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 Piazza 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 brief tour in Piazza Grande, followed by shopping and exploring on your own. Next stop is 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!

After returning to Città della Pieve, and some time to relax and recharge, we take a fascinating Renaissance-inspired walking tour that includes a visit inside the town’s beautiful cathedral. This evening’s aperitivo is optional before we walk to our friends’ inviting trattoria for dinner cooked alle brace (over coals).

DAY 3: Città della Pieve

  • Highlights: Morning walking tour, cooking class, spa afternoon
  • Breakfast, lunch, aperitivo

This morning, after breakfast, you’ll step back in time as we explore some of Città della Pieve’s historic avenues, including the narrowest street in Italy! Afterwards we’re off to our friend, Cristian’s, cozy bistro for a tour of his private wine cantina, followed by an invigorating cooking lesson featuring seasonal, organic foods. A long, Italian-style lunch follows, featuring your culinary creations, of course.

This afternoon you’ll have time on your own to shop along the town’s charming main avenue or book a luxurious treatment at our boutique hotel’s onsite spa. This evening we’ll gather at a nearby cafe for aperi-cena (aperitivo and light dinner combined).

DAY 4: Siena

  • Highlights: Guided tour in Siena, visit to Siena duomo and Piazza del Campo
  • Breakfast, dinner

This morning, after an early breakfast, our drivers will be transporting you to the beautiful hill town of Siena where you’ll meet up with delightful local guide for a walking tour of the historic city-center, including a visit inside the breathtaking duomo and a stroll through the famous Piazza del Campo. Afterwards, you’ll have free time to explore, shop and grab lunch on your own at one of the many inviting restaurants.

In late afternoon, it’s back to Città della Pieve where you might enjoy a sunset walk along the winding, medieval avenues before we head to our friends’ exceptional restaurant for a typical, Tuscan-style dinner.

DAY 5: Citta della Pieve 

  • Highlights: Stamping lesson, shopping, special aperitivo
  • Breakfast, dinner

This morning, after breakfast, it’s time to get creative as we meet up with our friend and local artist, Gaetano, for a delightful mini-workshop where you’ll try your hand at ink stamping – a centuries-old tradition, in Italy. With Gaetano’s expert guidance you’ll make something unique that you can take home with you. Lunch today is on your own – of course we’ll have suggestions.

This afternoon we’ve set aside time for spa treatments at the onsite spa – or perhaps you’d prefer to get in a little shopping. This evening we’ll head to a private home for a special aperitivo, featuring the traditional Italian spritz, before continuing to a local pizzeria for wood-fired pizza. Afterwards, a stop at the local gelateria is highly recommended!

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 tiny 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, 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 or shop on your own, followed by a special, farewell aperitivo and 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
  • Visit to onsite Spa
  • 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:
    • May 19-25, 2024 – SOLD OUT
    • October 20-26, 2024 (8 spaces)
  • 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