Tuscany Women's Trip


experiencing Tuscany with a friendly group of women travelers with a spirit of adventure – just like you. From hands-on cooking lessons to scenic walks to visits with locals, this trip includes in-depth cultural experiences, excursions to medieval hill towns, visits to historic sites, private artisan demonstrations, 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: 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 and its three medieval neighborhoods, followed by a classic Italian aperitivo and regionally-inspired dinner prepared by the talented Chef Vito.

DAY 2: Montepulciano

  • Highlights: Tour of Palazzo Grande, wine tasting and lunch in 15th century cantina, gelato in medieval village
  • Breakfast, Lunch, Dinner

This morning, after an abundant breakfast, it’s 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 surrounded by silvery olive groves and sweeping vineyards that produce the world renowned Vino Nobile di Montepulciano. Here you’ll enjoy a walking tour, shopping and exploring, before continuing to our friends’ 15th century cantina for a private wine tasting, along with a delicious, light lunch. Afterwards we continue to the nearby village of Monticchiello for a post-lunch passeggiata, and perhaps an artisan gelato!

This afternoon brings free time to relax or explore on your own before we gather together for aperitivo and a delicious, chef-prepared meal, featuring delectable regional dishes and local wine.

DAY 3: Città della Pieve

  • Highlights: Morning walking tour, stamping lesson, cooking class
  • Breakfast, Lunch, Dinner

This morning, after breakfast, you’ll step back in time as we visit some of Città della Pieve’s historic sites, including the 15th century duomo with 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 unique that you can take home with you. After lunch at our friends’ cozy cafe, you’ll have some free time to rest and recharge.

In the afternoon, we’ll meet up for a walk to our friend, Chef Cristian’s, bistrot (he’s closing his doors, just for us!) where you’ll take part in an invigorating cooking lesson featuring seasonal, organic foods, followed by dinner featuring your culinary creations.

DAY 4: Siena

  • Highlights: Guided tour in Siena, visit to Siena duomo and Piazza del Campo, bruschetta 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 a 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!

In the afternoon, it’s back to Città della Pieve where you’ll have time to relax and recharge, or perhaps enjoy a walk along the winding, medieval avenues. This evening we’ll be heading to our friends’ tucked-away trattoria for a fireside bruschetta-lesson featuring the family’s own exceptional local olive oil. Dinner will be cooked right here alle brace (over coals).

DAY 5: Chianciano Terme

  • Highlights: Visit to thermal spa, pizza night
  • Breakfast, Dinner

This morning, after breakfast, our drivers will transport you to the ancient town of Chianciano, known for centuries for its restorative, thermal springs. Here, you’re in for a treat, as we visit one of the town’s thermals spas, nestled in a beautiful, shady park, where you can enjoy a variety of luxurious treatments – including soaking in hot, mineral waters. You might also check out the nearby shops or take a walk through the park. Lunch is on your own, here in the spa’s cafe, or in the town itself.

In the afternoon it’s back to Città della Pieve where you can take part in an optional “medieval” walk. Then it’s off to a private home for sunset aperitivo followed by wood-fired pizza at our friends’ classic pizzeria.

DAY 6: San Casciano dei Bagni 

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

This morning, after breakfast, we’re off to the charming village of San Casciano dei Bagni, where you’ll enjoy a private tour of an archeological site (an ancient Etruscan and Rome sanctuary), and one of the most important discoveries in Italy in decades. After our extraordinary visit, we’ll make our way to our friend, Daniela’s, restaurant, nestled between the walls of the town’s castle, where you’ll enjoy an exceptional, chef-prepared lunch.

In the afternoon, it’s back to the villa for some time to rest, explore or shop on your own, followed by a private tour and aperitivo in a “secret” location. Afterwards you’ll enjoy a special, farewell dinner prepared by Chef Vito.

DAY 7: Departure 

Early morning departure for Rome Fiumicino Airport


  • 7 days/6 nights at Boutique Hotel Vannucci
  • All sleeping rooms with marble, ensuite baths – no single supplement fee
  • Private group transportation to/from Rome Fiumicino Airport on arrival and departure dates
  • Private ground transportation to/from all locations included in the itinerary
  • All abundant, buffet breakfasts, featuring made-to-order Italian coffee or tea
  • 3 lunches at hand-selected cafes and trattorie
  • All regionally inspired dinners, prepared with exceptional, seasonal foods and served with wines from local producers 
  • Activities and experiences to remember for a lifetime
  • Accompaniment by team Strada Toscana, along with exceptional locals
  • Entrance fees to all sites and museums
  • Private, guided walks and tours
  • Hands-on cooking lesson
  • Wine tasting and lunch in a 15th century winery
  • Shopping at unique, local stores
  • Olive oil tasting and bruschetta-making lesson
  • Visit to one of the region’s top thermal spas
  • Private tour of archeological site
  • Stamping class with local artist
  • 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.


  • 2023 – May 28 -June 3: SOLD OUT
  • 2024 – May 5-11: ON HOLD
  • 2024 – May 19-25: 8 SPACES
  • Trip Price
    • Trip Price $3,170 USD. Single Room – Single Bed w/Ensuite Bath
    • Trip Price $3,370 USD. Classic Room – Single Occupancy w/ Ensuite Bath
    • Trip Price $3,570 USD. Superior Room – Single Occupancy w/Ensuite Bath
    • Trip Price $3,170 USD per person. Superior Room – Double/Twin Occupancy w/Ensuite Bath
  • Select dates and room configuration upon booking
  • $700 deposit is required to book your space on this tour
  • No single supplement fee
  • Terms and Conditions