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, 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, May 30: Pienza & the Val d’Orcia

  • Gladiator trail, walking tour of Pienza, sheep farm and pecorino lunch, olive grove walk, olive oil tasting & bruschetta-making lesson
  • Breakfast, lunch and dinner

This morning after a delicious breakfast featuring a variety of breads from the local pasticceria, organic yogurt, local honey, marmalades, seasonal fruits, hearty cereals and more, it’s off to the gorgeous Val d’Orcia, one of Tuscany’s most photographed areas. Here we’ll take a walk along a cypress-lined, dirt road where a famous scene from the Gladiator was filmed. So beautiful! Then it’s on to the town of Pienza – a Renaissance gem – for a walking tour with your own private guid, followed by time on your own to explore the picturesque avenues, tour the labyrinth of catacombs beneath the cathedral or shop 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 afternoon, it’s back to the villa for some free time followed by a walk through the estate’s olive grove, followed by an oh-so-fun olive oil tasting and bruschetta-making lesson. 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, ciambelline 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 private walking tour of the village with our friend, Bianca, an exceptional local guide, before meeting up with talented ceramist, Fabio, for a fascinating demonstration of his hand-thrown cookware. For centuries Ficulle was a center of hand-thrown 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 “cotta”.

After lunch it’s back to the villa for some time to relax, or perhaps you’d prefer to stretch your legs on one of several easy walking paths. Then it’s time to don an apron and try your hand at Paola’s grandmother’s recipe for ciambelline – classic Italian biscotti made with wine – before enjoying aperitivo together. Dinner, this evening, focuses on dishes made with local organic produce.

Day 4 ~ Wednesday, June 1: Città della Pieve

  • Walking tour Città della Pieve, coffee bar, saffron tasting, shopping, aperitivo in the piazza, pizza-making with Lorenza
  • Breakfast, lunch and dinner

This morning after another delicious breakfast, our drivers will be taking you to nearby Città della Pieve for a fascinating walking tour with 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 wander with Bianca 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!

Afterwards you’ll have some time to relax and refresh at the villa before rejoining Bianca in the historic center of town where you’ll learn about Renaissance artist, Perugino – born in Città della Pieve and a teacher of Raffaello. Viewing his precious masterpieces is such a thrill! Then you’ll have time on your own for shopping or exploring. Be sure not to miss Francesca’s organic shop, Fabio and Giovana’s fashion boutique or La Fema – an artisan shop that sells exceptional local gastronomic specialties. Afterwards, we’ll meet up for aperitivo in the town’s central piazza before continuing to Lorenza’s restaurant for pizza-making and dinner. So fun!

Day 5 ~ Thursday, June 2: Cività di Bagnoregio

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

This morning after breakfast we get an early start as you head 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 into the ancient village itself. Spectacular! After exploring the winding alleyways of Cività it’s on to the stunning town of Orvieto – its Etruscan foundations dating 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 a few kinds of pasta, but the star of the show is your hand-made tortellini. Plus you’ll 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: Montegiove 

  • Truffle hunt, tour of private castle, estate wine tasting, herb lesson
  • 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. Delicious!

After lunch it’s back to the villa where you’ll have time to relax and refresh before enjoy a fascinating herb lesson with Lorenza, who is nothing less than passionate about herbs and their multitude of health and wellness benefits. Get ready to take notes! Afterwards you’ll enjoy a special, farewell “aperi-cena”, with a delightful variety of dishes and 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 fresh-baked Tuscan pastries, organic sheeps’ milk yogurt, local cheeses, seasonal fruits, organic cereal, fresh eggs and cold cuts plus Italian 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
  • Wine tastings
  • Olive oil tasting
  • Private castle tour
  • Truffle hunt
  • Pasta-making lesson
  • Herb walk
  • Pizza-making
  • 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.


  • Dates: May 29 – June 4, 2022
  • Trip Price
    • $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
  • No added or hidden fees
  • Terms and Conditions
  • FAQs