Tuscan Hilltowns Hiking

Tuscan Hilltowns Hiking

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Trip Length 7 Days
Group Size 4-14

Starting from


for REI Members

$4,499 for non-members


May 2019-Oct 2020

Indulge in natural beauty, romance and culture on a 7-day hiking adventure in Italy’s renowned Tuscan region.

Tuscany is an enticing place for romantics and adventurers from every corner of the world. Its enduring Renaissance culture, postcard-perfect countryside and warm sense of joie de vivre imbues everything from the cuisine to the people. With each day’s hike, we discover yet another quintessential landscape brimming with natural and historical beauty. This trip offers a chance to bear witness to the true character of Tuscany.

Gentle hills dotted with olive groves and poppy fields line our way to medieval hill towns. Our local guides use their expert knowledge of the area to paint a picture of Tuscany’s fascinating history. Stop at a small, family-run winery to taste exceptional Chianti and Vernaccia. Follow in the centuries-old footsteps of devout pilgrims as we walk along the Via Francigena. Marvel at Renaissance and Etruscan artifacts in world-class museums and galleries. Life moves at a leisurely pace on Siena's magnificent central piazza, "Il Campo"—a perfect place to relax over cappuccino and watch the world go by amidst new friends.

Trip highlights

  • Discover Tuscany's gorgeous landscapes, renowned wines, and warm people
  • Hike among charming, quaint hill towns, brimming with historical splendor
  • Enjoy fresh, authentic cuisine and taste regional wine
  • Walk through stunning landscapes of villages, olive groves, and poppy fields


This trip is rated Moderate [3]. The daily hikes range from 4-9 miles and are over varied terrain - from grassy lanes to rocky, gravel pathways.

Since some of the trails we hike can be steep and/or hilly, a conditioning regimen beginning at least 2-3 months prior to departure is highly recommended. Walking/hiking, running and biking are all great ways to physically prepare for this adventure. The better shape you are in, the more you'll be able to enjoy all that Tuscany has to offer!

  • Hiking

What's Included

Hotel accommodations with private bathrooms; meals as noted in the daily itinerary; guide/leadership; luggage transfers; private in-country transportation; special wine tasting; local city guides in Volterra and Siena.


Small hotels, 6 nights

Your Adventure Itinerary

Day 1

Meet in Florence and hike to the picturesque hill town of Volterra.

Our trip begins in Florence, Italy. The group will meet at a centrally-located hotel this morning, load luggage into the support vehicle and transfer to the outskirts of Volterra. We begin our first hike to this historic Tuscan town, situated on a plateau overlooking the surrounding countryside. Our walk takes us up through olive groves and vineyards, past stone farmhouses, and eventually to the imposing city walls. We have a light lunch in a local trattoria followed by a guided walking tour of Volterra, whose history spans Etruscan, Roman, Medieval and Renaissance periods. We visit the Etruscan Museum, where 3,000-year-old sculpted funerary urns, ceramics, and filigreed gold jewelry bear witness to the extraordinary sophistication of the Etruscan civilization. From atop the city's medieval walls we look down on the Roman Theater and out across the landscape of western Tuscany to the sea. On a clear day you can even see the islands of Elba and Corsica. The rest of the afternoon is free until we meet for an aperitivo and a brief orientation, followed by dinner. Overnight in Volterra for the next two nights. Lunch and dinner included.

Hiking: 4 miles; Terrain: Dirt and paved pathways; Elevation gain: 700'. Driving: 1.5 hours.

Day 2

Enjoy a quintessential country hike past olive groves and vineyards.

Following breakfast we transfer into the countryside to begin our walk through oak forests and vast wheat fields, surrounded by cypress trees and stone farmhouses. At the hamlet of Ulignano we stop for a picnic lunch at a farmhouse. Continuing our hike, we'll see Volterra's towers and steeples across the valley. After a van shuttle back to our hotel, the afternoon is free to explore Volterra or relax before dinner. Breakfast and dinner included.

Hiking: 7.5 mile; Terrain: Rolling hills; Elevation gain: 800'.

Day 3

Explore the exquisite medieval village of San Gimignano and enjoy lunch at the small Cesani family winery.

We transfer to Certaldo, to hike a route that affords us wonderful views of the "city of the towers," San Gimignano, and the imposing mass of the Villa Monte in the distance. We stop at Cesani, a small family-run winery which produces excellent Chianti and Vernaccia. A short tour is followed by a home-cooked lunch in which each course is paired with one of their wines. From here we transfer to San Gimignano to explore this exquisite medieval village. We finish the day in Colle di Val d'Elsa, an authentic Tuscan hilltown whose historic center still thrums with the rhythms of everyday life and is home to Italy's finest crystal makers. We spend the next two nights in Colle. All meals included.

Hiking: 7.5 miles; Terrain: Rolling hills with dirt and gravel pathways. Driving:1.5 hours.

Day 4

Hike near Colle di Val d'Elsa and enjoy lunch at a country residence.

A scenic loop walk from Colle takes brings us to a country residence set alongside the Via Francigena, which connects San Gimignano to Colle. We enjoy the wonderful views of the Tuscan hills and San Gimignano's distant towers while eating lunch on the terrace. Continuing on our hike we arrive back into Colle, with the afternoon free to peruse the crystal shops and a museum which highlights the centuries long tradition of crystal making in Colle di Val d'Elsa. Dinner is on your own, providing the opportunity to choose from a variety of authentic local trattorias and restaurants. Breakfast and lunch included.

Hiking: 9.5 miles; Terrain: Rolling hills with dirt and paved pathways; Elevation gain: 500'.

Day 5

Explore Siena with a guided visit to the city's most notable sites.

We transfer to beautiful Siena, one of Italy's most enchanting cities. Conquered by the Medicis in 1559, Siena became a backwater, frozen in time, making it one of Europe's finest examples of a preserved Gothic city. The high concentration of buildings from the 12th–14th centuries makes Siena unique, and the main square, "Il Campo," is considered by many to be Italy's most beautiful piazza (the famous bareback "Palio" horserace is held in the square twice each year). Our local guide will explain the mayhem and passion associated with the race and then take us to visit the Duomo and its medieval treasures. You'll have the rest of the afternoon to explore Siena on your own. Wander through its sinuous medieval streets, discover hidden piazzas, or simply relax with a glass of wine before we transfer to our Tuscan villa hotel in the hilltop town of Radda in Chianti. We spend the next two nights in this historic and charming walled village. Breakfast and dinner included.

Guided walking tour: 2 hours.

Day 6

Hike in Chianti past ancient castles and renaissance villas.

Today's hike begins at the Villa San Donato in Perano, a magnificent 18th century villa that dominates the surrounding countryside. We visit the medieval walled hamlet of Vertine before continuing our hike through vineyards and olive groves and past stone farm houses and the 17th-century Villa Vistarenni. We stop for lunch at the Colle Bereto winery, enjoying expansive views over the famed Tuscan vineyards. We return to Radda in Chianti, where the remainder of the afternoon is free to swim in the pool, explore the town's medieval center, or rest. We enjoy a final dinner together to celebrate our time in Tuscany. All meals included.

Hiking: 7 miles; Terrain: Rolling hills with dirt and grass pathways and some rocky sections; Elevation gain/loss: 1,150'.​

Day 7

Share a final breakfast with your guides and fellow travelers.

The trip concludes with a group transfer to the Florence airport; we plan to arrive by 10:00 a.m. Depart for home this afternoon or continue your adventure in unforgettable Italy. Breakfast included.

Driving: 1 hour.

Tuscan Hilltowns Hiking Departures

Adventure Expert


I love the stop on this trip at a family-owned winery. After a morning hike we enjoy a home-cooked lunch of Tuscan dishes paired with delicious wines. Then we overnight in the quintessential Tuscan hilltown of Colle di Val d'Elsa.


The most amazing experience.. every day better than the last

Every day we all kept saying... "this is the most amazing way to experience Italy" We ate the most delicious food. We tried all kinds of wine and other traditional drinks. Every restaurant owner or chef treated us lik...

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