Tuscany Wine & Hike

Your guide will meet you this morning for a gorgeous hike that starts right from the hotel. We will cross the Arno River and climb to the magnificent Abbazia di San Miniato al Monte, where we will pause to explore this Romanesque jewel, which has stood here for 900 years. Our path winds through the quiet hills on the south side of the Arno, through the historic Pian di Giuliari district. Along the way, we pass elegant Renaissance villas and Galileo’s former observatory. Our hike ends at the Chalet Fontana, where we can enjoy a coffee before a 40-minute drive into the Chianti countryside for lunch at la Cantinetta di Rignana, a classic trattoria set amongst the rolling hills not far from Panzano in Chianti. After lunch, a 20-minute transfer to Fattoria Le Fonti, a beautiful small winery on the edge of Panzano in Chianti. Here we are welcomed by our friend Vicky, who owns and runs the winery. A brief visit to the winery is followed by a tasting of their Chianti Classico, Chianti Classico Riserva, and “super Tuscan” wines. If it is a nice day, the tasting will include a magnificent view over the vineyards and onto the distant Villa Vignamaggio, where Da Vinci painted the Mona Lisa. Afterward, a 20-minute drive brings us to Radda in Chianti, where we check into the 4-star Relais Fattoria Vignale. The hotel occupies a refined 17th/18th-century villa just outside the cobblestoned core of Radda in Chianti — a perfect mix of old-world charm and updated comfort. A two-minute walk into the village for dinner. The Hike: Very easy hiking on gently rolling terrain and on paved surfaces. Morning distance: 5.5 kms. Hike time. 1.5 hours plus time for explanations of the history. Overnight Radda in Chianti.  Transfer, winery visit and tasting, and dinner included. Lunch not included.

After breakfast, a private transfer brings us to the Castello di Brolio. Our morning hike begins beneath its towering ramparts and winds through vineyards and olive groves before climbing up to the castle itself, whose grey stone walls have watched over Chianti for nearly 900 years. We visit the park and gardens, as well as the small but engaging museum dedicated to Baron Bettino Ricasoli—Italy’s first Prime Minister and the man who defined the classic recipe for Chianti Classico. Lunch follows at a nearby trattoria, where local flavors take center stage. In the afternoon we stop at Ceramica Rampini’s workshop and store, a wonderful place to watch artisans create hand-painted majolica using traditional techniques. Their pieces blend Renaissance-inspired patterns with fresh, contemporary designs—beautiful dinnerware, jugs, and vases that make it hard to leave empty-handed. The Hike:  1 hour in the morning, relatively flat but sometimes rolling. Optional afternoon hike: 6 km (4 mi) loop over rolling, hilly terrain. Overnight Radda in Chianti.  Hotel, breakfast, and dinner included.

Our morning hike sets off right from the hotel and follows a beautiful route to Gaiole in Chianti. Along the way, we pass the stately Villa Vistarenni and the medieval, walled hamlet of Vertine—both postcard-perfect in their own ways. Lunch awaits in Gaiole at Trattoria Sfizio, a friendly spot known for hearty local cooking. Afterward, a short drive brings us to the tiny hamlet of Bricciano, where we meet Rory O’Kelly for a visit to his family’s cantina. Rory’s South African father founded this boutique winery in the 1990s, and Rory has carried that passion forward with real dedication. His goal is simple—make world-class wine—and the results absolutely speak for themselves. We’ll taste his white Sangiovese, a Chianti Classico, a Riserva, and two expressive “Super Tuscan” wines, all paired with generous platters of cheese and charcuterie. A 20-minute van ride returns us to Radda in the late afternoon, with time to relax by the pool or explore the village shops. Dinner tonight is al fresco at Ristorante Le Panzanelle. The Hike:  1.5 hrs in the morning, 2.5 hrs in the afternoon through rolling terrain. Overnight Radda in Chianti.  Hotel, breakfast, lunch, dinner, and tasting included.

This morning we enjoy a scenic 40-minute drive to Siena, one of Italy’s most beautiful and historic cities. We meet Rita, our favorite local guide, whose deep roots in this Gothic city make her the perfect person to explain the passion—and occasional fury—behind the famous bareback Palio horse race, run twice a year around the 12th-century Piazza del Campo. After the tour, you’ll have free time to wander the exquisite medieval center, admire the soaring Gothic architecture, or simply follow your nose to the tempting shops and cafés along Banchi di Sopra, Siena’s lively pedestrian street. Enjoy lunch wherever inspiration strikes, then we regroup for a scenic drive through the softly sculpted hills of the Crete Senesi on our way to the walled village of San Quirico d’Orcia. Our home for the next two nights is the charming four-star Villa Liberty. This evening, we stroll into the village for dinner at Trattoria al Vecchio Forno.  The Hike:  Urban hiking in Siena. Overnight in San Quirico .  Hotel, breakfast, and dinner included. Lunch not included

After breakfast, we have a short transfer towards Montalcino to begin our hike to the 13th-century Abbey of Sant’Antimo. The hike takes us through Brunello vineyards, verdant woods, and rustic farming villages before we arrive at the abbey. Sant’Antimo is one of the most important and famous examples of Romanesque architecture in Italy. After lunch at the trattoria in Castelnuovo dell’Abate, we have a short drive to “Uccelliera,” one of Brunello’s premier small wineries, for a truly unique and insightful tasting in their cantina. We start in the cellar and taste the still-unblended Sangiovese wines directly from the barrels of two different vineyards. Here we taste the difference that terroir, age, and even the type of oak barrel make to a wine. We then move to the tasting room to taste a flight of their Brunellos. On our way home, we will stop off in Pienza where you will have some free time to explore the town’s shops, cafés, and wine bars. Tonight we have a special dinner at Agriturismo La Fonte. The Hike:  2.5 hrs in the morning, through rolling terrain, mostly downhill. Overnight San Quirico d’Orcia. Breakfast, dinner, Brunello winery visit and tasting and hotel included.

Transfer to Arezzo train station for trains after 10:30 a.m. to Florence and Rome. Drive time is 1 hour. Transfer included.

Please note that some itinerary details may change depending on your tour's departure date. Whenever we run a tour, we make new discoveries. Sometimes they are good discoveries, like a wonderful new trattoria, and sometimes bad, like a trail has been washed away. Therefore, we sometimes change our itinerary to improve it by adding new, wonderful elements to the tour or removing elements that no longer work. Rest assured, we always aim to provide you with the best possible experience. We will advise you of any changes to the original itinerary before departure.