Tuscany Walking, Cooking and Culture Private, Oct. 15-21, 2023

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OPEN THE DOOR to an Insider Experience 

  • Dates: October 15-21, 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 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, October 15: Arrival

  • Tour of Villa Poggio alla Trese, trip orientation, aperitivo lesson
  • 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, October 16: 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, October 17: Ficulle

  • Walking tour of Ficulle, hand-made cookware demo with Fabio, herb “walk” and salty biscotti lesson
  • 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, our drivers will transport you back up the hill 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 our friend’s saffron “house” where you’ll enjoy an aperitivo and saffron tasting – a surprising specialty of Città della Pieve. Afterwards, you’ll continue to one of our favorite pizzeria’s in the heart of town, for a dinner of pizza cooked in a wood-fired oven.

Day 4 ~ Wednesday, October 18: Città della Pieve

  • 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 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, October 19: Cività di Bagnoregio & Orvieto

  • Walking tour of Cività di Bagnoregio, Orvieto, pasta-making class
  • Breakfast, 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, in the historic center of town, you can grab lunch on your own, shop along the numerous charming avenues or pop in for a visit of the town’s magnificent 13th century cathedral.

Afterwards, you’ll head back to the villa for some time to relax and refresh 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, October 20: San Casciano dei Bagni 

  • Village and countryside walk, archeological site, apertivo and lunch at 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, October 21: 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 breakfasts
  • All regionally inspired dinners with local wines 
  • Most lunches
  • Daily cooking experiences
  • Daily countryside or village walks (walks, not hikes!)
  • Entrance fees
  • Guided tours
  • Wine tastings
  • Olive oil tasting
  • Tour of archeological site
  • Truffle hunt
  • Pasta-making lesson
  • Herb lesson
  • Pizza night
  • 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: October 15-21, 2023
  • Trip Price $2,950 per person
  • A $500 deposit is required to secure your space on the trip
  • 10 installment payments of $245 per month to commence September 2022