Tuscany Hill Towns

Walkers’ Tuscany Hill Towns

Best fully escorted, small-group walking tour of Tuscany by Strada Toscana! Just imagine…as the sun dips lower in the sky, you gaze out from ridge of a picturesque hilltop in Tuscany at sweeping views of the Val d’Chiana below. You’ve just explored evocative, ancient passageways, carved by Etruscans nearly 3,000 years ago and now you’re taking in a stunning, postcard-perfect scene – dipped in gold from the evening sun. In a few moments your private driver will transport you back to your luxurious accommodations to prepare for a relaxing aperitivo hour, followed by an exquisite gourmet meal.

TOUR DETAILS: Dates and Prices

  • 7 Days/6 Nights
  • Trip Price $4,295 USD per person, based on double occupancy, single supplement $595 USD
  • SINGLE SUPPLEMENT WAIVED through August 20th!
  • Dates:
    • May 20-26, 2018 – SOLD OUT
    • September 16-22, 2018 – SOLD OUT
    • September 23-29, 2018 – SPACES STILL AVAILABLE
    • October 21-27, 2018 – SOLD OUT

WALKING RATING: Our walks are rated as easy to moderate, with durations on average of 2-3 hours and distances of 5-10 kilometers (3-7 miles). Although most routes are relatively short, you will encounter cobblestones, rugged pathways, uneven steps and steep ascents and descents in order to reach stunning views and hilltop villages. Our walks ideal for active travelers. 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.


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. On that note, if our usual boutique hotels or B&Bs can’t accommodate us (which rarely happens), you can rest assured you’ll stay somewhere of an equal or higher level. The quality of our tours is never at risk, as our team is committed to excellence, along with our vast, local, Italian connections.

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REVIEWS : What People Are Saying

“Nothing but first class! From the accommodations, to the transportation, to the food… this tour was amazing. Pamela is a lovely hostess, friendly and upbeat.”Elizabeth St. Hilaire

“The trip of a lifetime! Every detail was perfect! Pamela is an expert, and everything was arranged beautifully. The day trips to local sights were amazing, she knows the best places, shops, and people. I can’t wait to arrange my next Italy experience with her.” Katheryn Kearny

DAY 1: Arrival

  • Mini-tour of accommodations and grounds, countryside walk, aperitivo hour and special welcome dinner
  • Dinner included

PLEASE NOTE: 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!

Benvenuto in Italia! Upon arrival at Florence Peretola Airport, sit back and relax as you are transported by our private Mercedes Benz van service to the Tuscan countryside and your elegant accommodations nestled in the heart of the scenic Val d’Orcia. After check-in, and a friendly welcome, you’ll have the opportunity to relax and settle in before enjoying a trip orientation and mini-tour of the grounds and accommodations with your Strada Toscana hosts and walking guide, Manuele de Bellis. Afterwards you’ll have an opportunity to walk on the nearby country lanes before getting together with your fellow travelers for a friendly aperitivo hour followed by a delicious, chef-catered welcome dinner.

DAY 2: Montepulciano & Monticchiello

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

MORNING: After breakfast you’ll join up with Manuele for a scenic walk to the village of Monticchiello, a medieval treasure that seems frozen in time. Then it’s off by private van service to Montepulciano 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: A light lunch will be served during our private wine tasting in our friends’ 15th century cantina (save room for gelato later!)

AFTERNOON: Enjoy time on your own for shopping (we’ll point out our favorite artisan shops), visiting churches or for wandering and grabbing a gelato before meeting up with Manuele to 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: Gather together with your fellow travelers at the villa for a friendly aperitivo hour, followed by a regional-style dinner at  award-winning La Grotta in Montepulciano.

DAY 3: Citta Della Pieve & Chiusi

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

MORNING: After a lovely buffet-style breakfast, you’ll travel to the border where Tuscany meets Umbria to walk a stunningly beautiful trail along a ridge that straddles the two regions. Then you’ll continue to the town itself where Manuele will guide you on along the medieval alleyways of Città della Pieve – including the narrowest streets in Italy – with a stop in a 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: We continue to the picturesque countryside near the historic town of Chiusi where you’ll enjoy some time on your own in the historic center of the village to 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: Aperitivo hour followed by dinner on your own in Montepulciano

DAY 4: : Sarteano & Val d’Orcia

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

MORNING: This morning after breakfast you’ll travel to the ancient Tuscan village of Sarteano, built upon a panoramic hilltop once inhabited by 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 panoramic park (weather permitting)

AFTERNOON: In afternoon 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 private 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: Aperitivo hour followed by dinner at our friends’ 5-star restaurant in Montefollonico

DAY 5: Torrita Di Siena

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

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 at the villa followed by dinner at our friends’ outstanding trattoria in Monticchiello

DAY 6: Pienza & Bagno Vignoni

  • Pienza ring walk, visit to thermal spa (optional/extra), private aperitivo concert
  • Breakfast and dinner included, lunch on your own

MORNING: After an abundant 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 and private concert at the villa  followed by a special chef-catered dinner featuring Tuscan specialities

DAY 7: Departure

Our drivers will transport you to Florence Peretola Airport

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SELECT ACCOMMODATIONS: VILLA POGGIO ALLE TRESE

Poggio alla Trese has been a part of a family estate since the 1600s – an estate that today includes stunning olive groves, sweeping vineyards and a precious little lake tucked into the nearby forest. The villa itself sits upon the very border of Tuscany and Umbria, an area that was prone to invasions by the Duke of Tuscany (back when feudal battles were the norm), and was lovingly restored in 2008. The renovation included updates and redos to the kitchens, bedrooms and bathrooms – all done with classy, traditional touches. The result is a villa that reflects its history with grace, and beckons to modern-day guests who love sumptuous sleeping rooms with characteristic touches.

INCLUSIONS Walkers’ Tuscany Hill Towns

  • 6 nights stay in at Villa Poggio alla Trese, near Chiusi (Tuscany)
  • 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, Manuele de Bellis
  • 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
  • 5 delectable dinners featuring regional specialties and accompanied by regional DOCG wines
  • Visit of Etruscan necropolis
  • Visit of medieval castle
  • Truffle hunt with local tartufaio
  • Private tour of Le Foce gardens
  • Private wine tasting in 15th century cantina
  • Private saffron lesson and tasting
  • Pasta-making lesson
  • Olive oil tasting
  • 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!

Not Included: Airfare, travel insurance, lunches, wine or other alcoholic drinks, inner-city bus, metro, train or boat transportation outside of those specifically listed in the trip package, tips 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 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. On that note, if our usual boutique hotels or B&Bs can’t accommodate us (which rarely happens), you can rest assured you’ll stay somewhere of an equal or higher level. The quality of our tours is never at risk, as our team is committed to excellence, along with our vast, local, Italian connections.

DETAILS: Walkers’ Tuscany Hill Towns

  • 7 Days/6 Nights
  •  Dates:
    • May 20-26, 2018
    • September 16-22, 2018
    • September 23-29, 2018
    • October 21-17, 2018
  • Trip Price $4,295 USD per person based on double occupancy
  • Single supplement $595 USD

DOWNLOAD ITINERARY

BOOK NOW

Have questions? Visit our Frequently Asked Questions Page

WHY CHOOSE a Strada Toscana Tour?

  • YOU’RE NOT JUST A NUMBER. We care deeply about our guests. In fact, we think of our small groups as a kind of family of like-minded travelers.
  • SMALL GROUP – BIG BENEFITS. Our maximum small-group size is 14, which means we’re able to stay in centrally located, boutique hotels (that often have limited rooms), eat in tucked away, family-run restaurants (that are always the best!) and use twin Mercedes Benz vans to reach restricted areas in historic villages.
  • WE’VE GOT YOUR BACK. Our support staff is always at hand to help you with everything from translating a menu to finding that special leather purse.
  • GORGEOUS & COMFY. You stay in upscale, boutique hotels with beautiful sleeping rooms, ensuite bathrooms and lovely touches that reflect the character of the region.
  • BEST VALUE. Because we’re destination experts and operate only in Italy, we know how to get the BEST quality for the very best price – that we then pass along to you. Our tours are an extraordinary value. Period.
  • YOU GET RIGHT TO IT. Spend less time transferring around in vans and more time experiencing. Your accommodations are in ideal locations for stepping outside to walk and explore.
  • PRIVATE DRIVERS. Strada Toscana teams up with exceptional drivers who own their own vans and their own businesses – and are really more like family. No conglomerates and no outside services.
  • AUTHENTICITY. Our trip leaders and guides are locals who are from the areas in which we tour. They know the region, the sites and the people like the back of their hand.
  • EXCEPTIONAL MEALS. The owner-run, top-notch restaurants on our tours are extraordinary, which means you enjoy delectable dinners in a welcoming, friendly atmosphere.

Learn more about our unique approach to traveling in Italy.