Tuscany Layers of History, October 1-7, 2023

A UNIQUE TRIP Experience…

…for those who are looking for more than the average tour of Italy. Our Tuscany Layers of History Tour gives you insider access, like never before – to historic sites that are endlessly fascinating, stunningly beautiful and often unknown – even to locals! From forgotten Etruscan tombs, to priceless Renaissance masterpieces, in countryside churches, each day reveals something surprising and spectacular.

FOLLOWING Secrets and Legends…

From hidden passageways beneath a medieval village to a just-discovered Roman sanctuary to jaw-dropping 3rd century Catacombs, get ready to explore and discover Italy’s ancient history with unprecedented access to sites that most don’t even know exist. Each day you’ll visit castles, churches, ruins and passages, steeped in secrets and legends, while discovering hidden treasures and rarely seen artistic masterpieces.


From mouth-watering pici pasta to Etruscan-style lake perch, each day you’ll enjoy delectable, regional dishes as you explore Tuscany’s layers of history. From the ancient Romans to the famous Medici family, get ready learn how Italy’s culture is woven deeply into its cuisine, as you enjoy local foods, historic recipes and exceptional wines. Buon appetito!


DAY 1: Sunday, October 1: 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 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, October 2: Radicofani

  • Highlights: Guided tour of medieval fortress, visit to historic hamlet, medieval park
  • Breakfast, lunch and dinner

This morning, after breakfast, you’ll be heading to Radicofani, one of Tuscany’s highest points with views the stretch into infinity across the Val d’Orcia. Here we begin with a guided tour of the village, including a stop in the “medieval forest” and a look at precious Della Robbia terracotta masterpieces in the church. Then it’s on to the Rocca of Radicofani. It’s from this fortress that in the 1200s Italy’s infamous bandit, Ghino di Tacco, ruled the areas with his “high-handed deeds”. Later, used as a defensive point by the Duke of Tuscany, the history of Rocca di Radicofani is vast. Here you’ll enjoy a fascinating guided tour – including a change to climb the tower with its stunning views over Tuscany.

After lunch here at the fortress, that includes wine from the local area, it’s back to the villa – along the famous Roman road, Via Cassia – for some free time before enjoying a special farewell apertivo and dinner prepared by Chef Lorenza.

DAY 3: Tuesday, October 3: Chiusi

  • Highlights: Village walk, visit with private guide to underground museum, tombs and catacombs
  • Breakfast, lunch, dinner

This morning, after breakfast, it’s off to nearby Chiusi – one of Italy’s most ancient towns – for a jaw-dropping, private tour with a local guide. From Chiusi’s underground “city” to its panoramic parks (filled with antiquities), you’ll travel from the Etruscan and Roman periods to that of the early Christians – all in the spam of a few short kilometers. These hidden sites can only be visited by appointment and with a guide who specializes in the unique history of this particular area. Then it’s off to nearby Lake Chiusi for a special lunch featuring fresh fish from the lake.

In the afternoon you guided tour continues with a jaunt into the nearby countryside to visit a rare Christian catacomb, before returning to the villa where you’ll have free time to relax and refresh before enjoying a fireside bruschetta-making lesson and aperitivo. Dinner follows, cooked alle brace (over coals).

DAY 4: Wednesday, October 4: Sarteano

  • Highlights: medieval castle, Etruscan tomb site
  • Breakfast, lunch, dinner

This morning, after breakfast, it’s off to the town of Sarteano for a tour inside a the village’s medieval castle, that dates to the 11th century. After a stop at the local coffee bar, we continue to the nearby countryside where you’ll find a spectacular Etruscan necropoli , complete with an ancient cremation site. Afterwards, you’ll continue to the town of Chiusi, where we’ll take a peek inside the unique duomo, on our way to Pino’s trattoria for regionally inspired lunch.

In the afternoon, it’s back to the villa for a bit of rest and relaxation – and perhaps a dip in the pool. This evening we’ll gather together for aperitivo and a delicious dinner prepared by chef Lorenza.

DAY 5: Thursday, October 5: Città della Pieve

  • Highlights: Guided tour of medieval alleyways and grottos, Perugino masterpieces, aperitivo in historic garden, pizza night
  • Breakfast, lunch, dinner

This morning, after breakfast, it’s off to historic Città della Pieve for a full-day immersion into exploring Italy’s treasures. You’ll begin with a fascinating guided walking tour on which you’ll travel from the Etruscan and Roman eras to the medieval and Renaissance periods – all within a few steps! Plus you’ll have private access to a historic wine cantina that once linked secret passageways beneath the town.

After lunch at our friend’s cozy restaurant, it’s back to the villa to relax and refresh. In the afternoon our drivers will transport you back to Città della Pieve for a tour of the several churches that house masterpieces of Renaissance artist, Perugino. You’ll have free time to explore and shop the winding, medieval avenues before we gather together for aperitivo in a private garden to watch the sun set over the Tuscan hills. Then it’s off to our favorite pizzeria for a wood-fired pizza dinner.

DAY 6: Friday, October 6: San Casciano dei Bagni

  • Highlights: Archeological dig
  • Breakfast, lunch, dinner

After a delicious breakfast this morning, put on your walking shoes and grab a sun hat, as we’re off to the picturesque town of San Casciano dei Bagni for a private visit of an active archeological site of a recently discovered Roman sanctuary that is nothing less than astounding. Afterwards we’ll continue to our friend, Daniela’s restaurant, nestled beneath the town’s imposing castle, for a delicious lunch.

In the afternoon it’s time head back to the villa for a bit of rest and relaxation – and perhaps a dip in the pool. This evening we’ll gather together for aperitivo and a delicious dinner prepared by chef Lorenza.

Day 7 ~ Saturday, October 7: Departure

Early morning departure to Rome Fiumicino Airport.


We walk very day on the Tuscany Layer of History Tour, and walking ranges from easy/leisure to moderate. You can expect hard cobblestones, uneven pavement, dust, gravel,  steep steps and 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.


  • 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
  • All regionally inspired dinners with local wines 
  • All lunches
  • Evening aperitivo for chatting, sharing and relaxing
  • Entrance fees to all sites included in the itinerary
  • Private tours and visits with expert, local guides
  • Meal gratuities
  • Activities and experiences to remember for a lifetime

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.


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. 


  • October 1-7, 2023
    • $3,590 USD per person, single occupancy with ensuite bath
    • $3,290 USD per person, single occupancy with shared bath (max 2 persons of same gender per bath)
    • $3,290 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