Tuscany Women's Trip, October 2-8, 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 elegant accommodations at Villa Poggio alle Trese. After a warm welcome with your Strada Toscana hosts, and some time to get settled, you’ll enjoy a walking tour of the grounds followed by aperitivo and a delectable dinner prepared by our own chef Lorenza.

Over the next amazing days you can look forward to…

  • Excursions to medieval hill towns like Pienza, Città della Pieve, Montichiello and more…always with our own private drivers and only with our small group
  • Private, insider walking tours of historic town centers with exceptional local guides who know the best local places to stop for a caffè or to take in a stunning view
  • Hands-on pasta-making lesson
  • Winery visit and wine tasting with our own hospitality director, Paola – a sommelier, with a fun, fresh approach to tasting wines
  • Shopping at unique, local stores, like Francesca’s organic beauty products, La Fema’s gastronomic specialties (think truffle cheese and Sicilian olives), Fabio and Giovana’s adorable boutique and more
  • Olive oil tasting and bruschetta-making lesson
  • Visit to organic flower farm
  • Saffron tasting (a local specialty) in our friend, Alessandro’s centuries-old cantina – such a treat!
  • Tour of an Etruscan tomb site
  • Visit to one of Italy’s top thermal spas, Fonteverde, with its 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 ~ Arrival Poggio alle Trese

  • Highlights: arrival and welcome
  • 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 Poggio alle Trese, your charming and historic accommodations for the next week. 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 your hosts. This evening you’ll enjoy a classic Italian aperitivo with your fellow travelers, followed by a special welcome dinner prepared by our own chef Lorenza.

DAY 2 ~ Puscina Flowers, Montichiello

  • Highlights: Organic flower farm, walk in Montichiello, olive oil tasting and bruschetta lesson
  • Breakfast, Lunch, Dinner

This morning you’re in for a treat, as our drivers transport you to our friends’ organic flower farm, situated in the heart of Tuscany’s wine country. Run by three sisters, and their creative mother, the farm boasts more than 500 varieties of flowers – all surrounded by picturesque, rolling vineyards. After a tour, and the opportunity to cut your own flowers, you’ll enjoy an easy-going lesson on natural floral arranging, followed by an organic lunch served up under an ancient olive tree.

After lunch, it’s on to the irresistible village of Montichiello, with its sweeping views over the valley below, for a scenic walk that ends at our favorite artigianale gelato shop. Then, back at your villa accommodations, you’ll have some time to relax and recharge before a taking part in a delectable olive oil tasting and bruschetta lesson, followed by aperitivo and dinner, featuring regional dishes.

DAY 3 ~ Sarteano, Fabro

  • Highlights: Walking tour of Sarteano tombs, Murogrosso wine tasting & lunch, pasta making
  • Breakfast, Lunch, Dinner

This morning, after another delicious breakfast, it’s time to begin a day of exploring and sipping! Since this part of Italy is the land of the ancient Etruscans, who occupied this region long before the Romans, our first stop is an ancient Etruscan tomb site that is both fascinating and stunningly beautiful. Next, you’ll make your way to a family-run winery, nestled in the Umbrian hills, with it’s sweeping vineyards of multiple varieties of grapes. After a tour through the vineyards with sommelier, Paola, it’s time for a laid-back wine tasting and light lunch, served up in the winery’s beautifully restored tasting room.

In afternoon we’ll head back to the villa where you’ll have some free time to rest or take an invigorating walk. Then in late afternoon it’s time to don an apron for a lively pasta-making lesson with Lorenza. Aperitivo and dinner follow, featuring your handmade pasta, of course!

DAY 4 ~ Città della Pieve

  • Highlights: Walking tour Città della Pieve, coffee bar, saffron tasting, shopping, aperitivo at a surprise location, pizza night
  • Breakfast, Lunch, Dinner

This morning, after breakfast, our drivers will be taking you to nearby 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 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 making your way to our friend, Alessandro’s, saffron shop to enjoy an oh-so-fun saffron tasting and light lunch – so surprising and fun!

After lunch it’s back “home” to relax for a bit, then in afternoon we return to Città della Pieve for shopping and exploring 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. Afterwards, we’ll meet up for aperitivo at a special, private location before continuing to Lorenza’s restaurant for pizza making and dinner. So fun!

DAY 5 ~ Pienza

  • Highlights: Gladiator trail, Pienza walking tour, shopping, lunch at Mulino, ciambelline lesson
  • Breakfast, Lunch, 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 a walking tour with your own private guide, followed by time on your own to explore the picturesque avenues or shop your way through town. For lunch we take a jaunt just outside of town to our friends’ organic flour mill, nestled in the walls of a former castle.

In afternoon, it’s back to the villa for time to relax, before learning to make ciambelline – a classic Italian biscotti – with Paola. Aperitivo follows, along with another delicious dinner prepared by Lorenza.

DAY 6 ~ San Casciano dei Bagni 

  • Highlights: Fonteverde spa, farewell dinner
  • Breakfast, Lunch, Dinner

This morning, after a light breakfast, it’s off to 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. Afterwards, a lovely lunch will be served up at our friend, Daniela’s, chic restaurant, nestled beneath the fortressed walls of the castle of San Casciano dei Bagni.

In afternoon, you’ll have time on your own to relax, take a dip in the pool or walk the countryside lane before gathering together with your fellow travelers for a special farewell aperitivo and dinner.

DAY 7 ~ Departure 

Early morning depart to Rome Fiumicino Airport


  • 7 days/6 nights at Villa Poggio alle Trese, situated on the outskirts of the town of Chiusi
  • All single occupancy rooms with no single supplement fee (note that some sleeping rooms share a bathroom – ideal when traveling with a friend!)
  • 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, featuring fresh-baked Tuscan pastries, organic sheep milk yogurt, local cheeses, seasonal fruits, organic cereals and fresh eggs, plus juices, herbal teas and Italian coffee
  • All lunches
  • All regionally inspired dinners with local wines 
  • Activities and experiences to remember for a lifetime
  • Accompaniment by team Strada Toscana, along with exceptional local guides
  • Entrance fees to all sites and museums
  • Village walks and tours with local, private guides (our group only)
  • Wine tastings
  • Olive oil tasting
  • Bruschetta making lesson
  • Saffron tasting
  • Shopping opportunities
  • Entrance to thermal spa and use of heated mineral pools – so luxurious!
  • 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 are elegant Poggio alle Trese, a 17th century villa, nestled along the border of Tuscany and Umbria, near the town of Chiusi (Tuscany). The villa boasts two kitchens, several lounge areas, dining hall, breakfast hall, sleeping rooms decorated with family antiques, swimming pool, outdoor patios, barbecue “house”, gazebo, wisteria-covered aperitivo terrace and so much more.

View the photo gallery.


  • October 2-8, 2022
  • 1 SPACE: Trip Price $2,650 USD. Single Occupancy with Shared Bathroom (max 2 per bathroom)
  • Terms and Conditions
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