Go off the beaten path and experience the essence of Tuscany up close! During daily walks, get away from the crowds to explore charming hilltowns, iconic landscapes, and impressive churches. Savor the region's bounty during special tastings and relaxed meals, and stay in delightful lodgings. 

Starting at: $5,495 Register Interest or Call 833-254-6678
 The landscape of Tuscany's Crete Senesi   Gathering for a special meal  The hill town of San Gimignano  The hill town of San Gimignano, featuring its many medieval towers  San Gimignano's historic square  Wine tasting in Tuscany  Enjoying the wine and food of Tuscany  Traditional cheese of Tuscany  Traditional foods of Italy  The hilltown of Monteriggioni  The Tuscan hill town of Volterra  Tuscan landscape with Siena on the horizon  The Campo, or main square, in Siena  Contrada flags in Siena  The facade and distinctive belltower of Siena's cathedral  Typical street in a Tuscan village  Taking a break over gelato  Tuscan landscape at dusk

Walks and Cuisine of Tuscany

9 days from $5,495

Go off the beaten path and experience the essence of Tuscany up close! During daily walks, get away from the crowds to explore charming hilltowns, iconic landscapes, and impressive churches. Savor the region's bounty during special tastings and relaxed meals, and stay in delightful lodgings. 

or Call 833-254-6678


Call Our Active Journeys Specialists at 833-254-6678 (M-F 10 am - 8 pm ET) or Register Your Interest Online. For calls outside of the U.S., please call 510-852-8350.


Hiking Tuscany’s iconic hill towns should be on every hiker’s life list. Join us for a unique walking tour featuring San Gimignano, Volterra, Monteriggioni, and Siena and the surrounding vineyards of Chianti, Vernaccia, and Brunello. During our daily routes you’ll explore churches, cathedrals, and abbeys, and of course, delight in tasting a variety of wines, cheeses, pressed oils, and local honey. And throughout your trip, savor meals comprised of local specialties and stay in hotels reflecting Tuscan charm. (Daily walks of 3 to 6 miles). 

Highlights Include:

  • Daily Hikes: Enjoy walks through Tuscany’s iconic landscapes and the hill towns of San Gimignano, Volterra, Monteriggioni, and Siena.
  • Tuscan Cuisine: Delight in the flavors of Tuscany during special tastings of wines, cheeses, pressed oils, and local honey, as well as meals featuring Tuscan specialties. 
  • Historic Accommodations: Return each day to upscale, historic castle hotels, situated either in the countryside or in the center of town.

To see itinerary, please click on an option below.


Day 1 — Depart the U.S.

Day 2 – Arrive in Florence, Italy / Gaiole in Chianti

Upon arrival, enjoy a light lunch then transfer to Gaiole in Chianti, one of the historical components of the League of Chianti. This afternoon, take a warm-up walk to the nearby village of Recine, then visit the Badia a Coltibuono, the “abbey of good harvest,” which was founded by the Vallombrosian monks about a thousand years ago. Vacated by the monks in 1810 and now privately owned, it is a sanctuary of peace and harmony where wine, olive oil, and honey are still produced today according to age-old traditions. A tasting of the local products will reveal why the estate of Coltibuono is so renowned.

Return to your hotel, originally a citadel, church, and monastery dating to 1030. Your castle hotel now offers upscale accommdations and amenities but is still replete with history and legend. This evening, enjoy a full immersion into the flavors of Tuscan cusine during dinner at the hotel's noted restaurant. Walking 2 hours. (L,D)

Day 3 — Gaiole in Chianti / Castello di Brolio

From the Romanesque church of Spaltenna, walk to the Castello di Brolio, home to the Ricasoli family since the 11th century. Here, you'll enjoy a visit to the garden and the panoramic view from the top of the castle walls. A highlight of your day will be a tour of the wine cellars where Chianti Classico originated, followed by a wine tasting. Hiking 3 hours. (B,L,D)

Day 4 — San Gimignano

This morning, enjoy a walk through more of the Chianti Classico countryside before transferring to San Gimignano, one of Italy's most picturesque and perfectly preserved medieval hill towns whose landmark towers emerge above the Tuscan countryside. Most people find it hard to resist taking a photo of the rectangular medieval towers for which the town is famous. The towers were more than defensive strongholds. In the incessant family feuds, they served as status symbols for both the families and the cities themselves, a visible measure of a town’s power and prosperity. You'll feel the history more strongly by staying overnight in a hotel that once welcomed pilgrims to this medieval village. Enjoy the hotel's central location, situated on the ancient main piazza, as well as panoramic views of the Tuscan countryside from the Terrace Restaurant.

In the afternoon, take a short walk in the hills surrounding San Gimignano and enjoy the landscape of cypresses, olive orchards, vineyards, simple churches, and stone farmhouses. The vineyards surrounding San Gimignano are well known for their prized white wine, Vernaccia. Roughly translated as “belonging here,” it is not surprising that records show Vernaccia grapes growing in the area since the 13th century. Walk along ridge tops with panoramic views of this beautifully cultivated region. Returning to San Gimignano, you'll have time to explore the cobblestone streets, piazzas, and restaurants, then enjoy dinner on your own. Hiking 3-4 hours. (B, L)

Day 5 — San Gimignano / Volterra

Today set out on a pleasant drive through the San Gimignano region in order to get close to Volterra, the most western of the ancient Etruscan Lucumonie. After a gourmet lunch in Palagione, visit the prestigious Etruscan Museum in Volterra. Volterra is also famous for alabaster, a soft stone found in the surrounding area. You'll stop to visit an important workshop, taking part in the carving of some alabaster objects. Return to San Gimignano for dinner. Hiking 3 hours. (B,L,D)

Day 6 — Colle Val d'Elsa / Monteriggioni / Siena

Depart on foot from San Gimignano and pass through olive orchards and vineyards en route to Colle Val d'Elsa, famous for its fine hand-crafted crystal. For 700 years, Colle has produced nearly all of Italy's best crystal, thanks to the area's forests which provided fuel for the glass furnaces and the rapid waters of the river Elsa which was used for the cooling process. Historic sites of interest point to the city's flourishing past during the Middle Ages and the Renaissance.

After a visit, continue your walk in the foothills and forests outside of MonteriggioniThe fields here are a patchwork of wheat and sunflowers, while the forests are a mix of chestnut, oak, and fir inhabited by deer and wild boar. Conclude your walk by ascending to the walled town of Monteriggioni. Built in the early 13th century as Siena’s northernmost bastion, it was often in the front lines in the wars with Florence. Now a neat circle of walls with 14 towers, it sits like a crown on its round hill. Later, transfer to Castello di Leonina, a historic hotel (originally a 13th-century fortress), situated outside Siena and featuring panoramic views of the landscape and delightful upscale amenities. Dinner is on your own this evening. Hiking 4 hours. (B,L)

Day 7 — Siena

Head into Siena this morning for a guided walking tour, visiting the major architectural and historical monuments, including the Piazza del Campo. The afternoon is free to explore the charming streets and museums of Siena on your own, do some shopping, or join your guides on a hike into the rolling, cypress-lined hills surrounding the town. Walking 3 hours. (B,D)

Day 8 — Val d'Orcia / Crete Senesi / Monte Oliveto

A fantastic drive through the Val d'Orcia showcases another iconic Tuscan landscape, the Crete Senesi. Solitary cypresses mark soft and round hills, following the run of the river Orcia. Your destination is Monte Oliveto Maggiore, a main Benedictine abbey, where you can see the beautiful frescoes by Sodoma and Signorelli, painters who tell the story of Saint Benedict through their work.

From Monte Oliveto, embark on a spectacular hike in the direction of Montalcino, the homeland of the Brunello wine. Time allowing, visit one of the wine producers for a final Brunello tasting. Join your fellow travelers for a farewell dinner. Hiking 4 hours. (B,L,D)

Day 9 — Depart for the U.S.

After breakfast, a transfer is provided to the Siena train station or Florence airport for departures. (B)

Included meals are denoted as follows: Breakfast (B), Lunch (L), Reception (R), Dinner (D)