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, Montepulciano, Orvieto 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
  • 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
  • Wine tasting in a 15th century wine cantina
  • Pasta making class!
  • Visit to an archeological dig
  • Pizza night!
  • 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: Bagno Vignoni, Pienza 

  • Highlights: Visit to Bagno Vignoni, Pienza shopping and exploring, 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 –  and the picturesque village of Bagno Vignoni, perched on a scenic bluff that overlooks the valley below. Here you’ll enjoy a fascinating walking tour with our friend, Giulia, an exceptional local guide who knows this part of Tuscany inside and out, before continuing to the Renaissance town of Pienza. Giulia will get you acquainted with this gem of a town, and then you’ll have time on your own to explore the  alleyways and artisan shops. (Pienza is fabulous for shopping!) Lunch is on your own at any number of inviting trattorie.

In afternoon its back to San Casciano dei Bagni for some rest and relaxation before gathering together for a delectable olive oil and truffle tasting – served with bruschetta. Delicious! Dinner follows in Daniela’s chic restaurant, nestled beneath the walls of the town’s imposing castle.

DAY 3 ~ TUESDAY, APRIL 26: Fonteverde, San Casciano  

  • Highlights: Fonteverde Spa, museum and private visit to archeological site,
  • Breakfast, Lunch, Dinner

This morning after breakfast, it’s off to be pampered at elegant Fonteverde Resort, a luxurious, thermal spa where you’ll enjoy a soak in steaming pools of mineral-rich waters. The thermal springs of this area have been used for thousands of years for wellness and cures. After a relaxing morning, it’s time to enjoy a refreshing lunch.

Following some free time after lunch, we’ll gather together for an invigorating walk from the village to the valley below, where you’ll enjoy an incredible, private visit of a recently discovered archeological dig that has uncovered an important Roman temple, and a variety of astounding treasures. Afterwards, it’s time for a friendly aperitivo and delicious, regional-style dinner.

DAY 4 ~ WEDNESDAY, APRIL 27: Montepulciano 

  • Highlights: Visit to Montepulciano, wine tasting in 15th century cantina, pizza night
  • Breakfast, Lunch, Dinner

After breakfast this morning, it’s off to the town of Montepulciano where you’ll enjoy a walking tour with Giulia, as you get to know the layout and history of this beautiful Tuscan hill town, known worldwide for its exceptional wine – Vino Nobile di Montepulciano. Plus the views over the valley and vineyards are simply breathtaking! Your tour ends with a visit to a 15th century wine cantina, and a very special wine tasting and light lunch.

Afterwards you’ll have time to shop and explore on your own before our drivers transport you back to San Casciano. This evening you’ll enjoy aperitivo and dinner at one of our favorite pizzeria’s for a classic, Tuscan-style pizza.

DAY 5 ~ THURSDAY, APRIL 28: Orvieto

  • Highlights: Visit to Orvieto, tour of duomo, shopping
  • 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 enjoy the remainder of the afternoon on your own, before enjoying aperitivo and dinner at Daniela’s.

DAY 6 ~ FRIDAY, APRIL 29: Città della Pieve

  • Highlights: archeological site, walking tour Città della Pieve, pasta-making lesson
  • Breakfast, Lunch, Dinner

This morning, after breakfast, it’s off to the medieval village of Città della Pieve for a fascinating walking tour that includes a look inside the town’s cathedral, a viewing of a Renaissance masterpiece and a chance to explore the town’s fabulous, winding avenues – including the narrowest alleyway in Italy. You’ll also have time on your own to explore and shop. You don’t want to miss Francesca’s organic shop, Giovana’s fashion boutique or La Fema – an artisan shop that sells local gastronomic specialties.

Afterwards, it’s on to our friend, Lorenza’s restaurant, for an oh-so-fun lesson on how to make pici pasta, followed by lunch featuring (you guessed it), your hand-rolled pasta.

This evening we’ll gather together for a special farewell aperitivo and dinner, hosted by Daniela.

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 breakfasts
  • Most lunches
  • 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
  • Pasta-making lesson
  • Visit to archeological site
  • 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.