Tuscany Wine & Hike

Your guides will meet you in the hotel lobby at 09:00 before we leave Florence for the Chianti countryside and our first hike. We begin at Passo Testalepre, following a cypress-lined ridge with sweeping vineyard views. After a short climb, the trail descends along an old Roman road toward the beautifully preserved hilltop village of Montefioralle. There’s time to wander its cobbled lanes and perhaps pause for a cappuccino before continuing through olive groves to the quiet hamlet of San Cresci, with its Romanesque church. Lunch is enjoyed at Locanda Poggio al Sole, where a vast view takes in the 14th-century Badia a Passignano. After a reviving lunch of pasta, local olive oil, and perhaps a glass of Chianti, we will be ready for a gorgeous but short hike 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. 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. Dinner is enjoyed at Casa Margherita, a three-minute walk from the hotel. The Morning Hike: 7 kms/4.4mi. Elevation gain and loss. 245m/785 ft. Moving time 2 hrs and 15 mins.  Afternoon hike to Panzano: 4.3 km / 2.7mi. Elevation gain: 100m /320 ft. Elevation loss: 80m/256ft Duration 1 hr and 15 minutes. Overnight Radda in Chianti.  Transfer, winery visit and tasting, and dinner included. Lunch not included.

After breakfast, we transfer to the village of Monti in Chianti for a lovely loop hike. The trail winds past old stone farmhouses and stately country villas, all under the watchful eye of Castello di Cacchiano. After our hike, a short hop brings us to Castello di Brolio, where we pause for a coffee or snack at the “Agribar” before strolling up to the castle’s impressive ramparts. Its grey walls have guarded Chianti for nearly nine centuries. We explore the grounds, gardens, and the small museum dedicated to Baron Bettino Ricasoli—Italy’s first Prime Minister and the man behind the historic formula for Chianti Classico. Lunch is arranged at a nearby trattoria in Castelnuovo Beradenga. An easy but very beautiful post-lunch walk helps us work off some of our pasta. On the way back to Radda, we visit Ceramica Rampini’s workshop and outlet. We will have a guided visit and learn how present-day artisans create hand-painted majolica ceramics using centuries-old techniques. Their work mixes Renaissance motifs with a modern touch—gorgeous plates, pitchers, and vases that are very hard to resist. Dinner this evening is at a small bistro run by the local butcher, just next door to his shop. We’ll enjoy a classic Tuscan ritual with the celebrated Bistecca alla Fiorentina (a vegetarian option is, of course, available). The Hike: Morning: Distance 5.2 kms/3.1 mi, Elevation gain and loss 105m/330ft. Moving time 1.5  hours. Afternoon. Distance 3 kms/1.9 mi, Elevation gain and loss 70m/220ft. Moving time 45 mins. Overnight Radda in Chianti.  Hotel, breakfast, and dinner included.

A five-minute drive brings us to the start of our morning hike, which 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 in the elegant hotel dining room. 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 Chiusi Chianciano Terme train station for trains after 10:30 a.m. to Florence and Rome. Drive time is approximately 45 minutes. There is a 10:54 train (one change) which arrives Rome Termini at 13:00 and a direct train departing 10:58 which arrives Florence at 12:50. 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.