Tuscany Classic Hike

After a hearty breakfast, we head into the idyllic Tuscan countryside to begin our day’s adventure. Our hike takes us through serene oak forests and golden wheat fields, framed by cypress-lined paths and timeless stone farmhouses. We pause for a picnic lunch in the charming hamlet of Ulignano. As we continue our journey, Volterra’s medieval towers and steeples punctuate the horizon. A quick van shuttle returns us to our hotel, leaving the afternoon free to enjoy Volterra at your own pace. Wander along the cobbled streets, stop to peruse the exquisite alabaster shops, or simply relax with a chilled drink in a sun-dappled piazza. In the evening, we gather for a memorable dinner at Ombra della Sera, one of Volterra’s most beloved trattorias. The Hike: 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 fantastic views of the "city of the towers," San Gimignano, and the imposing mass of the Villa Monte in the distance. We stop at Fattoria Cesani, a small family-run winery that 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 at the 4-star Palazzo San Lorenzo Hotel and Spa. The Hike: 12 kms/ 7.5 miles Elevation gain: 260 m/ 780 ft. Duration: 3 hrs. Driving: thirty minutes each way. Hotel and all meals included.

Today’s adventure takes us on a scenic loop hike from Colle, tracing the historic Via Francigena—the legendary pilgrimage route that has linked Canterbury to Rome for centuries. As you walk in the footsteps of ancient travelers, you’re treated to breathtaking views of Tuscany’s rolling hills and the iconic towers of San Gimignano in the distance. We pause for a leisurely lunch in the charming hamlet of Bibbiano, savoring local flavors before continuing our journey back to Colle. The afternoon is yours to enjoy as you wish. Wander through the enchanting maze of Colle’s stone-clad streets, unwind by the hotel’s outdoor pool, or indulge in some well-deserved relaxation at the spa. Dinner is on your own tonight, giving you the chance to explore Colle’s culinary gems. From cozy trattorias to the extraordinary two-Michelin-starred Ristorante Arnolfo. The Hike: 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 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 at the 4-star Hotel Palazzo Leopoldo & Spa.  Hotel, breakfast and dinner included.

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 onto 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 villa's original 16th-century walls before continuing 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 it's 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, you are free to enjoy the hotel spa,  explore the village’s medieval center, or sample some of the local wines from any one of the numerous ‘enotecca’ in Radda. We enjoy a final dinner together to celebrate our time in Tuscany. The Hike: 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 Montevarchi train station, where you can catch direct trains to both Florence and Rome. We arrive at the train station in time for 10:00 am trains. Travel time to Florence is 40 minutes to 1 hour, and to Rome it is 3 hours.  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.