio (olive presser). Venture into a local restaurant in the Nera Valley, where you’ll enjoy a cooking class in a former 12th-century abbey. Dig in to your handcrafted meal for dinner.

Umbria Cooking Class

DAY 5 Umbria – Assisi – Home-Hosted Lunch
Travel to Assisi, birthplace of St. Francis. Set out on a walking tour of the old city with a local guide, learning about its history as you stroll the medieval streets. Visit the famous Basilica of St. Francis. Later, a local family welcomes you to their country home for lunch as their honored guest. Share stories and make an Umbrian friend (or two).

DAY 6 Umbria – Winery – Pienza
Leave Umbria for the villages of Tuscany, nestled among the vineyards and olive groves of the Val d’Orcia region (UNESCO). Tour a winery’s estate and cellar before indulging in an authentic Tuscan lunch. Created by the on-site chef, this meal is expertly paired with the vineyard’s very own wines. End your day in Pienza (UNESCO), a Renaissance village where flowers and plants adorn the cobblestone streets.

DAY 7 Pienza – Orcia Valley – Bagno Vignoni – Pienza
Journey through the Orcia Valley’s rolling hills on your way to the 12th-century Abbey of Sant’Antimo. Continue on to the unique hamlet of Bagno Vignoni, whose central piazza is filled with thermal water. Taste the flavors of the region at a local pecorino cheese farm. Snack on some of the cheesemaker’s creations before returning to Pienza for an afternoon at leisure. Maybe you’ll explore the countryside along one of the many white roads that cut through the farmland.


DAY 8 Pienza – Siena – Chianti Region

Take a guided walking tour through Siena, delving into the local history as you learn about the world-renowned Palio Horse Race. Enjoy free time to explore more of this hilly town, perhaps visiting its cathedral or the town hall’s frescoes. An afternoon drive through Tuscany’s Chianti Region takes you to the restored Tuscan villa where your hotel is located.

DAY 9 Chianti Region – Florence – Chianti Region
Explore Florence, the “Cradle of the Renaissance,” with a local expert on foot. Wander along the glittering storefronts on the Ponte Vecchio, where gold shops adorn the only Florentine bridge to survive WWII. You’ll also take in the Palazzo Vecchio, the Piazza della Signoria, and Santa Croce. Take some time on your own to explore the city’s seemingly endless treasures, both historic and modern. Return to your Tuscan villa in the evening.

Day 10 Chianti Region – San Gimignano – Chianto Region

Choose how to explore Tuscan landscape because it’s your choice! Join a local truffle hunter in search of the elusive mushroom and sample the goods yourself -OR- take to the countryside on an ATV adventure along winding dirt roads, followed with a taste of truffle bruschetta. Spend your afternoon in San Gimignano, whose beautiful 13th-century medieval towers stand tall over the surrounding vineyards. As the sun begins to set, gather with your fellow travelers for a farewell dinner of Tuscan specialties.


Day 11 Chianti Region – Tour Ends
Your journey through Tuscany and Umbria comes to a close today in your restored Tuscan villa.

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