Tuscany Women's Trip - April 24-30, 2022


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 a private visit to an organic beauty-products shop (Francesca actually closes her doors, just for us) to a delectable wine tasting & lunch (hosted by sommelier, Paola) to a sumptuous visit to a thermal spa (the heated, mineral-rich pools are to die for!), 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.


Up-close, Super Fun and oh-so Authentic 

Upon your arrival, our private drivers will provide group pick-up at Rome Fiumicino Airport and transportation to the stunning Italian countryside and your chic accommodations in the picturesque village of San Casciano dei Bagni. After a warm welcome by your host, Daniela, and some time to get settled, you’ll enjoy a walking tour of the village followed by aperitivo and a delectable dinner prepared in the elegant dining hall, nestled beneath the walls of the town’s imposing castle.

Over the next amazing days you can look forward to…

  • Excursions to medieval hill towns like Pienza, Città della Pieve, Monticchiello, Sarteano and more…always with our private drivers and only with our own small group
  • Private, insider walking tours of historic centers with exceptional local guides who know the best local places to stop for a caffè or take in a stunning view
  • Hands-on pasta-making lesson and easy Italian cooking tips
  • Shopping at unique, local stores, like Francesca’s organic beauty products, Mario’s gastronomic specialties (think truffle cheese and Sicilian olives), Fabio & Giovana’s clothing boutique and soooo much more.
  • Olive oil and truffle tasting with bruschetta
  • Saffron tasting (a local specialty!) with our friends, Alessandro and Gianna
  • Tour of an Etruscan tomb site
  • Visit to a family-owned winery
  • Wine tasting with our own hospitality director, Paola – a sommelier, with a fun, fresh approach to tasting wines
  • Pasta making class!
  • Sunset aperitivo with your fellow, like-minded travelers
  • Visit to one of Italy’s top thermal spas, Fonteverde, with mineral rich, naturally heated pools that take the idea of relaxation up to the next level. Sit back and soak for a couple of hours, or indulge in a luxury massage.


DAY 1 ~ SUNDAY, APRIL 24: Arrival San Casciano dei Bagni

  • Highlights: arrival and welcome, walking tour of village
  • Dinner

Benvenuti in Italia! Upon arrival at Rome Fiumicino Airport, sit back and relax as you are transported by private van service to the Italian countryside and Sette Querce, your charming accommodations in the village of San Casciano. After check-in you’ll have the opportunity to explore your surroundings and learn some of the fascinating history of the both the structure and the area from owner, Daniela, a Tuscan native. This evening you’ll enjoy a classic Italian aperitivo, overlooking the rolling hills of Tuscany, followed by a special welcome dinner prepared by Daniela’s exceptional chef.

DAY 2 ~ MONDAY, APRIL 25: Pienza, Montichiello 

  • Highlights: Gladiator trail, Pienza shopping and exploring, walking in Montichiello, olive oil and truffle tasting
  • Breakfast, Dinner

After breakfast this morning, it’s off to the gorgeous Val d’Orcia, one of Tuscany’s most photographed areas. Here we’ll take a walk along a cypress-lined, dirt road where a famous scene from the Gladiator was filmed. So beautiful! Then it’s on to the town of Pienza – a Renaissance gem – for time on your own to explore the picturesque avenues or shop your way through town. Lunch is on your own at any one of the town’s inviting cafes or trattorie.

Afterwards we make our way to nearby Montichiello – a beautifully preserved hilltop village with stunning views of the Val d’Orcia below. Our stroll through the village ends at our favorite gelato shop 😁  before returning to your cozy accommodations in San Casciano. In late afternoon it’s time to gather together for a delectable olive oil and truffle tasting – served with bruschetta. Delicious! Aperitivo and dinner follow in Daniela’s chic restaurant, nestled beneath the walls of the town’s imposing castle.

DAY 3 ~ TUESDAY, APRIL 26: Sarteano, Fabro, Fonteverde 

  • Highlights: Etruscan site, Winery visit & tasting, Fonteverde spa
  • Breakfast, Lunch, Dinner

This morning, after breakfast, we begin a wonderful day of exploring and pampering. Since this part of Italy is the land of the ancient Etruscans and Romans, our first stop is an Etruscan tomb site that is both fascinating and stunningly beautiful, with its sweeping views over the Val di Chiana. Have your camera ready! Then it’s on to a family-owned vineyard for a stroll amidst the vines with Paola, followed by an easy-going wine tasting with light lunch in the cantina’s beautiful, stone tasting room.

In the afternoon, after some time to relax and refresh, it’s off for an afternoon of pampering at elegant Fonteverde, a luxurious, thermal spa where you’ll enjoy a soak in the sweeping pools of warm, mineral-rich waters. The thermal springs of this area have been used for thousands of years for wellness and cures. You might even book an extra treatment on your own, such as a massage or pedicure. This evening we’ll gather together for a friendly aperitivo, followed by dinner, at Daniela’s lovely restaurant.

DAY 4 ~ WEDNESDAY, APRIL 27: Città della Pieve

  • Highlights: Walking tour Città della Pieve, coffee bar, saffron tasting, shopping
  • Breakfast, Lunch, Dinner

This morning, after breakfast, our drivers will be taking you to the medieval village of Città della Pieve for a fascinating walking tour with local guide, Bianca, who knows all the best-kept secrets of this unspoiled hill town and its rich history. First stop is the centuries-old duomo, with its ancient catacombs, medieval foundations and unique, frescoed interior. After a pit stop at our friends’ coffee bar, you’ll wander with Bianca along some of Città della Pieve’s fabulous, winding avenues – including the narrowest alleyway in Italy – before taking some time to shop and explore on your own. Be sure not to miss Francesca’s organic shop, Giovana’s fashion boutique or La Fema – an artisan shop that sells exceptional local gastronomic specialties. Then it’s on to our friend, Alessandro’s, saffron shop for an oh-so-fun saffron tasting and light lunch – so surprising and fun!

After lunch you’ll make one final stop at a special, private location to take in the views before heading back to “home” to San Casciano. In afternoon you’ll have some free time to explore the village on our own, or even arrange a visit to Fonteverde spa for another soak in the thermal waters. This evening’s sunset aperitivo and dinner will be served up in Daniela’s elegant restaurant.

DAY 5 ~ THURSDAY, APRIL 28: San Casciano, San Litardo

  • Highlights: Village walk, Roman baths, vineyard lunch, pasta-making with Lorenza
  • Breakfast, Lunch, Dinner

This morning, after a leisurely breakfast, you’ll join our friend, Bianca – an exceptional local guide – for an insider tour of the village, followed by a walk into the countryside, where you’ll discover a beautiful park nestled amidst hot springs – including the remains of a Roman thermal bath that is still used by locals. After a tour of the many ancient pools, springs and fascinating archeological ruins, you’ll continue your walk to the family vineyard of Alessandro and his brother. Turn around and you’ll see a postcard view of San Casciano on the hill behind you. Lunch will be served up right here in the vineyard, including vino from these vines, of course.

In afternoon, after some time on your own to relax, you’ll be heading to our delightful friend, Lorenza’s, restaurant for a hands-on pasta-making lesson where you’ll learn all about regional pastas and how to pair pasta with just the right sauce. What fun! Afterwards you’ll enjoy an aperitivo with Lorenza, followed by and dinner, featuring your handmade pasta, of course.

DAY 6 ~ FRIDAY, APRIL 29: Orvieto

  • Highlights: Visit to Orvieto, tour of duomo, shopping, farewell dinner
  • Breakfast, Dinner

After breakfast this morning, it’s off to the town of Orvieto, perched on a dramatic bluff overlooking the valley below. First stop is the magnificent duomo with its 13th century marble facade and stunning frescoes by Renaissance painter, Signorelli. After a tour of the cathedral and main piazza, you’ll have the opportunity to explore on your own, or perhaps shop your way through the town’s winding avenues, lined with shops. Ceramics are a specialty here, and Orvieto’s archeological museums are exceptional. You might even opt for a fascinating underground tour! Lunch is on your own at any one of the town’s inviting cafes or trattorie.

Afterwards, it’s back to San Casciano where you’ll have time to rest up for this evening’s special aperitivo followed by a delectable farewell dinner prepared by Daniela’s chef.

DAY 7 ~ SATURDAY, APRIL 30: Departure 

This morning our private drivers will be transporting you to Rome Fiumicino Airport


  • 7 days/6 nights at chic Sette Querce Boutique Hotel, situated on the outskirts of the adorable medieval village of San Casciano dei Bagni
  • All single occupancy rooms with no single supplement fee
  • Group transportation by private van service to/from Rome Fiumicino Airport on arrival and departure dates
  • Daily, private ground transportation to/from all medieval hill towns, sites and locations included in the itinerary
  • All abundant breakfasts
  • All lunches with local specialties
  • All regionally inspired dinners with local wines 
  • Activities and experiences to remember for a lifetime
  • Accompaniment by Strada Toscana team members and exceptional local guides
  • Entrance fees to all included sites
  • Wine tasting
  • Olive oil and truffle tasting
  • Natural flower arranging lesson
  • Saffron tasting
  • Entrance to thermal spa and use of heated mineral pools
  • Evening aperitivo hour for chatting, sharing and relaxing

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

The Unexpected is Part of the Journey: At Strada Toscana we weave amazing, authentic experiences into every trip, but sometimes unexpected things come up. If a site has an unscheduled closing, we improvise to include something equally as wonderful and interesting. The quality of the trip is never at risk, as our team is committed to excellence, along with our vast, local, Italian connections.


Your accommodations are chic, boutique Hotel Sette Querce, nestled on the outskirts of the adorable medieval hill town of San Casciano dei Bagni, with its breathtaking views across Tuscany.

View the photo gallery.


  • April 24-30, 2022
  • Trip Price: $2,700 USD per person
  • $500 deposit is required to book your space on this tour
  • All sleeping rooms are single occupancy with private bathrooms
  • No single supplement fee
  • Maximum 8 participants
  • No hidden fees
  • Please see our FAQ page regarding Covid-19
  • Note: Should travel restrictions be issued by either the U.S. or Italian government due to the Covid-19 pandemic, any trip monies collected by us will be refunded in full, including your deposit. Otherwise, should you wish to cancel your participation in the trip, for any reason, our cancellation policy will apply.