Tuscany Women's Adventure


Exploring and experiencing Italy with a like-minded group of women, who have a spirit of adventure, just like you. From hands-on cooking lessons to scenic walks to visits with locals, get ready for an in-depth cultural experience that includes excursions to medieval hill towns, tours of spectacular historic sites, artisan demonstrations, private food and wine tastings and so much more.

OUR WOMEN’S TRIPS are Legendary 

Because we’ve been conducting them for years, so we’ve learned just the right balance of exploring, learning, cooking, experiencing and shopping that makes a women’s trip truly extraordinary. From super-fun cooking lessons and wine tastings to artisan shops and a luxurious, thermal spa, each experience is hand-selected and truly something special.

GET READY to Experience Real Italy

We’ve created this trip to be rich in experiences that are not only authentic, but also ideal for women who enjoy travel, fun activities, in-depth experiences, good food & wine and fellowship with like-minded travelers.

Each day, on this fabulously active itinerary, you can also expect to walk. Our walks range from easy/leisure to moderate, and you’ll encounter hard cobblestones, uneven pavement, steps and steep hills. We do caution that this trip is not the right fit for those who have difficulty walking or have a health-related condition that would limit participation and/or impede or inconvenience the rest of the group.


DAY 1 ~ SUNDAY: Arrival

  • Highlights: Arrival and welcome
  • Dinner

Benvenuti in Italia! Upon your arrival at Rome Fiumicino Airport, our private drivers will transport you to the Italian countryside, and your boutique hotel accommodations in the unspoiled village of Città della Pieve. After check in, you’ll enjoy a walking tour of the historic center of the village, with trip facilitator, Pamela Haack. This evening we’ll gather together with sommelier, Paola, for a classic Italian aperitivo, followed by a special welcome dinner prepared by Chef Vito.

DAY 2 ~ MONDAY: Montepulciano

  • Highlights: Walking tour in historic center, wine tasting and lunch in 15th century cantina, gelato in medieval village
  • Breakfast, Lunch, Dinner

This morning, after a delicious breakfast, we’re off to the gorgeous Val d’Orcia – one of Tuscany’s most photographed areas – and the picturesque town of Montepulciano, perched on a scenic hilltop overlooking vineyards and olive groves. Here you’ll enjoy a walking tour, plus time for shopping, before continuing to our friends’ 15th century cantina for a private wine tasting of Vino Nobile di Montepulciano, along with a light lunch. Afterwards we continue to the medieval village of Monticchiello – the ideal stop for artisanal gelato!

This afternoon brings free time to perhaps explore the village on your own before we gather together for aperitivo. Dinner follows at our friends’ cozy trattoria – just a few steps away.

DAY 3 ~ TUESDAY: Città della Pieve

  • Highlights: Morning walking tour, stamping lesson, pasta-making
  • Breakfast, Lunch, Dinner

This morning, after breakfast, you’ll step back in time as we visit the town’s 15th century duomo and view masterpieces by Renaissance artist, Perugino. Then it’s time to meet up with our friend and local artist, Gaetano, for an oh-so-fun stamping lesson – a centuries-old tradition, in Italy. With Gaetano’s expert guidance you’ll make something special and unique that you can take home with you. After a light lunch, at a local cafe, you’ll have some free time to rest and recharge.

In late afternoon, we meet up again for a short walk to our friend, Cristian’s, bistrot (he’s closing his doors, just for us!) where you’ll take part in an invigorating pasta-making lesson. Dinner follows, featuring your handmade pasta, of course.


  • Highlights: Guided tour in Siena, visit to Siena duomo and Piazza del Campo, salty biscotti lesson
  • Breakfast, Dinner

This morning, after breakfast, our drivers will be transporting you to the beautiful town of Siena, where you’ll meet up with delightful guide, Giulia, for an amazing walking tour of the historic city-center, including a visit inside the breathtaking duomo, a stop at the famous Piazza del Campo and an (optional) visit of the exceptional Museo Civico with its stunning frescoes.

Afterwards, you’ll have free time to explore on your own, shop and grab lunch at one of the many inviting restaurants. Giulia will be sure to recommend local specialties!

After returning to the hotel in the afternoon, you’ll enjoy some free time to rest and recharge before joining our friend, Lorenza, for a lesson on making salty biscotti – the ideal accompaniment to aperitivo. A delicious dinner follows, prepared by Chef Vito.

DAY 5 ~ THURSDAY: Chianciano Terme

  • Highlights: Visit to thermal spa, shopping, bruschetta-lesson, pizza night
  • Breakfast, Lunch, Dinner

This morning, after breakfast, our drivers will transport you to the ancient town of Chianciano for a leisurely, panoramic walk, overlooking the spectacular Val di Chiana. Then it’s off to an elegant thermal spa, where you’ll enjoy some time soaking in the naturally hot, mineral-rich waters. So luxurious! Lunch is here, on your own, in the spa’s cafe.

In the afternoon, we’ll return to Città della Pieve, where you can take part in an optional afternoon walk. Then we’ll head to a private home for an easy-going bruschetta lesson and aperitivo, followed by pizza at our friends’ inviting pizzeria.

DAY 6 ~ FRIDAY: San Casciano dei Bagni 

  • Highlights: Visit to archeological site, farewell aperitivo and dinner
  • Breakfast, Lunch, Dinner

This morning, after breakfast, we’re off to the charming village of San Casciano dei Bagni, famous since ancient Etruscan and Roman times for its mineral-rich hot springs. Here you’ll enjoy a special, private tour of an archeological site, with recently discovered Rome sanctuary – one of the most important discoveries in Italy in decades! Lunch follows, at our friend, Daniela’s, restaurant, nestled between the walls of the town’s castle.

In the afternoon, it’s back to the villa for some free time, followed by aperitivo and a farewell dinner prepared by Chef Vito.

DAY 7 ~ SATURDAY, JUNE 3: Departure 

Early morning departure for Rome Fiumicino Airport


  • 7 days/6 nights at Villa Poggio alle Trese, situated on the outskirts of the town of Chiusi
  • All single occupancy rooms with no single supplement fee (note that some sleeping rooms share a bathroom – ideal when traveling with a friend!)
  • Group transportation by private van service to/from Rome Fiumicino Airport on arrival and departure dates
  • Private ground transportation to/from all locations included in the itinerary
  • All breakfasts
  • Most lunches
  • All regionally inspired dinners with local wines 
  • Activities and experiences to remember for a lifetime
  • Accompaniment by team Strada Toscana, along with exceptional local guides
  • Entrance fees to all sites and museums
  • Village walks and tours with local, private guides (our group only)
  • Hands-on pasta-making lesson
  • Wine tasting and dinner in a 15th century winery
  • Shopping at unique, local stores
  • Olive oil tasting and bruschetta-making lesson
  • Visit to one of Italy’s top thermal spas
  • Private tour of archeological site
  • Salty biscotti-making class
  • Free time to explore and shop on your own
  • Evening aperitivo hour for chatting, sharing and relaxing with your fellow travelers

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

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.


  • May 28 -June 3, 2023 – SOLD OUT
  • Trip Price:
    • $3,170 USD per person: Single occupancy with ensuite bathroom
    • $2,970 USD per person: Double occupancy with ensuite bathroom
  • $500 deposit is required to book your space on this tour
  • No single supplement fee
  • Terms and Conditions