A favorite: Tuscan Hills & Cortona

Posted in Chianti, Tuscany and Umbria, Italy, Italy Popular Walks, Trips


  • Walk the lush rolling hills and meander in the Tuscan countryside
  • Discover medieval towns with their fortified walls and meandering streets.
  • Visit a living renaissance town overlooking the Val D’Orcia and landscapes made famous by 14th century painters.
  • Visit churches quietly hiding some remarkable art.
  • Sip a glass of world-class Brunello.
  • Savor traditional cuisine made with the freshest ingredients.
  • Luxuriate in signature accommodations.

To read about walking in Tuscany, click here.

Group Departure dates

Luxury and Signature Accommodations available

May 3,  2020
June 7, 2020
October 10, 2020

Personalized Departures

Use our concierge service to plan based on your dates of travel and preferred hotels. Choose your dates and let us do the rest. Any day of the week, any month of the year!

What makes our trips special? We do all the work. All you have to do is pack. You can join one of our groups or create your own. Our advertised prices are for group of 4 or more people traveling together. If you are a private group, prices are provided based upon request.

*Personalized departure date

Trip Length 6 days/5 nights
Start/Finish Florence/Chiusi
Walk Rating Easy to Moderate
Included All breakfasts,two lunches, two dinners, luggage transfers, two wine tastings and more.
Hotels Superior and Luxury chic hotels included in pricing.
Price starts at $3,750*
Single Supplement $550*
Custom Departures $100 booking fee per couple


*All prices in US dollars. Ask about customizing this trip for other departure dates.

Day 1 Florence/San Quirico/Montalcino

In the morning our guide will pick you up in Florence for a private transfer to Tuscany’s famed Val D’Orcia. We’ll drive through quintessential rolling hills and perfectly aligned vineyards, with views that will take your breath away. After a typical Tuscan lunch, begin an introductory walk through ancient Roman roads that pass through the Brunello vineyards for which the region is famous. There is time before our welcome dinner to relax and be calmed by nature’s beauty.

The walk: 3.1 miles; 5 kilometers
Accommodations Luxury: Hotel Palazzo del Capitano or equivalent (L, D)

Accommodations Signature: Castiglione del Bosco or equivalent (L,D)

Day 2 Montalcino/Sant’Antimo/Pienza

Tuscany is best known for its art, history, food and wine. Today has it all. We begin with a hearty Tuscan breakfast. Next, walk to the picture-perfect Sant’ Antimo for a visit to the Benedictine monastery. We’ll walk through cool forests and rolling hills covered in olive groves and vineyards. If we’re lucky, we will come across grazing chianine – white cattle weighing up to one ton. Sant’Antimo is a Romanesque Abbey that dates from the 12th century. The monks still chant at specified times. A picnic lunch will be included today as well as a tasting of the famed Brunello wines.

End the day in Pienza, a renaissance town. The current rendition of this town was built by decree of Pope Pius II. In contrast to the narrow alleyways of medieval towns, the Pienza’s design placed an emphasis on making the blue sky visible between buildings. During your two-night stay in the area you’ll have a chance to visit local cheese shops that specialize in pecorino – pungent cheese made from sheep’s milk, taste local wines, and dine on organic foods.. Mmmm! Our guide will help you choose a perfect dinner spot either in Pienza or in San Quirico.

The walk: 7 miles; 11 kilometers
Accommodations: Hotel Palazzo del Captitano or equivalent (B, PicL, wine tasting)

Accommodations Signature: Castiglione del Bosco or equivalent

Day 3 Bagno Vignoni/Radicafoni

Visit the spa town of Bagno Vignoni, known since Roman times for the curative powers of its hot springs. From here, we’ll take a walk along the Orca River, with views over the undulating hills of the Val D’Orcia. Noteworthy is the fortress of Rocca d’Orcia, brooding over its little village and visible from various points along the walk.

In the afternoon, we visit the town of Radicafoni, a fortified “city,” that was originally under the control of the Benedictine Abbey visited on day 2. You’ll see the castle of the Italian Robin Hood, Ghino di Tacco. Occupations since historic times have reshaped what was once a substantial conical hill into a flat-topped mesa.

The walk: 8 miles; 12 kilometers
Accommodations Signature: Castiglione del Bosco or equivalent (B, D)

Accommodations Luxury: Hotel Palazzo del Capitano or equivalent (B, D)

Day 4 Montichiello

A walk in the countryside takes you to the village of Montichiello. Afterwards, there is a car transfer to Montepulciano, known for its rich Sangiovese Vino Nobile. This day will include a walking tour of Montepulciano and a wine tasting. Transfer to Cortona. This hamlet is a great town for meandering on your own, discovering back alleys, and locally owned restaurants.

The walk: 10 miles; 16 kilometers
Accommodations Luxury: Cortei Dei Papi or equivalent (B, wine tasting)

Accommodations Signature: Villa di Piazzano or equivalent (B, wine tasting)

Day 5 Cortona

Our guide will take you on a walking tour of Cortona and the hills surrounding the town made famous by Frances Mayes in Under the Tuscan Sun. Visit the Etruscan museum. The Etrurians formed the basis of what we know today as Italian food and family culture. They bred the first chianine, white cattle weighing nearly one ton and famed for Fiorintine steak.Tonight you’ll share a farewell dinner in the company of your guide.

The walk: 8 to 10 miles; 12 to 14 kilometers

Accommodations Luxury: Cortei Dei Papi or equivalent (B, D)

Accommodations Signature: Villa di Piazzano or equivalent (B, D)

Day 6

There is time this morning for a short walk before breakfast. After breakfast, our guide will transfer you and your luggage to the Chiusi train station which provides easy access to points north and south within Italy. Transfers to Florence are possible upon request (additional fees apply). (B)

Cooking classes available upon request and priced by request.



NOT INCLUDED: Airfares, airport taxes, travel insurance (mandatory), pre and post trip arrangements, personal purchases, mini-bar services, alcohol unless specifically included. Evia can help you plan all these additional aspects with our travel partners at GAM-SPS Travel Inc.

B= breakfast included, L=lunch included, PicL=picnic lunch included, D=Dinner included
All bookings through Garth Allen Marksted Travel, Quebec Licensee.

* Personalized Departure Dates: All trips can be organized to suit your individual needs and preferred departure dates. Supplemental charges may apply. Cooking classes available upon request.

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