Walking and Cooking in Tuscany

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OPEN THE DOOR to an Insider Experience 

  • Dates: October 24-30, 2021
  • Trip Price $2,600 USD per person, single or double occupancy
  • 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!
  • Accompaniment by Pamela Haack, along with team Strada Toscana


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 ~ Saturday, October 24: 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 ~ Sunday, October 25: 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, sheeps’ milk yogurt, organic honeys and marmalades, seasonal fruits, hearty cereals and farm-fresh eggs 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 some 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 delightful tasting of pecorino cheeses – a specialty of the area.

In afternoon, we return to the villa for some free time followed by a walk through the estate’s olive grove with Paola. You’ll learn all about the growing of olives for pressing before enjoying an oh-so-fun olive oil tasting. Afterwards, we head outside to the bruschetteria where Paola will teach you the ins and outs of making true bruschetta over wood coals (while enjoying a local vino, of course). Afterwards you’ll learn from our friend, Alessandro, how Italians cook meats alle brace (over wood coals), before enjoying dinner together.

Day 3 ~ Monday, October 26: Pò Bandino and Ficulle

  • Coffee bar, walking tour of Ficulle, ceramic cookware demonstration with Fabio, ciambelline-making lesson
  • Breakfast, lunch and dinner

This morning after a light breakfast, we’re off to a local coffee bar to learn all about Italian coffees – and how to make the perfect cappuccino. After all, coffee is a passion amongst Italians! Plus you might want to sample a local pastry while you’re at it. Then we head out to the ancient town 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, including entrance to the town’s fabulously preserved crenellated tower and frescoed churches. Afterwards we’re off to meet up with talented Fabio for a delightful ceramics demonstration. You see, 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. Then we head to Fabio’s restored wine cantina for a very special lunch, cooked and served up in Ficulle’s “cotta”. What a treat!

After lunch it’s on to our friends’ organic produce farm where you’ll enjoy a tour of the amazing gardens where they cultivate a staggering variety of vegetables and fruits – including 60 varieties of tomatoes! Here you’ll be able choose some of their exceptional produce (chef Lorenza will be sending along her shopping list) before returning to the villa for a bit of rest and relaxation. Then it’s time to don an apron and enjoy a hands-on cooking experience with delightful Lorenza before gathering together for  apertivo. Dinner includes some of your own dishes made with local organic produce.

Day 4 ~ Tuesday, October 27: Città della Pieve & Chiusi

  • Organic wine cantina, wine tasting, walking tour Città della Pieve, saffron tasting, pizza making!
  • Breakfast, lunch and dinner

This morning after another delicious breakfast, we’re off for a walk along the countryside lane (optional) before heading out to take a tour of a local winery that specializes in natural and organic wines. The views from the vineyards here are stunning! After a light lunch, accompanied by a special, private wine tasting, it’s back to the villa for a bit of free time before we continue to nearby Città della Pieve for a delightful walking tour with local guide, Bianca, who knows all the best kept secrets of this unspoiled hill town and its fabulous medieval history. Learn about Renaissance artist, Perugino (teacher of Raffaello) and view some of his precious masterpieces, as you meander brick-paved alleyways – including the narrowest avenue in Italy.

Next we make our way to our friend, Alessandro’s saffron shop, where you’ll enjoy a fascinating saffron lesson, followed by a private saffron tasting with aperitivo – so surprising and fun! Afterwards, you’ll continue to the hill town Chiusi and Pino’s Pizzeria, where you’ll enjoy a hands-on pizza-making lesson with Pino himself. Of course dinner is right here featuring your own pizza.

Day 5 ~ Wednesday, October 28: Cività di Bagnoregio

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

After another delicious breakfast at the villa, we head to one of the most treasured villages in the region, 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 village itself. Spectacular! After exploring the winding alleyways and vicoli of Cività it’s on to the ancient city of Orvieto – its Etruscan foundations dating to nearby 3,000 years ago. Here you can grab lunch on your own, explore the avenues and museums or pop in for a visit of the town’s magnificent cathedral – dating to the 13th century.

Afterwards, we head back to the villa where you’ll have some time to relax before we gather together for an oh-so-fun 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, and then a special wine pairings dinner (featuring your hand-made pasta, of course) where sommelier, Paola, will teach you her best tips for pairing wines with just the right dishes.

Day 6 ~ Thursday, October 29: Montegiove 

  • Truffle hunt, private castle tour, estate wine tasting, herb lesson
  • Breakfast, lunch and dinner

This morning, after breakfast, you’ll be heading into the region of Umbria to meet the 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 we find some truffles! Afterwards, it’s back to the castle (which dates to the 1200s) to enjoy a private, guided tour of the castle and its wine cantina with Lorenzo himself, followed by a light lunch and wine tasting, featuring the estate’s excellent wines – along with fresh truffles from our truffle hunt. Delicious!

Afterwards lunch we head back to the villa where you’ll have some time to relax and refresh before enjoy a fascinating herb lesson with our own chef, Lorenza, who is nothing less than passionate about herbs and their multitude of health and wellness benefits. Get ready to take notes! Then it’s time for our final apertivo together with Paola, followed by a special farewell dinner prepared by Lorenza, featuring some of her favorite herb-based dishes.

Day 7 ~ Friday, October 30: 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
  • Ciambelline-making lesson
  • 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.

OPEN THE DOOR to an Insider Experience 

  • Dates: October 24-30, 2021
  • Trip Price $2,600 USD per person, single or double occupancy
  • $500 deposit is required to book your space on this tour
  • No added fees


Contact us at info@stradatoscana.com to get on the wait list, or choose different dates from our Tours Page.