Exploring Italy's Treasures, May 22-28, 2022

WE’VE PULLED OUT all the Stops… 

…to create a one-of-a-kind trip experience for those who are looking for more than the average tour of Italy. On this unprecedented trip itinerary, you get insider access, like never before – to sites that are endlessly fascinating, stunningly beautiful and often unknown – even to locals!

BECOME Part of the Family 

Get ready to become an honorary member of the local community, as our team is made up of local experts, guides and private residents. In fact, you’ll become a part of an extraordinary family, so to speak, intent on preserving and celebrating Italian culture, while shedding light on Italy’s hidden treasures, many of which are in danger of fading away into history.

Of course you’ll also enjoy unforgettable camaraderie, an energetic atmosphere and delectable meals – a hallmark of Strada Toscana tours.

BE an Insider 

Every day, on this extraordinary itinerary, we’re teaming up with local guides & artisans, private residents, plus our own local chapter of Italy’s National Trust, Fondo Ambiente Italiano (FAI), to bring you a truly exceptional trip experience.

What is FAI? It is a private, non-profit organization with a steadfast purpose to protect Italy’s culture, history and art treasures, which might otherwise be lost. Through Strada Toscana’s special partnership with the organization, we are able to offer you exclusive access to incredible historic sites, hidden treasures, and artistic masterpieces – most of which are not even known by the general public.

GET READY to Explore!

Each day you’ll be visiting castles, abbeys, churches, hamlets, ruins and parks, steeped in history. You’ll discover hidden treasures, rarely seen artistic masterpieces and historic sites that are only accessible with the assistance of local residents, friends and our partner members at FAI.

This also means that you can expect to be walking every single day, and there are times when we might be out and about exploring and touring sites for much of the day. Walking ranges from easy/leisure to moderate, and you can expect hard cobblestones, uneven pavement, steps and steep hills. We caution that this trip is not the right fit for those who have difficulty walking or have a health-related condition that would limit participation and/or impede or inconvenience the rest of the group.


DAY 1: Sunday, May 22: Arrival

  • Highlights: arrival and welcome
  • Dinner

Benvenuti in Italia! Upon arrival at Rome Fiumicino Airport, sit back and relax as you are transported by private van service to the Italian countryside and Poggio alle Trese, your charming and historic accommodations for this one-of-a-kind journey. After check-in, you’ll have the opportunity to explore your surroundings and learn some of the fascinating history of the both the structure and the area from your Strada Toscana hosts. This evening you’ll enjoy a classic Italian aperitivo with your fellow travelers, followed by a special welcome dinner prepared by our own chef Lorenza.

DAY 2: Monday, May 23: Città della Pieve

  • Highlights: Walking tour Città della Pieve, coffee bar, saffron tasting, underground visit of private grottos, pizza night
  • Breakfast, lunch, dinner

This morning, after breakfast, our drivers will be taking you to nearby Città della Pieve for a fascinating walking tour with local guide, Bianca, who knows all the best-kept secrets of this unspoiled hill town and its history. First stop is the centuries-old duomo, with its ancient catacombs, medieval foundations and unique, frescoed interior. After a pit stop at our friends’ coffee bar, you’ll continue along some of Città della Pieve’s fabulous, winding avenues – including the narrowest alleyway in Italy – before making your way to our friend, Alessandro’s, saffron shop to enjoy an oh-so-fun saffron tasting and light lunch – so surprising and fun!

After lunch it’s back “home” to relax for a bit, before meeting up again with Bianca, as she takes you special insiders’ tour of town, including tucked-away churches and convents, where you’ll discover breathtaking masterpieces by Renaissance artist, Perugino, and others. Afterwards you’ll have some free time to wander on your own before taking an astounding tour of underground grottos, hidden beneath private homes. Aperitivo happens right here, in a private grotto, before continuing to Lorenza’s restaurant for pizza making and dinner!

DAY 3: Tuesday, May 24: Mongiovino, Piegaro, Panicale

  • Highlights: Visit to Mongiovino, historic glass museum, walking tour Panicale
  • Breakfast, lunch, dinner

This morning, after breakfast, it’s off with a local member of FAI to a tucked away, historic hamlet that even locals don’t know exists! Mongiovino is perched in a panoramic location, with sweeping views of Lago Trasimeno, and its precious, centuries-old church (with recently restored frescoes) will be opened up just for your private viewing. After our walk around the village, it’s time for a coffee break at the local bar before continuing on to nearby Piegaro – once famous for its glass-making factories that specialized in green wine bottles and traditional demijohns. All that remains of this centuries-old industry is a small, but excellent museum, where you’ll get a fascinating glimpse back in local history.

Afterwards, it’s back to the villa for lunch on the terrace, followed by some time for rest and relaxation. In late afternoon, our drivers will be taking you to nearby Panicale to meet up with your new friend, Bianca, and to enjoy a private walking tour of this historic medieval hill town. Aperitivo and dinner are right here, overlooking the town’s adorable main piazza.

DAY 4: Wednesday, May 25: Orvieto

  • Highlights: Orvieto underground, duomo di Orvieto, chiesa of the Abbadia
  • Breakfast, dinner

This morning, after breakfast at the villa, it’s off to the splendid town of Orvieto, perched on a dramatic bluff of tufo, and with foundations that date back to Etruscan times. First stop, with your friend and local guide, Bianca, is an underground tour, where you’ll gain fascinating insights into Orvieto’s layers of history. Then, enjoy some time on your own to visit the magnificent 13th century cathedral (a must see!), browse the many inviting shops, explore the town’s endless medieval avenues and choose the ideal cafe or trattoria for lunch.

In afternoon we gather together at the duomo to continue just outside of town to the stunning Abbadia di Orvieto and its beautiful roofless cathedral and mosaic-floored chapel. Aperitivo will be enjoyed right here in the restful courtyard with its romantic, vine-covered walls. Dinner this evening will be served up by chef. Lorenza, back at the villa.

DAY 5: Thursday, May 26: Sarteano, San Casciano dei Bagni

  • Highlights: Etruscan necropoli, Castello di Sarteano, tour of San Casciano and Roman thermal pools, vineyard aperitivo & dinner
  • Breakfast, lunch, dinner

After another delicious breakfast this morning, put on your walking shoes and grab a sun hat, as we’re off to explore an incredible Etruscan necropoli, nestled in a Tuscan hillside, overlooking the stunning Val d’Chiana. After peeking in some tombs that date back nearby 3,000 years, we continue on to the nearby town of Sarteano for a tour of its imposing medieval castle – complete with crenellated ramparts. After all this exploring and climbing it’s time head back to the villa for lunch and a bit of rest and relaxation – and perhaps a dip in the pool.

In late afternoon, we head out for a very special evening in the village of San Casciano dei Bagni, where you’ll enjoy a walk to an amazing archeological site of Roman thermal pools, fed by a rich source of hot springs, including the recently discovered ruins of a temple dedicated to Apollo. A few more minutes and we come to our friends’ vineyard where you’re in for a treat as we enjoy aperitivo and a grilled dinner, right here amongst the grape vines.

DAY 6: Friday, May 27: Montegiove

  • Truffle hunt, tour of private castle, estate wine tasting
  • Breakfast, lunch and dinner

This morning, after breakfast, you’ll be heading into the dense forests of Umbria to meet our friend, Lorenzo, the Marquis of the Castello di Montegiove, and to venture onto his private land with a local tartufaio – truffle hunter – and his truffle-hunting dogs. Here’s hoping you find some precious truffles! Afterwards, it’s back to the castle (which dates to the 1200s) to enjoy a private, guided tour of its medieval rooms and wine cantina. A light lunch and wine tasting follows, featuring the estate’s excellent wines, along with fresh truffles from the truffle hunt. After lunch it’s off for gelato at one of our favorite gelato shops!

This afternoon you’ll have time on your own to relax by the pool or take a walk along the countryside lane. Then it’s time for a special farewell “aperi-cena”, with a delightful variety of dishes and wines.

Day 7 ~ Saturday, May 28: Departure

Our drivers will be transporting you this morning to Rome Fiumicino Airport.

Here’s an overview of what you can expect.

  • Private visits to historic churches, abbeys and sanctuaries with precious frescoes and hidden crypts
  • Accompaniment by local guides and FAI representatives
  • Exclusive access to historic sites
  • Castles, castles, and castles! From crenellated towers to walled hamlets, get ready to walk the ramparts – literally
  • Private, invitation-only lunches, aperitivi and wine tastings
  • Guided visits to local museums that house little-known, micro-zone histories
  • Viewings of priceless masterpieces by artists, such as, Perugino, Raffaello and Signorelli
  • Truffle hunt with tartufaio and his truffle dogs
  • Vineyard aperitivo and dinner
  • Tour of Etruscan necropolis, Roman baths and newly uncovered archeological site
  • Evening aperitivo hour for reflecting and sharing
  • Chef-prepared dinners

Get ready to be flexible! On the Exploring Italy’s Treasures Tour, our daily trip outings might be adjusted as we go along.

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.


  • 7 days/6 nights at elegant Villa Poggio alla Trese, situated in the picturesque countryside near the charming Tuscan hill town of Chiusi 
  • Group transportation by private van service to/from Rome Fiumicino Airport on arrival and departure dates
  • Daily, private ground transportation to/from all medieval hill towns, sites and locations included in the itinerary
  • All breakfasts, featuring fresh-baked Tuscan pastries, organic sheep milk yogurt, local cheeses, seasonal fruits, organic cereals and fresh eggs, plus juices, herbal teas and Italian coffee
  • All regionally inspired dinners with local wines 
  • All lunches
  • Activities and experiences to remember for a lifetime
  • Accompaniment by Pamela Haack, along with team Strada Toscana
  • Entrance fees to all sites
  • Guided tours
  • Wine tasting
  • Olive oil tasting
  • Evening aperitivo hour for chatting, sharing and relaxing

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


Your accommodation are Poggio alle Trese, a 17th century villa, nestled along the border of Tuscany and Umbria, near the town of Chiusi (Tuscany). The villa boasts two kitchens, several lounge areas, dining hall, breakfast hall, sleeping rooms decorated with family antiques, swimming pool, outdoor patios, barbecue “house”, gazebo, wisteria-covered aperitivo terrace and so much more… View photos of Villa Poggio alle Trese here. 


  • May 22-28, 2022
    • $2,800 USD per person, single occupancy with ensuite bath
    • $2,650 USD per person, single occupancy with shared bath (max 2 persons of same gender per bath)
    • $2650 USD per person, double occupancy with ensuite bathroom
  • $500 deposit is required to book your space on this tour
  • All sleeping rooms are private. Some sleeping rooms share a bathroom (max 2 of same gender per bathroom)
  • Maximum 12 participants
  • No added fees