Tuscany Cultural Adventure


…scenic walks in medieval villages, hands-on cultural 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 delectable food and wine.


What You Can Expect…

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 15th century wine cantina to exploring an archeological site to hunting truffles in an Umbria forest, our local friends provide you with unprecedented access, while treating you like part of the family.


From delicate ravioli, stuffed with sheep’s milk ricotta and spinach, to peposo, slow-simmered in red wine and rosemary, our hand-selected menus include seasonal dishes that are made with the freshest local ingredients, and prepared with love. Each carefully crafted lunch or dinner is based on regional dishes made with fresh, locally-grown foods, and paired with wines from exceptional, small-production wineries.

THE ROAD Less Traveled

For more than 15 years we’ve been creating relationships with locals that allow us to take you along the road less traveled, to experience places and meet people who are off touristy routes. This means that your vacation in Italy is much more than that. It’s an authentic immersion into true Italian culture – including being based in an unspoiled medieval village.


  • 7 days/6 nights stay (see accommodations link next to available dates)
  • 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
  • All dinners
  • Most lunches
  • Daily walks in medieval villages or countryside sites
  • Pici pasta-making class
  • Wine tasting
  • Visit of active archeological site
  • Saffron tasting
  • Pizza night
  • 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.


Trip Itinerary

Day 1 ~ Arrival

  • Highlights: Welcome and trip orientation
  • Dinner

Benvenuti in Italia! Upon arrival at Rome Fiumicino Airport, sit back and relax as you are transported by our private drivers to your beautiful accommodations in the village of Città della Pieve – your home base for the fabulous days ahead! After check-in you’ll have the opportunity to explore your surroundings with your trip host, and learn some of the fascinating history of the area. Then it’s time to learn how to set up a classic Italian aperitivo, before sitting down for a delicious, regional-style dinner to kick off the tour.

Day 2 ~ Montepulciano, Montichiello

  • Highlights: Walking tour Montepulciano & Montichiello, wine tasting in 15th century cantina
  • Breakfast, lunch, dinner

This morning, after breakfast, we’re off to Montepulciano, one of Tuscany’s most regal hill towns, surrounded by vineyards that produce the world renowned Vino Nobile di Montepulciano. After a walking tour of the historic center, you’ll have time to explore (or shop!) on your own. Then we’ll meet up to walk to our friends’ 15th century wine cantina, where you’ll enjoy a special, private wine tasting, paired with a delicious lunch.

Afterwards, we continue to the picturesque hill town of Montichiello for stroll along the medieval avenues, and perhaps a stop for gelato.  In the afternoon you’ll have some time to relax before we head to our friends’ inviting trattoria for bruschetta, served with the exceptional local olive oil, followed by dinner cooked alle brace (over coals).

Day 3 ~ Città della Pieve

  • Highlights: Walk in historic center, pasta making lesson
  • Breakfast, lunch and dinner

This morning, after a delicious breakfast, we meet up to explore the historic center of Città della Pieve, including a look at some stunning Renaissance masterpieces. Afterwards, we continue to our friend, Cristian’s, bistro, where where you’ll learn to make Tuscany’s traditional pasta, paired with just the right sauce – plus you’ll get a peek inside Cristian’s amazing wine cantina. Lunch will be served afterwards, featuring your handmade pasta, of course.

After lunch we’ll continue our exploration of the medieval avenues, including a jaunt through Italy’s narrowest street. Afterwards, you’ll have time to relax and recharge before we enjoy another aperitivo and dinner together.

Day 4 ~ Ficulle

  • Walking tour of Ficulle, hand-made cookware demo with Fabio
  • 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 have a chance to rest and recharge, and perhaps enjoy a traditional passeggiata (stroll) before meeting our friend, Alessandro, for a special saffron tasting and aperi-cena (apertivo/dinner).

Day 5 ~ Monteleone, Città della Pieve

  • Highlights: Truffle hunt, pizza night
  • Breakfast, lunch and dinner

This morning, after a light breakfast and an early start, you’ll be heading to the medieval hill town of Monteleone. Here you’ll be walking a trail through a beautiful holm-oak and pine forest as you take part in an oh-so-fun truffle hunt with brothers Andrea and Michele – and their amazing truffle dogs. Afterwards we continue to the brothers’ charming cafe for a special truffle tasting and lunch – served with local olive oil and wine, of course.

In the afternoon you’ll enjoy some free time, followed by a visit to one of our favorite local bars for a classic aperitivo followed by pizza at a wood-fired pizzeria.

Day 6 ~ San Casciano dei Bagni 

  • Highlights: Visit to active archeological site
  • Breakfast, lunch, dinner

This morning, after breakfast, our drivers will transport us 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 we’ll meet up with our friend and archeologist, Ludovico, for a private visit of a newly discovered archeological site, featuring the remains of Roman sanctuary and ancient temple. Afterwards we continue to our friend, Daniela’s chic restaurant, nestled beneath the walls of the castle, for aperitivo and a delicious, Tuscan-style lunch.

This afternoon  you’ll enjoy some time on your own before heading to a private home for a special aperitivo, followed by a farewell dinner prepared by Chef Vito.

Day 7 ~ Departure

Early morning departure for Rome Fiumicino Airport

ACCOMMODATIONS Boutique Hotel Vannucci

Hotel Vannucci began as a project of Vittoria Spinola, daughter of King Vittorio Emanuele II, who fled Pisa (and an arranged marriage with her elderly husband) to start a new life with her lover in Città della Pieve. Here, she and her soon-to-be new husband, Paolo, built two villas that became luxurious holiday accommodations for wealthy Romans vacationing in the countryside. In 1903 one of the villas became Hotel Vannucci, and today it maintains the elegance and refinement of its inception, with luxurious sleeping rooms, marble bathrooms and inviting gardens. A stay here is truly special, nestled just outside the medieval walls of the historic, and unspoiled, village of Città della Pieve. 

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  • Dates:
    • October 1-7, 2023 –  SOLD OUT
  • Trip Price: $3,295 – $3,795 USD (based on room type/selection)
  • Room Descriptions:
    • Single: Single occupancy, single bed, private ensuite bathroom
    • Classic: Single occupancy, double bed, private ensuite bathroom with walk-in shower
    • Superior: Single occupancy, double bed, private ensuite bathroom with tub/shower combination
    • Deluxe: Double occupancy, double bed or two singles, private ensuite bathroom with tub and shower (specifically for couples or friends traveling together)
  • $700 Deposit, per person, is required to secure your space on this tour
  • Terms and Conditions