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

Starting at: $5,995 Register Interest or Call 833-254-6678
 The landscape of Tuscany's Crete Senesi   Gathering for a special meal  Vineyards and San Gimignano  San Gimignano's historic square  The hill town of San Gimignano  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  Evocative Tuscan landscape

Hikes and Cuisine of Tuscany

9 days from $5,995

Go off the beaten path and experience the essence of Tuscany up close! During daily hikes, get away from the crowds to explore charming hill towns, 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) to Book or to Learn More, or Register Your Interest / Ask Questions Online and we will reach out to schedule a convenient time to talk. For calls from outside of the U.S., please call 510-852-8350.


Celebrate Tuscany's timeless beauty and luscious culinary traditions during our hiking tour of this evocative region. Here, groves of silvery olive trees, swaths of vineyards, and rows of stately cypress are set amid a breathtaking landscape of gentle, undulating hills. Feel the warmth of the sun and the joy of hiking through the countryside and hill towns and discover the rhythms of Tuscan life, which still revolve around its agricultural and culinary heritage. Hikes are balanced with visits to historic and cultural sites as well as vineyards and wine cellars, farms, and other traditional culinary purveyors. (Daily hikes of 2 to 6 miles.) 

Highlights Include

  • Hiking and Culinary Highlights: Ascend to the imposing 13th-century walled hill town of Monteriggioni, with its circle of walls and 14 towers. Hiking to the 11th-century Castello di Brolio, home to the Ricasoli family, you’ll tour the wine cellars of prized Chianti Classico. Walk near Montalcino, home of Brunello, and along the ridgetops near the ancient fortified hill town of San Gimignano, surrounded by vineyards renowned for its Vernaccia. Along the way, sample a variety of wines, cheeses, pressed oils, and local honey where they are produced. Plus, savor Tuscan flavors during gourmet meals showcasing local specialties.
  • Historic Sites: Enjoy a tour of Siena’s Piazza del Campo and the distinctive black-and-white striped cathedral. View the interesting collection of Volterra’s Etruscan Museum and beautiful frescoes at the Benedictine abbey of Monte Oliveto Maggiore.
  • Lodgings: Another advantage of your small group is the opportunity to step back in time during stays in superbly appointed historic properties in the Tuscan countryside that reflect a well-preserved medieval reality.
  • Small-Group Feature: With a small group of no more than 18 people, you'll quickly develop a strong sense of camaraderie with your Adventure Guide and fellow active travelers—resulting in an interesting and enjoyable trip that is also more flexible! 


Day 1 — Depart the U.S.

Day 2 – Arrive in Florence, Italy / Badia a Coltibuono

Upon arrival in Florence, enjoy a light lunch then transfer to Gaiole in Chianti, one of the historical components of the League of Chianti. Visit Badia a Coltibuono, the “Abbey of good harvest,” which was founded by Vallombrosian monks about a thousand years ago. 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.

This afternoon, take a warm-up walk to a nearby village, then check into your hotel, a historic building that now offers upscale accommodations and amenities but is still replete with history and legend. This evening, enjoy a full immersion into the flavors of Tuscan cuisine during dinner at the hotel's noted restaurant. Hiking 2 hours. (L,D)

Day 3 — Gaiole in Chianti / Castello di Brolio

Begin the day by exploring the quiet streets of the charming village of Gaiole in Chianti. Today’s hike wanders the picturesque Tuscan countryside surrounding ​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

Enjoy a walk through more of the Chianti Classico countryside this morning, stopping for lunch in the charming village of Radda in Chianti.

After a delicious lunch of Tuscan dishes, transfer to San Gimignano, one of Italy's most picturesque and perfectly preserved medieval hill towns whose landmark towers emerge above the Tuscan countryside. The towers were more than defensive strongholds; they also served as status symbols for both the families and the cities themselves, a visible measure of a town’s power and prosperity.

Check into your peaceful hotel, a former Capuchin monastery located on the outskirts of town. This afternoon is free for you to explore the cobblestone streets, piazzas, and galleries of San Gimignano at your leisure before enjoying dinner on your own at one of the many charming restaurants in town. Hiking 2-3 hours. (B, L)

Day 5 — San Gimignano / Volterra

Today’s hike wanders through the pleasant wine-producing region to a lovingly restored villa. Appreciate the rediscovered frescoes and overgrown gardens.  Following a gourmet lunch in Palagione, visit the prestigious Etruscan Museum in Volterra to marvel at the impressive tomb carvings this somewhat mysterious civilization left behind. Volterra is also famous for alabaster, a soft stone found in the surrounding area that was especially important during the Renaissance. Duck into one of the many shops and studios that still specialize in this art today. Return to the hotel in time for dinner. Hiking 2-3 hours. (B,L,D)

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

Enjoy a short hike this morning around San Gimignano, and drive 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. Enjoy a short hike in the countryside surrounding this special place.

This afternoon’s hike follows the Via Francigena, the ancient pilgrimage path between Canterbury and Rome. Hiking through wooded hillsides of chestnut, oak, and fir, past churches that offered shelter along this sacred route, you will literally follow in the footsteps of countless pilgrims. Buon camino!

Next, visit 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 your lovely hotel, formerly an 18-century manor house, situated outside Siena and near Crete Senesi, and featuring panoramic views of the landscape and delightful upscale amenities. Hiking 3-4 hours. (B,L,D)

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 and the Duomo. The afternoon is free to explore the charming streets and museums of Siena on your own, do some shopping, or join your guides on an optional hike into the rolling, cypress-lined hills surrounding the town. Walking 3 hours. Optional hiking 2 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, round hills, following the run of the river Orcia. Embark on a spectacular hike in the direction of Montalcino, the homeland of Brunello wine.

This afternoon, visit the peaceful grounds of Monte Oliveto Maggiore, a Benedictine abbey, where you can see the beautiful frescoes by Sodoma and Signorelli, painters who tell the story of Saint Benedict through their work.

Return to our hotel this evening and gather for a festive farewell dinner, raising a glass of Brunello to toast your grand adventure. Hiking 3 hours. (B,L,D)

Day 9 — Depart for the U.S.

After breakfast, a transfer is provided to Florence airport for departures. (B)

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