TUSCANY & UMBRIA Cultural Adventure

Join Paola Donzelli for a new journey through Tuscany and Umbria inspired by the places, flavors, and traditions she knows and loves best. A longtime member of the Strada Toscana team, Paola is a passionate and experienced trip leader with deep roots in both regions, and has a wonderful way of bringing Italy to life through its people, history, food, and everyday traditions. And as a certified sommelier, her love and knowledge of Italian wine adds another special dimension to a week filled with memorable meals, local discoveries, and meaningful experiences.

Centered in the medieval hill town of Città della Pieve, this is an all-new Strada Toscana itinerary, created around new destinations, fresh experiences, and local connections we haven’t featured before. Each day, Paola will lead you through a different side of Tuscany and Umbria, from the stunning churches and abbeys of Perugia to the sweeping vineyards of Montalcino, the fascinating Etruscan history of Chiusi, the timeless beauty of Cortona, and the quiet charm of villages tucked into the countryside.

ALONG THIS JOURNEY You’ll Discover…

…Renaissance masterpieces in Perugia, celebrated Brunello wines in the hills of Montalcino, remarkable underground Etruscan museum that many travelers never even know exists, and carefully crafted food-and-wine pairings with Paola and Cristian. You’ll also explore the ancient thermal village of Bagno Vignoni, discover local saffron traditions in Città della Pieve, and join local experts for a truffle hunt in the Umbrian countryside.

Food and wine are woven naturally throughout the week, from leisurely lunches and beloved regional specialties to exceptional wines and memorable meals that reveal the character of each place we visit.

TRIP ITINERARY

Day 1 ~ Arrival

• Highlights: Welcome and trip orientation
• Dinner

Benvenuti in Italia! Upon arrival at Rome Fiumicino Airport, sit back and relax as you are transported by our private drivers to your beautiful accommodations in the village of Città della Pieve – your home base for the fabulous days ahead! After check-in you’ll have the opportunity to explore your surroundings with your trip host, and learn some of the fascinating history of the area. Then it’s time to learn how to set up a classic Italian aperitivo, before sitting down for a delicious, regional-style dinner to kick off the tour.

Day 2 ~ Perugia, the Heart of Umbria

• Breakfast, lunch, dinner

Today we’ll explore Perugia, Umbria’s vibrant capital, a city shaped by Etruscan origins, medieval streets, Renaissance art, and a lively café culture.

Our day begins with an ascent into the heart of Perugia’s historic center through centuries-old tunnels. Once above, we’ll pause at a favorite local coffee bar before setting out with our knowledgeable guide, Bianca.

Beginning in the magnificent Piazza IV Novembre, home to the Fontana Maggiore and the Cathedral of San Lorenzo, Bianca will introduce us to Perugia’s remarkable history as we wander its elegant streets, discover striking Renaissance masterpieces, and take in the city’s distinctive medieval architecture.

We’ll then enjoy lunch at a local restaurant featuring regional Umbrian specialties.

In the afternoon, we’ll visit the magnificent Abbazia di San Pietro, where we’ll admire its richly decorated basilica and stroll through the peaceful medieval herb garden.

Returning to Città della Pieve in the late afternoon, we’ll have time to relax before gathering for dinner at one of the town’s inviting local restaurants—the perfect ending to a day filled with history, art, beauty, and the flavors of Umbria.

Day 3 ~ Montalcino, Brunello & Bagno Vignoni

• Breakfast, lunch, light dinner

This morning we venture into the heart of Brunello country, where vineyards blanket the rolling hills surrounding the enchanting hill town of Montalcino.

Our morning begins with time to explore this beautifully preserved medieval village. Stroll its charming stone streets, browse inviting artisan shops and wine boutiques, and take in sweeping views across the Tuscan countryside from the ancient fortress. Montalcino’s rich history and relaxed atmosphere make it one of Tuscany’s most beloved destinations.

We’ll then visit a local winery, where generations of winemakers have cultivated Sangiovese grapes in the unique soils and climate that have made Brunello di Montalcino one of Italy’s most celebrated wines. Enjoy a guided tour of the estate, learn about the traditions of Brunello production, and savor a leisurely lunch accompanied by a tasting of the winery’s exceptional wines.

On our return to Città della Pieve, we’ll make a stop in the charming village of Bagno Vignoni. Since Roman times, the healing waters of this village have attracted pilgrims, nobles, artists, and travelers making their way through Tuscany. Today, the village retains its timeless charm, inviting visitors to wander its quiet streets and imagine centuries of life centered around its remarkable thermal springs.

We’ll arrive back in Città della Pieve in the late afternoon, leaving time to relax before enjoying an informal apericena at our friends’ charming cafe.

Day 4 ~ Village Life, Truffles & Saffron

• Breakfast, lunch & aperitivo

Today offers an authentic glimpse into life in a medieval hill town.

We’ll begin by visiting several of Città della Pieve’s beautiful churches and cathedral, home to remarkable Renaissance art and centuries of local history.

Next, we’ll travel to the nearby village of Monteleone d’Orvieto for one of the week’s highlights—a guided truffle hunt through the surrounding woodlands with trained dogs and local experts. Discover why these prized delicacies have been treasured for centuries before enjoying an abundant truffle-inspired lunch featuring the day’s discoveries and other regional specialties.

Returning to Città della Pieve, the afternoon is yours to enjoy at your own pace. Wander the charming medieval streets, browse artisan boutiques, relax with a gelato or a glass of wine in one of the piazzas, or simply soak in the unhurried atmosphere of this enchanting hill town.

As evening approaches, we’ll gather for a private visit to Alessandro’s saffron shop, where you’ll discover how this precious spice has been used Città della Pieve for centuries. Enjoy a tasting of the spice while you learn about its cultivation, history, and importance to the region. The remainder of the evening is yours to enjoy dinner at your leisure in one of the town’s inviting cafés or restaurants

Day 5 ~ Ancient Chiusi & Wine and Food Pairings

• Breakfast, lunch, dinner

Today we step back more than 2,500 years into the fascinating world of the Etruscans.

Our destination is Chiusi, once one of the twelve great cities of the Etruscan civilization. We’ll explore its remarkable archaeological treasures and discover how these sophisticated people shaped much of early central Italy long before the rise of Rome.

Lunch features one of the area’s most unique culinary traditions—Brustico, freshwater fish grilled over reeds using a cooking technique that dates back generations.

In the afternoon, we’ll return to Città della Pieve where you might rest and relax or enjoy a passeggiata to the nearby park.

This evening becomes one of the culinary highlights of the journey as Paola and Cristian host a memorable food and wine pairing dinner. Drawing upon Paola’s expertise as a certified sommelier, each course is thoughtfully paired with exceptional regional wines while stories of local traditions, producers, and culture enrich the experience.

Day 6 ~ Cortona Under the Tuscan Sun

• Breakfast, dinner

Our final full day takes us to the beautiful hill town of Cortona, dramatically perched above the Val di Chiana.

Our first stop is the peaceful Eremo Le Celle, a 13th-century hermitage nestled in a wooded valley just outside the town. Founded by St. Francis of Assisi, this tranquil sanctuary remains one of Tuscany’s most inspiring spiritual sites. As you stroll its quiet pathways with Bianca, you’ll discover the simple stone cells where Francis and his followers once lived, surrounded by the serenity of nature.

We then continue into the heart of Cortona, where Etruscan origins blend seamlessly with Renaissance elegance. Wander its charming piazzas, narrow cobblestone streets, artisan boutiques, and inviting cafés while enjoying sweeping views across the Tuscan countryside. Fans of Under the Tuscan Sun may recognize several of the town’s picturesque corners, but Cortona’s true charm lies in its centuries of history and authentic Italian character.

After time to explore and shop at your leisure, enjoy lunch on your own at one of Cortona’s inviting cafés or trattorias. Bianca will be delighted to recommend some of her favorite local spots.

Returning to Città della Pieve in the afternoon, you’ll have time to relax, do a bit of last-minute shopping, or prepare for tomorrow’s departure.

This evening we’ll gather one last time for a festive farewell aperitivo followed by a special dinner celebrating the friendships, laughter, and unforgettable experiences we’ve shared throughout the week. As we raise our glasses together, we’ll toast not only the beauty of Tuscany and Umbria, but the memories that will travel home with us long after the journey ends.

Day 7 ~ Departure

Early morning departure for Rome Fiumicino Airport

INCLUSIONS

• 7 days/6 nights stay Boutique Hotel Vannucci in Città della Pieve
• Group transportation by private transport service to/from Rome Fiumicino Airport on arrival and departure dates
• Private transport service to/from all towns and sites included in the itinerary
• All breakfasts
• 5 dinners
• 4 lunches
• Daily accompaniment with trip host, Paola Donzelli
• Private guided walking tours with Bianca
• Visit to 14th century Abbazia di San Pietro in Perugia
• Tour of Montalcino winery & Brunello wine tasting
• Private tour of archeological site & museum in Chiusi
• Food and wine pairings dinner
• Saffron tasting & aperitivo
• Truffle hunt & truffle inspired lunch
• Visit to le Celle Hermitage, Cortona (founded by Saint Francis of Assisi)
• Free time for shopping and exploring

Not included: Airfare, meals, alcoholic drinks, buses, trains or boat transportation outside of that which is specifically listed in the trip package, gratuities for villa staff and drivers

The Unexpected is Part of the Journey: At Strada Toscana we weave amazing, authentic experiences into every trip, but sometimes unexpected things come up. If a site has an unscheduled closing, we improvise to include something equally as wonderful and interesting. The quality of the trip is never at risk, as our team is committed to excellence, along with our vast, local, Italian connections.

ACCOMMODATIONS Boutique Hotel Vannucci

Hotel Vannucci began as a project of Vittoria Spinola, daughter of King Vittorio Emanuele II, who fled Pisa (and an arranged marriage with her elderly husband) to start a new life with her lover in Città della Pieve. Here, she and her soon-to-be new husband, Paolo, built two villas that became luxurious holiday accommodations for wealthy Romans vacationing in the countryside. In 1903 one of the villas became Hotel Vannucci, and today it maintains the elegance and refinement of its inception, with luxurious sleeping rooms, marble bathrooms and inviting gardens. A stay here is truly special, nestled just outside the medieval walls of the historic, and unspoiled, village of Città della Pieve. 

VIEW the Photo Gallery

DATES & DETAILS

• Dates: October 10-16, 2027
• Room Price & Description:
  • $3,795 USD – Single Occupancy Single: Single bed, private ensuite bathroom
  • $3,995 USD – Single Occupancy Classic: Double bed, private ensuite bathroom with walk-in shower
  • $4,295 USD – Single Occupancy Superior: Double bed, private ensuite bathroom with tub/shower combination
  • $3,795 USD – Double/Twin Occupancy Superior: Double bed or two singles, private ensuite bathroom with tub/shower combination
  • $3,895 USD – Double/Twin Occupancy Deluxe: Double bed or two singles, private ensuite bathroom with tub/shower combination + sitting area
• $700 Deposit, per person, is required to secure your space on this tour
• Terms and Conditions

BOOK NOW