Tuscany Walking, Cooking and Culture Private, April 23-29, 2023

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OPEN THE DOOR to an Insider Experience 

  • Dates: April 23-29, 2023
  • Accommodations at a historic private villa
  • Private ground transportation to/from Rome Fiumicino Airport
  • Private ground transportation to numerous medieval hill towns and sites
  • Daily walks and visits to medieval hill towns and historic sites
  • Daily cooking, food and wine lessons and demonstrations with local Italians (so fun!)
  • All breakfasts, all dinners and a few lunches
  • Activities and experiences to remember for a lifetime
  • A few surprises!


leisurely hands-on cooking lessons, scenic walks and insider looks at the Italian culture. This is a dream tour for those who love to explore, experience, and enjoy good food with friends.

From the ancient village of Città della Pieve to Tuscany’s spectacular Val d’Orcia, get ready to experience some of Italy’s most breathtaking sites, while immersing yourself in local traditions and food experiences that are nothing less than extraordinary.


Day 1 ~ Sunday, April 23: Arrival

  • Highlights: Arrival, tour of Villa Poggio alla Trese, trip orientation
  • 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 alla Trese, your 17th century villa accommodations near the Tuscan town of Chiusi. After check-in you’ll have the opportunity to explore your surroundings and learn some of the fascinating history of the both the house and the area. Then it’s time to learn how to set up a classic Italian aperitivo – that we all get to enjoy! –  before sitting down for a delicious, regional-style dinner to kick off the tour!

Day 2 ~ Monday, April 24: Pienza, Valiano 

  • Highlights: Pasta lesson, visit to Pienza, cantina visit and wine tasting, sunset aperitivo in the vineyard
  • Breakfast, lunch and dinner

This morning, after a delicious breakfast, you’ll enjoy a picturesque, guided walk through the estate’s olive groves and vineyards, and along the nearby lane. Then it’s time to don an apron for a delightful pasta lesson with chef Lorenza, where you’ll learn to make Tuscany’s traditional pasta, paired with just the right sauce. Lunch will be served right here at the villa, featuring your handmade pasta, of course.

In the afternoon, our drivers will transport you to the Renaissance town of Pienza, situated in the beautiful Val d’Orcia – one of Tuscany’s most photographed areas. With your private guide, Giulia, you’ll first enjoy a walk along the passeggiata di Santa Caterina, with its spectacular views of the valley below, as you make your way into Pienza to explore its winding avenues, learn its fascinating history, and or course to stop in some artisan shops on your way through town.

Afterwards, it’s off to our friends’ 13th century palazzo and wine cantina in the Tuscan countryside, where you’ll spend the rest of the afternoon and evening “in famiglia” as you visit the historic cantina and enjoy sunset aperitivo in the vineyard with its stunning views. Dinner follows, served up right here in the palazzo’s cozy dining hall.

Day 3 ~ Tuesday, April 25: Monteleone, Città della Pieve

  • Highlights: Truffle hunt, walking tour Città della Pieve, saffron tasting, pizza night
  • Breakfast, lunch and dinner

This morning after another delicious breakfast, our drivers will be transporting you to the medieval hill town of Monteleone. Here you’ll be walking a trail, through a beautiful holm-oak forest, from the village itself to the valley below. Along this picturesque route you’ll be taking part in an oh-so-fun truffle hunt with brothers Andrea and Michele and their amazing truffle dog. Afterwards it’s back to the brothers’ charming cafe for a special truffle tastings and lunch – served with local olive oil and wine, of course.

After lunch  you’ll return to the villa for some free time to rest and refresh. Then, later in the afternoon, it’s off to Città della Pieve for a walking tour of this beautifully preserved medieval village, including a visit inside the historic cathedral – housing masterpieces by Renaissance artist, Perugino – ending at a friends’ house for sunset aperitivo. Afterwards it’s off to our favorite pizzeria for a dinner of wood-fired pizzas.

Day 4 ~ Wednesday, April 26: Cortona 

  • Highlights: On your own in Cortona
  • Breakfast and dinner

This morning after breakfast, you’ll be heading to the Tuscan hill town of Cortona for a fabulous on-your-own day! Cortona is rich with shops, museums, walking trails, restaurants and more – there’s something here for everyone.

In the afternoon our drives will be transporting you back to the villa for some rest and relaxation before gathering together in the villa’s “bruschetteria” for an oh-so-fun bruschetta-making lesson – featuring the estate’s exceptional olive oil. Learn the ins and outs of making true bruschetta over wood coals (while enjoying some of the local vino, of course) followed by dinner cooked alle brace (over wood coals).

Day 6 ~ Thursday, April 27: Siena

  • Highlights: Guided tour plus free time Siena
  • Breakfast, dinner

This morning after breakfast, our drivers will be transporting you to beautiful Siena, where you’ll meet up with our expert guide, Giulia, for an amazing tour of this historic town – including a visit inside the breathtaking duomo. Afterwards, you’ll have free time to explore on your own, shop and grab lunch at one of the many inviting restaurants. Giulia will be sure to recommend local specialties!

In the afternoon, it’s back to the villa to relax and recharge before gathering together for a sunset aperitivo and delectable dinner.

Day 6 ~ Friday, April 28: San Casciano dei Bagni 

  • Highlights: Archeological site, aperitivo and lunch at Daniela’s
  • Breakfast, lunch and dinner

After breakfast at the villa, it’s off to the charming village of San Casciano dei Bagni, situated on a picturesque hill, teeming with mineral-rich, hot springs that have been used as thermal baths for centuries. Here you’ll walk your way from the village into the countryside below with our friend, Ludovicio, for a private visit of a newly discovered archeological site, featuring the remains of Roman baths and an ancient temple. Afterwards, it’s on to our friend, Daniela’s chic restaurant, nestled beneath the walls of the castle, for aperitivo and a delicious, Tuscan-style lunch.

After lunch it’s back to the villa where you’ll have time to relax and refresh before gathering together for a special, farewell aperitivo and dinner, featuring some of the region’s most excellent wines.

Day 7 ~ Saturday, April 29: Departure

Early morning departure to Rome Fiumicino Airport


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. 


  • 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
  • Private van service to/from all towns and sites included in the itinerary
  • All regionally inspired dinners with local wines 
  • Most lunches
  • Daily cooking activities
  • Daily countryside or village walks (walks, not hikes!)
  • Entrance fees
  • Guided tours
  • Olive oil tasting
  • Bruschetta lesson
  • Archeological site
  • Truffle hunt
  • Pasta-making lesson
  • Time on your own for shopping and exploring
  • 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

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.

OPEN THE DOOR to an Insider Experience 

  • Dates: April 23-29, 2023
  • Trip Price
    • $3,170 USD per person, single occupancy ensuite
    • $2,970 USD per person, single occupancy with shared bathroom
    • $2,970 USD per person, double occupancy with ensuite bathroom
  • A $500 deposit is required to secure your space on the trip
  • Terms and conditions