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 talented Chef Vito.

DAY 2: Pienza

  • Highlights: Excursion to Pienza, pecorino 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 free time to explore and shop on your own. Afterwards we’ll continue to Fattoria Cugusi, a local sheep farm that produces some of the best pecorino in Tuscany. Here you’ll enjoy a light lunch and delicious pecorino tasting, along with spectacular views of the Val d’Orcia.

In the afternoon we return to Città della Pieve where you’ll have some free time to explore and shop on your own. This evening we meet up for a short walk to our friend, Gianluca’s, family-owned trattoria for a delicious dinner featuring fresh catch straight from the Mediterranean.

DAY 3: Orvieto

  • Highlights: Saffron experience, excursion to Orvieto, pizza night
  • Breakfast, lunch, dinner

This morning after breakfast we’ll join up for a Renaissance walking tour in the village, including a peek inside several historic churches that house extraordinary medieval and Renaissance masterpieces. Afterwards, we’ll make our way to our friend, Alessandro’s, saffron shop for a private visit where you’ll learn about this fascinating spice, produced in Città della Pieve since medieval times, followed by a delicious saffron tasting and light lunch.

This afternoon we set out on an excursion to the town of Orvieto, situated on a spectacular bluff overlooking the Val d’Chiana. First stop is the magnificent duomo of Orvieto – one of the most beautiful in all of Italy – followed by a fascinating underground tour. Afterwards you’ll have the opportunity to explore Orvieto on your own, and perhaps shop in the many colorful, majolica ceramic shops. This evening we return to Città della Pieve, and to our friends’ wood-fired pizzeria for a delicious pizza dinner.

DAY 4: Città della Pieve

  • Highlights: Renaissance walking tour, cooking class, olive grove visit
  • Breakfast, lunch, aperitivo

This morning, after breakfast, you’ll step back in time as we explore some of Città della Pieve’s historic churches and alleyways, including the narrowest street in Italy! Afterwards we’re off to our friend, Cristian’s, cozy bistro for an invigorating cooking lesson that includes seasonal, organic foods, as well as a look back at the history of foods and cooking in the area. After a tour beneath Cristian’s private wine cantina, you’ll enjoy a classic, Italian-style lunch featuring your culinary creations, 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! Afterwards we gather together to walk to a nearby olive grove for a rustic-style, sunset aperitivo.

DAY 5: Environs 

  • Highlights: Truffle hunt, stamping lesson, wine tasting
  • Breakfast, lunch, light dinner

This morning, after breakfast, we’re off the nearby countryside where you’ll discover hidden churches, restored farmhouses and spectacular views. Our final stop is Luca’s, shady “campo” where you’ll meet a local truffle hunter and his talented truffle-hunting dog, and where you’ll participate in a lively and oh-so-fun hunt for local, black truffles. Afterwards we’ll enjoy a picnic lunch right here, under the beautiful oak trees, along with a tasting of fresh truffles.

This afternoon, after some free time to relax and recharge, we join our friend and artist, Gaetano, for a delightful stamping lesson that includes designing your own canvas bag – and some other surprises. Afterwards we return to Hotel Vannucci, where Nicola will take you on a special, private tour of the exceptional wine cantina, followed by an informal wine tasting featuring wines from local, small production wineries.

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 hilltop 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, 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 feature ensuite, marble bathrooms)
  • 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
  • 5 lunches at hand-selected cafes and trattorie
  • 5 regionally inspired dinners, prepared with exceptional, seasonal foods and served with wines from local producers 
  • Several evening aperitivi
  • Daily accompaniment by members of team Strada Toscana
  • Entrance fees to all sites and museums
  • Private, guided walks and tours
  • Hands-on cooking lesson
  • Wine tasting
  • Pecorino cheese tasting
  • Saffron tasting
  • Private tour of archeological site
  • Stamping class with local artist
  • Free time to explore and shop on your own

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:
    • May 3-9, 2025
    • June 1-7, 2025
  • Trip Price: $3,295 – $3,795 (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 separate tub and shower (for friends traveling together)
  • $700 deposit is required to book your space on this tour
  • No single supplement fee
  • Terms and Conditions