Tuscany Walking, Cooking & Culture, May 29 - June 4, 2022

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OPEN THE DOOR to an Insider Experience 


leisurely lunches in regal castles, 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 magical village of Bagnoregio on its golden bluff, to Tuscany’s spectacular Val d’Orcia with its medieval hill towns, 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, May 29: 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, May 30: Pienza & the Val d’Orcia

  • Passeggiata di Santa Caterina, walking tour of Pienza, pecorino tasting, olive grove walk & bruschetta-making lesson
  • Breakfast, lunch and dinner

This morning after a delicious breakfast, it’s off to the gorgeous Val d’Orcia, one of Tuscany’s most photographed areas. Along with your private guide, you’ll enjoy an invigorating walk along the stunning passeggiata di Santa Caterina, with its spectacular views of the valley below. Then it’s on to the town of Pienza – a Renaissance gem – to explore its winding avenues, learn its fascinating history, and or course to stop in some artisan shops on your way through town. For lunch we continue to our friends’ organic sheep farm where you’ll enjoy a light lunch along with a tasting of pecorino cheeses – a delectable specialty of the area.

In the afternoon, it’s back to the villa for some free time followed by a walk through the nearby olive grove, followed by 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)! Afterwards, our friend, Alessandro will be grilling your dinner the Tuscan way – alle brace (over wood coals).

Day 3 ~ Tuesday, May 31: Ficulle

  • Walking tour of Ficulle, hand-made cookware demo with Fabio, herb “walk” and salty biscotti lesson
  • Breakfast, lunch and dinner

This morning after breakfast, we’ll be heading along a picturesque road to the ancient village of Ficulle, perched on a spectacular ridge line overlooking the rolling hills of Tuscany. Here you’ll take a walk around town before meeting up with our friend, Fabio, for a look inside an incredible medieval church (Fabio holds the key!), all followed by a fascinating demonstration of his hand-thrown cookware called coccio. For centuries the town of Ficulle was a center of pottery used specifically for cooking, and Fabio is the last remaining ceramist of this unique, rustic cookware. Afterwards, you’re in for a treat as we head to Fabio’s restored wine cantina for a special lunch, cooked and served in Ficulle’s “coccio”.

After lunch it’s back to the villa for some time to relax, or perhaps you’d prefer to stretch your legs on a walk. Then it’s time to don an apron as you enjoy a fascinating herb lesson with Lorenza, along with a chance to bake some of Lorenza’s favorite salty, herb biscotti. Aperitivo follows, along with another fabulous dinner featuring local, organic produce.

Day 4 ~ Wednesday, June 1: Città della Pieve

  • Walking tour Città della Pieve, saffron tasting, truffle hunt, pizza night
  • Breakfast, lunch and dinner

This morning after another delicious breakfast, our drivers will be transporting you to nearby Città della Pieve where you’ll a private walking tour along its medieval alleyways. You’ll visit the centuries-old duomo – with its ancient catacombs, medieval foundations and unique, frescoed interior – as well as some of the town’s fabulous, winding avenues – including the narrowest alleyway in Italy! Last stop is our friend, Alessandro’s, saffron shop to enjoy an oh-so-fun saffron tasting and light lunch, featuring delicious, homemade dishes.

Afterwards you’ll have some time to relax and refresh at the villa before we head out for a very special truffle hunt with our friend, Michele and his adorable truffle dog. We’ll be hunting the forest for precious white truffles, found specifically this time of year, so be sure to wear your more comfortable trekking shoes. Aperitivo follows, featuring crostini with truffles (of course!) before continuing to our friend Pino’s pizzeria in the nearby town of Chiusi to enjoy classic, Tuscan-style pizza. Delectable!

Day 5 ~ Thursday, June 2: Cività di Bagnoregio, Orvieto

  • Walking tour of Cività di Bagnoregio, Orvieto, pasta-making class
  • Breakfast and dinner

This morning after an early breakfast, you’ll be heading to one of Italy’s most treasured villages  – Cività di Bagnoregio. Be sure you’re wearing your comfortable walking shoes, as you’ll be walking the scenic footbridge that spans the valley, leading to the medieval arched entranceway and into the ancient village itself. Spectacular! After exploring the winding alleyways of Cività it’s on to the stunning town of Orvieto, with its Etruscan foundations that date back nearly 3,000 years. Here you can grab lunch on your own, shop along the charming avenues or pop in for a visit of the town’s magnificent 13th century cathedral.

Afterwards, we head back to the villa where you’ll have some time to relax before joining Lorenza for a lively pasta-making lesson. Get ready to learn how to make hand-rolled pici, and discover how Italians pair pasta with just the right sauce (practically an art form). Aperitivo follows, then a delicious dinner, featuring your hand-made pasta, of course.

Day 6 ~ Friday, June 3: San Casciano dei Bagni 

  • Walking tour San Casciano dei Bagni, archeological site, aperitivo and lunch Daniela’s
  • Breakfast, lunch and dinner

This morning after breakfast, 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 truly amazing, private visit of a newly discovered archeological site, featuring the remains of Roman baths and an ancient temple. After time to explore the nearby hot springs, and perhaps soak your feet in the mineral waters, 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, June 4: Departure

Our drivers will be transporting you this morning 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. Please note that although group transportation is only provided to/from the airport in Rome, some of our guests choose to extend their stay in Italy before and/or after the trip. After you’ve registered, we’re happy to provide contact information for our favorite hotels in Florence, Rome and Venice – as well as a link to book train tickets.
  • Private van service to/from all towns and sites included in the itinerary
  • All abundant breakfasts, featuring Italian pastries and cakes, organic yogurt, seasonal fruits, eggs and more – plus caffè, cappuccino and herbal teas.
  • All regionally inspired dinners with local wines 
  • Most lunches
  • Daily cooking activities
  • Daily countryside or village walks (walks, not hikes!)
  • Entrance fees
  • Guided tours
  • Pecorino cheese tasting
  • Wine pairings
  • Olive oil tasting
  • Bruschetta lesson
  • Saffron lesson and tasting
  • Archeological site
  • Truffle hunt
  • Pasta-making lesson
  • Herb lesson
  • Biscotti-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.