Tuscany Hill Towns ~ Cultural Walking Tour


  • Frothy cappuccino under a rose-covered pergola
  • Gentle Tuscan breezes through your open window
  • Winding lanes flanked by pointy cypress
  • Crusty bread drizzled with new olive oil
  • Dusty pathways through vineyards and olive groves
  • Your toes, dangling in the pool
  • Fields of impossibly red poppies
  • Warm breakfast pastries
  • Bubbles dancing in your glass of Prosecco
  • Sitting on stone steps under a warm sun. Eyes closed.
  • Dining with new friends, under the stars

Welcome to our Tuscany Hill Towns cultural walking tour, and your stay at Villa Poggio alla Trese. It’s the best of two worlds, really: a historic Italian villa, reserved exclusively for our group, along with luxurious services, including a private chef, private drivers and a private (and oh-so-delightful) walking guide.

From walks between irresistible hill towns (with locals waiting to welcome you like family) to private wine tastings in medieval cantinas, your guide knows tucked away places the tourists have never heard of – after all, Tuscany has been his family’s home for longer than anyone can remember. Evocative historic sites, meandering countryside strade, and medieval villages await you, and that’s just the beginning. Be prepared to experience Tuscany, and a bit of her sister region, Umbria, with all of your senses.

DATES & PRICES: 7 Days/6 Nights

  • 2018
    • September 23-29, 2018 (closes August 20th!)
  •  2019
    • May 19-25, 2019
  • SUMMER SALE through September 1, 2018:  Regular Trip Price: $4,295, SALE PRICE: $3,895! Save $400!!! Price is per person, based on double occupancy.
  • Single Supplement $695 USD solo traveler, single occupancy. SINGLE SUPPLEMENT WAIVED through September 1st, 2018!


WALKING RATING: Our walks ideal for active travelers and are rated as easy to moderate, with durations on average of 1.5 – 3 hours and distances of 5-10 kilometers (3-7 miles). Although most routes are relatively short, you’ll encounter cobblestones, rugged pathways, uneven steps and steep ascents and descents in order to reach stunning views and hilltop villages.  No hiking experience is necessary, but we do recommend walking regularly before your trip, including up hills, whenever you can. Although non-walking options are provided throughout the tour, we 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 others.


At Strada Toscana we weave amazing, authentic experiences into every trip, but sometimes unexpected things come up. If Mario calls to tell us they’re pressing olives at just this moment, off we go (I mean, you wouldn’t want to miss his newly pressed olive oil!), and if a site has an unscheduled closing, we improvise to include something equally as wonderful and interesting. You can rest assured that our plan Bs are really just extra plan As. 

Day 1: Arrival Poggio alla Trese

  • Welcome and trip orientation, vineyard walk, aperitivo, benvenuto dinner
  • Dinner

AFTERNOON: Meet up with the rest of your group in Florence at the Peretola Airport and journey together, via our private drivers, into the Tuscan countryside and your elegant accommodations, Poggio alla Trese. After some time to settle in, you’ll enjoy an invigorating walk along the nearby countryside lanes and through stunning, private vineyards.

EVENING: Tuscan-style apertivo followed by a delectable welcome dinner

Day 2: Montepulciano & Montichiello

  • Morning walk to Monticchiello, private wine tasting in our friends’ 15th century cantina, Montepulciano historic center, vineyard photo op, afternoon passeggiata
  • Breakfast, lunch and dinner

MORNING: After an delectable breakfast at the villa, featuring organic cheeses, fruits and freshly baked pastries, it’s off by private vans to Montepulciano and a scenic walk to the village of Monticchiello, a medieval treasure that seems frozen in time. Then it’s on to Montepulciano’s historic center, with its regal Renaissance palaces and spectacular views. You’ll begin your walking tour in the Piazza Grande before heading to our friends’ 15th century cantina for a private wine tasting and light lunch that includes world renowned Vino Nobile di Montepulciano and – one of Tuscany’s finest DOCG wines

LUNCH: In our friends’ 15th century wine cantina


  • Option 1: Enjoy time on your own for shopping (we’ll point out our favorite artisan shops), visiting churches or for wandering and grabbing a gelato
  • Option 2: Walk to the Renaissance church of San Biagio, just on the outskirts of town. Be sure to have your camera ready along the way, as the views of Montepulciano’s vineyards are out of this world!

EVENING: Poolside aperitivo hour at the villa, followed by a chef-prepared dinner  

Day 3: Città della Pieve and Chiusi

  • Hilltop scenic walk, medieval village walk, saffron lesson, archeological museum
  • Breakfast and dinner

MORNING: After an abundant breakfast at the villa, you’ll enjoy a panoramic walk along a stunningly beautiful ridge-line that straddles the regions of Tuscany and Umbria. Afterwards you’ll continue to the town of Città della Pieve for a delightful walking tour along the winding, medieval alleyways – including the narrowest street in Italy. We’ll also make a stop in a tiny, one-room museum to admire the stunning 15th century Adoration of the Magi, by Pietro Vanucci (Perugino). Then it’s on to meet our friend, Alessandro, a saffron expert, for a lesson and tasting of this remarkable local treasure.

LUNCH: Lunch is served up by our friend, Chef Cristian, who runs one of the most unique and inventive restaurants in Città della Pieve – proceeded by a toast in his 14 century wine cantina!

AFTERNOON: After lunch you’ll enjoy some free time at the villa to relax poolside or maybe under the shade of the old oak tree with a good book. 

LATE AFTERNOON: Our private drivers will transport you to the historic town of Chiusi where you can explore the excellent archeological museum (one of Italy’s finest!), visit the unique cathedral or photograph the surrounding Tuscan countryside from the town’s scenic park.

EVENING: Dinner at our friend, Pino’s, excellent pizzeria! 


Day 4: Sarteano and Val d’Orcia

  • Village walking tour, castle visit, walk to Etruscan necropolis, garden tour Villa Le Foce
  • Breakfast and dinner

MORNING: This morning after breakfast at the villa, you’ll travel to the ancient Tuscan village of Sarteano, built upon a panoramic hilltop once inhabited by the ancient Etruscans. In the historic center you’ll enjoy a walking tour that includes the town’s imposing medieval castle and tiny church of San Martino which houses the impressive 15th century Annunciation by Sienese artist Domenico Beccafumi. Simply stunning! You’ll then continue to nearby Necropli Delle Pianacce to visit this extraordinary, ancient tomb site with its sweeping views across the Val d’Chiana. Have your camera ready!

LUNCH: Picnic-style in the Park of the Pianacce

AFTERNOON: After some time to freshen up, back at the villa, it’s off to historic Villa Le Foce, a 15th century noble house restored and brought back to life by Iris Origo in the early 1900s. Here you’re in for the pleasure of a tour of the spectacular, manicured gardens overlooking the classic Tuscan landscape of winding cypress lanes, rolling wheat fields and stone farmhouses. A postcard brought to life!

EVENING: Wine pairings lesson in the villa’s hillside cantina, followed by a chef-prepared dinner under the stars

Day 5: Torrita di Siena

  • Forest walk with local truffle hunter (and truffle dogs!), walking tour of Torrita di Siena, pasta-making lesson, gelato-making demonstration
  • Breakfast, lunch and dinner

MORNING: After breakfast this morning, our drivers will be taking you to meet our friend, Michele, and his adorable truffle dogs, where you’ll walk an oak-shaded, winding pathway to test your luck at finding truffles. What fun! Afterwards you’ll continue on to the unspoiled medieval town of Torrita di Siena, where our friend and expert guide, Manuele, will escort you on a walking tour of his beloved home village. (Talk about insider access!) The tour ends in the small kitchen of the town “council” where you’ll take part in a delightful pasta-making lesson with women from the village..

LUNCH: Lunch is served in town hall and features your hand-made pasta – served up with truffle sauce, of course.

AFTERNOON: In afternoon it’s off to an artisan gelato shop where you’ll enjoy an oh-so-fun gelato-making demonstration, followed by gelato tasting, of course! Afterwards you’ll have some time on your own at the villa to relax, rewind or get in a few more steps on the nearby country lanes

EVENING: Aperitivo hour followed by dinner at the villa, featuring Umbrian dishes.

Day 6: Pienza and Bagno Vignoni 

  • Pienza ring walk, visit to thermal spa (optional/extra)
  • Breakfast and dinner

MORNING: After a delicious buffet breakfast at the villa, our drivers will be transporting you to the gorgeous Val d’Orcia and the charming hill town of Pienza – famous for its ideal Renaissance layout and its pecorino (sheep’s milk cheese). Here you’ll enjoy a picturesque ring walk with Manuele that features classic panoramic views that only the Val d’Orcia can offer. Afterwards you’ll have time on your town to explore your way through adorable Pienza with its many artisan shops and 15th century cathedral.

LUNCH: Lunch is on your own at any one of Pienza’s charming restaurants

AFTERNOON: We continue to the extraordinary village of Bagno Vignoni with its charming alleyways and centuries-old thermal pool – a picturesque jewel of the village. Here you can enjoy a walk along thermal springs to the natural pool outside on the outskirts of town, or opt instead for a visit to a thermal spa to soak in the luxurious, mineral-rich waters – a real treat!

EVENING: Aperitivo hour followed by a special, chef-prepared dinner featuring favorite Tuscan specialities

Day 7: Departure 

Transport to Florence Peretola Airport or Florence Santa Maria Novella Train Station.



EXTEND Your Vacation in Italy 

How about spending some time in Venice, Florence or Rome before or after your grand tour of Tuscany? We’re happy to help! Not only that, these are cities that you can easily explore on your own, and at your own pace, with just a bit of guidance. 

One you register for the Tuscany Hill Towns Cultural Walking Tour, we send along a complete itinerary that includes our complimentary, book-on-your-own, trip extension suggestions.  We share our favorite hotels in Venice, Florence and Rome, as well as how to arrange local guided tours. Need restaurant suggestions? We can help with that too. Or maybe you’d prefer to roam until you find a place that seems to be calling your name (highly recommended).

Oh, and let’s not forget about transportation. We share our suggestions about that too, so you know which options work best for you and your travel style.


  •  6 nights stay at elegant Villa Poggio alle Trese (The entire villa is reserved exclusively for our group!)
  • Private Mercedes Benz van service to/from Florence Peretola Airport upon arrival and departure
  • Private Mercedes Benz van service to/from all towns and sites included in the itinerary
  • Daily walks with expert Tuscany walking guide
  • All buffet-style breakfasts with a multitude of delicious choices, plus teas, juices and made-to-order Italian coffee
  • 4 delicious lunches featuring regional specialties and accompanied by regional wines
  • 7 delectable dinners featuring regional specialties and accompanied by regional wines
  • Visit of Etruscan necropolis
  • Visit of medieval castle
  • Truffle hunt with local tartufaio
  • Tour of Le Foce gardens
  • Private wine tasting in 15th century cantina
  • Private saffron lesson and tasting
  • Pasta-making lesson
  • Gelato-making demonstration
  • Entrances to cathedrals, museums and historic sites
  • Entrance fees to all sites included in trip itinerary
  • Daily accompaniment with a Strada Toscana team host or guide
  • Restaurant gratuities
  • Our small group guided walking tours offer daily options, including cultural experiences and tours for non-walkers. We always allow for flexibility, choice and spontaneity!
  • Daily guided walks, plus non-walking options: WALKING RATING: Easy to moderate, with durations on average of 1.5 – 3 hours and distances on average 5-10 kilometers (3-5 miles) – ideal for active travelers with or without hiking experience. You can expect hard cobblestones, uneven pavement, steps and steep hills. In addition, elevators are not available at our boutique hotel accommodations. Although non-walking options are provided throughout the tour, we 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 others.
  • Gratuities for hotels and meals

Not included: Airfare, ground or water transportation outside of that listed in the trip itinerary, alcoholic drinks, wines or meals ordered “on your own”, gratuities for 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 Mario calls to tell us they’re pressing olives at just this moment, off we go (I mean, we wouldn’t let you miss his newly pressed olive oil!), and if a site has an unscheduled closing, we improvise to include something equally as wonderful and interesting. The quality of our tours is never at risk, as our team is committed to excellence, along with our vast, local, Italian connections.