Our trip begins in Florence, Italy. The group will meet at 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 hike 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 hiking 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 at the four-star hotel La Locanda for the next two nights. Hiking: 6 kms/4 miles; Elevation gain: 220 m/70 ft. Duration: 2 hrs Driving: 1.5 hours. Hotel, lunch and dinner included. Hiking: 

Following breakfast, we transfer into the countryside to begin our hike 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. Hiking: 12 kms/ 7.5 mile; Elevation gain: 270 m/ 800 ft.  Duration: 3 hrs Driving: 20 minutes each way. Hotel, breakfast and dinner included.

After breakfast a thirty-minute 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 in the four-star Palazzo San Lorenzo. Hiking:12 kms/ 7.5 miles Elevation gain: 260 m/ 780 ft. Duration: 3 hrs. Driving:thirty minutes each way. Hotel and all meals included.

A scenic loop hike 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. Hiking: Hiking: 15 kms/ 9.5 miles; Elevation gain: 155 m/ 500 ft. Duration: 4 hrs Hotel, breakfast and lunch included.

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 make 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 four-star Palazzo Leopoldo, a Tuscan villa hotel in the hilltop town of Radda in Chianti. We spend the next two nights in this historic and charming walled village. Hotel, breakfast and dinner included. Driving: 35 minutes in the morning, and 45 minutes in the afternoon.

Today's hike starts as you step out of the hotel. Exit Radda and you are soon amongst vineyards and olive groves. We pass the winery of Colle Berreto and climb up to a ridge line for views back on to Radda and over the surrounding countryside. The trail leads us along a cypress lined driveway to the magnificent Villa Vistarenni whose fanciful facade is a Chianti landmark. We have a break beneath the villas original 16th century walls before continuing on to the walled medieval hamlet of Vertine. We are rewarded with vast views over the undulating hills of Chianti from Vertine's perched vantage point. We have lunch at a charming osteria in the village of Gaiole in Chianti, famous for its Chianti wines but also as home to the "Eroica" bike race. After lunch we return to Radda in Chianti with a private shuttle, 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. Hiking: 11.5 kms/ 7 miles; Elevation gain: 360 m / 1,150 ft'.​ Duration: 3 hrs. Hotel, breakfast and dinner included.

After breakfast we shuttle everyone to the Florence train station, arriving around 11:00 am. From there you can easily catch trains for the rest of Italy. Travel time to both Rome and Milan is about 1 hour and forty minutes. Breakfast and one group transfer included.

Please note: Some details of the itinerary may change according to the departure date of your tour. Whenever we run a tour we make new discoveries. Sometimes they are good discoveries, like a wonderful new trattoria, and sometimes they are bad, like a trail has been washed away. The result is that we sometimes change our itinerary to improve it by adding new wonderful elements to the tour or by removing something that does not work anymore. Rest assured, our goal is to always provide you with the best possible experience. We will advise you of any changes to the original itinerary prior to departure.  

The hikes in Tuscany cover a variety of terrain, from trail to dirt road, with many rolling hills to climb or descend. We have designed the trip so that there is always some free time in the late afternoon so you can relax, read, or enjoy the towns where we stay. Breakfast is included every day, and dinners reflect the excellent traditional food of the region. Daily distance between 8 and 16 kms (5 to 10 miles).