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 pasta-making and creative stamping lessons to a private wine tasting, delicious cheese sampling and super-fun truffle hunt, 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: Pienza

  • Highlights: Walking tour Pienza, visit to organic mill, olive oil tasting
  • Breakfast, lunch, dinner

This morning, after breakfast, our drivers will transport you to the Renaissance hill town of Pienza, situated in one of the most photographed areas in Tuscany, where you’ll take a walk along the town’s “passeggiata” lane, with sweeping views of the Val d’Orcia. Once inside the historic center you’ll have some free time to explore and shop on your own. Afterwards we’ll continue to the nearby Mulino Val d’Orcia, an organic, ancient grains mill that produces exceptional flours, pastas and breads. Here you’ll enjoy delightful tour of the mill, followed by a delicious, organic lunch served in the mill’s restaurant.

In the afternoon we’ll return to Città della Pieve for some free time, followed by a visit to a nearby olive grove for a private extra virgin olive oil tasting. Dinner at a local, family-owned trattoria follows.

DAY 3: Fighine

  • Highlights: Maiolica ceramics lesson, Renaissance walking tour
  • Breakfast, lunch, dinner

This morning, after breakfast, we make our way to the picturesque hamlet of Fighine, with its romantic, winding avenues. Here you’ll enjoy a guided tour of the village with our friends, Grazia and Cesare, that includes a visit to the old wash house and 15th century church. Afterwards it’s off to Grazia ceramics workshop where you’ll learn the centuries-old art of designing and firing maiolica – plus you’ll design your own beautiful maiolica tile to take home, with Grazia’s expert guidance of course. Afterwards our hosts will prepare a home cooked lunch in their countryside home.

This afternoon after some time to rest and relax you can shop the local boutiques and shops, or perhaps explore on your own. Afterwards we head to our friends’ cafe for a delicious aperi-cena (aperitivo and light dinner).

DAY 4: Città della Pieve

  • Highlights: Village walk, pasta class, shopping, pizza night
  • Breakfast, lunch, dinner

This morning, after breakfast, you’ll step back in time as we explore some of Città della Pieve’s medieval avenues and alleyways, including the narrowest street in Italy! Then it’s off to our friend, Cristian’s, bistro for an invigorating pasta lesson that includes a delightful history lesson of traditional foods in Italy. After a private tour beneath Cristian’s wine cantina, you’ll enjoy a classic, Italian-style lunch featuring your hand-rolled pasta, of course.

This afternoon, after some free time, you’ll have the opportunity to explore and shop along the town’s charming main avenue. The local boutiques and organic products shops are fabulous! This evening we’ll gather together at a private home for aperitivo and pizza.

DAY 5: Montepulciano 

  • Highlights: Renaissance walk, stamping lesson, Vino Nobile wine tasting
  • Breakfast, dinner

This morning, after breakfast, we’ll visit a number of local churches where you’ll view fascinating ancient artifacts and Renaissance masterpieces. Afterwards we’ll be joined by a local artist for an oh-so-fun stamping lesson where you’ll design your own tote bag or tea towel. Lunch today is on your own.

In the afternoon we travel to 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 brief tour in Piazza Grande, followed by shopping and exploring on your own. Next stop is our friends’ wine cantina for a private wine tasting, along with a delicious, light dinner.

DAY 6: San Casciano dei Bagni 

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

This morning, after breakfast, we’re off to the village of San Casciano dei Bagni – a town built upon a hilltop teaming with hot springs – 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, with an archeologist, 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 Città della Pieve where you can rest, explore and do some final shopping on your own, followed by a special, farewell aperitivo and dinner cooked alle brace (over coals).

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
  • 4 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 pasta making lesson
  • Vino Nobile wine tasting
  • Shopping at unique, local stores
  • Maiolica ceramics class
  • 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.


  • Dates:
    • October 20-26, 2024 – SOLD OUT
  • Trip Price: $3,195 – $3,695 (choose room type upon booking)
  • 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 is required to book your space on this tour
  • No single supplement fee
  • Terms and Conditions