Tuscany Cultural Adventure ~ Multiple Dates



scenic walks in the Italian countryside, delectable foodie experiences and insider access to private homes, vineyards and olive groves. This is a dream tour for those who love to explore and experience Italy as an insider. From the spectacular Val d’Orcia, with its breathtaking landscape, to the medieval hill towns of Tuscany’s wine country, get ready to immerse yourself in the traditions, culture, and spectacular scenery of the region – all while enjoying its delectable foods and wines. Plus this extraordinary tour also offers irresistible jaunts into nearby Umbria and Lazio, where you’ll discover the “fading” hamlet of Cività di Bagnoregio and the fabulous, winding avenues of Città della Pieve.


What You Can Expect…


There’s no better way to get to know a place, as an insider, than to explore, learn and converse with a local guide. Local guides live where they work, so they are a part of both the culture and the community. We partner with English-speaking guides that are not only licensed and local, but also hold degrees in history and art history – a must when visiting virtually any site in Italy, as art is simply everywhere. Plus our guides bring a heart-felt passion to their work. Put simply, they enjoy what they do, and can’t wait to share with you their knowledge, insight and love for their native land.

AUTHENTIC Experiences

Our Tuscany Cultural Adventure is an active trip for those who travel with a spirit of adventure. Each day includes tours, visits and hands-on activities that immerse you in Italian culture. From an exclusive wine tasting in a 13th century wine cantina to hunting truffles in an Umbria forest, our local friends provide you with unprecedented access, while treating you like part of the family. Of course this also means we leave some room for unscheduled events. If Mario calls to tell us they’re pressing olives, we make time to taste his freshly pressed oil!


From delicate ravioli, stuffed with sheep’s milk ricotta and spinach, to sea bass “al forno”, roasted under a bed of Mediterranean sea salt, our chef’s menus include seasonal Tuscan dishes that are made with the freshest local ingredients, and prepared with love. Each carefully crafted menu is based on regional dishes and seasonal, locally-grown foods. Plus our own sommelier pairs each meal with top-notch, regional wines.

EXCLUSIVE Accommodations

Your private accommodations are Poggio alle Trese, a 17th century villa nestled along the border of Tuscany and Umbria, and is reserved exclusively for our group, The villa boasts two kitchens, several lounge areas, dining hall, breakfast hall, sleeping rooms decorated with family antiques, swimming pool, outdoor terraces, 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 Tuscan hill town of Chiusi
  • Group transportation by private transport service to/from Rome Fiumicino Airport on arrival and departure dates
  • Private transport service to/from all towns and sites included in the itinerary
  • All breakfasts, featuring Tuscan breads and breakfast torte, organic yogurt, seasonal fruits, eggs and more – plus caffè, cappuccino and herbal teas.
  • All dinners, prepared by our private chef, that feature delectable Tuscan dishes served with regional wines 
  • Most lunches
  • Daily walks in medieval villages or countryside sites
  • Pici pasta-making class with our private chef
  • Vino Nobile wine tasting in 14th century cantina
  • Bruschetta-making lesson with olive oil tasting
  • Herb class with salty biscotti lesson
  • Visit to active archeological site
  • Saffron tasting
  • Free time 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.


  • October 16 – 22 – SOLD OUT
  • October 23-29 – SOLD OUT


  • May 21-27 – 2 SPACES
  • June 18-24 – 4 SPACES

Note: Select dates upon booking.


Trip Itinerary

Day 1 ~ Arrival

  • Highlights: 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 ~ Cività di Bagnoregio, Orvieto

  • Highlights: Footbridge to Cività di Bagnoregio, walking tour Orvieto, bruschetta lesson, olive oil tasting
  • 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 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.

In the afternoon, it’s back to the villa for some time to relax, or perhaps you’d prefer to stretch your legs on a walk, 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 authentic bruschetta (while enjoying some of the local vino, of course) followed by dinner cooked alle brace (over wood coals).

Day 3 ~ Pienza, Cetona

  • Highlights: Visit to UNESCO World Heritage sites of Pienza and the Val d’Orica, cantina visit and light dinner, gelato
  • 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 Pienza in the Val d’Orcia region of Tuscany – both are UNESCO World Heritage sites – and certainly the most photographed area in the region. With your private guide, who is also an art history expert, you’ll 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 browse the many artisan shops in the historic center of town.

Afterwards, it’s off to our friends’ historic wine cantina, in the charming town of Cetona where you’ll spend the evening “in famiglia” as you visit the centuries-old cantina and enjoy a wine tasting and light dinner, followed by a stroll through the historic piazza for gelato artigianale.

Day 4 ~ Ficulle

  • Walking tour of Ficulle, hand-made cookware demo with Fabio, 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 – including a climb up the fabulous, medieval town – before meeting up with our friend, Fabio, for 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”.

In the afternoon you’ll head back to the villa where you’ll have some time to relax and refresh before joining chef Lorenza for a salty biscotti lesson – the perfect savory biscuit to be served with aperitivo – followed by another delectable, regionally inspired dinner.

Day 5 ~ Monteleone, Città della Pieve

  • Highlights: Truffle hunt, walking tour Città della Pieve, 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 dogs. Afterwards, our drivers will transport you back up the hill to the brothers’ charming cafe for a special truffle tasting 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. Afterwards, you’ll have free time to shop and explore before heading to our favorite pizzeria for a dinner of wood-fired pizzas.

Day 6 ~ San Casciano dei Bagni 

  • Highlights: Visit to active 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. 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 aperitivo and farewell dinner, paired with top-shelf wines.

Day 7 ~ Departure

Early morning departure for Rome Fiumicino Airport


  • October 16 – 22 – SOLD OUT
  • October 23-29 – SOLD OUT


  • May 21-27 – 2 SPACES
  • June 18-24 – 4 SPACES

Note: Select dates upon booking.


  • Trip Price:
    • Single Occupancy with Ensuite Bathroom: $3,570 USD
    • Single Occupancy with Shared Bathroom (max 2 of same gender per bath): $3,270 USD
    • Double Occupancy with Ensuite Bathroom: $3,270 USD
  • $500 Deposit, per person, is required to secure your space on this tour
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