Tuscany Classic Chianti

Your guides will meet you in the hotel lobby of the Villa Agape 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 short scenic hike to the village of Panzano in Chianti, where we can enjoy a delicious gelato. Afterward, a 20-minute drive brings us to the Badia a Coltibuono, a 1,000-year-old monastery transformed into a warm and charming boutique hotel. 
Dinner tonight in the excellent Coltibuono restaurant. 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 15minutes. 
Overnight Badia Coltibuono. Breakfast, lunch, and dinner included. 

After a sumptuous breakfast, we set off on foot from the Badia and stroll into the village of Gaiole in Chianti. A cappuccino in the piazza fuels us for the next stretch, where the trail leads past the 10th-century Pieve di Spaltenna and winds through vineyards to Meleto Castle before looping back to Gaiole in Chianti where we have lunch at trattoria Lo Sfizio. In the afternoon, a short 15-minute transfer brings us to Brolio Castle where an easy walk takes us beneath its imposing walls and through its surrounding vineyards and olive groves before reaching the castle itself, whose stone ramparts have guarded these hills for nine centuries. We visit the park and gardens, and from the ramparts, the views seem to roll on forever. This evening we have a private dinner at Podere Ciona winery. The Hike: 10.4 kms /6mi Elevation gain: 265m / 850ft. Elevation loss: 390m / 1250ft. Duration: 3 hours. Afternoon hike: 5.8 kms /3.6 6mi Elevation gainand loss: 150 / 480ft. Duration: 1.5 hours. Overnight Badia Coltibuono. Hotel, breakfast, lunch and dinner included.

After breakfast, we set off on a short drive to the trailhead for a beautiful loop walk to the village of Volpaia. We pause in the piazza for a mid-morning cappuccino, then continue through a classic Tuscan patchwork of vineyards, olive groves, and cypress-lined paths. Lunch awaits at the charming Corte Domina winery, followed by a visit to Ceramica Rampini, where artisans hand-paint majolica ceramics using time-honored techniques. Their pieces blend Renaissance inspiration with fresh, modern designs—everything from dinnerware to jugs and vases. Those who wish can enjoy an optional late-afternoon walk back to Radda. Our home for the next two nights is the  Relais Fattoria Vignale, an 18th-century manor house turned elegant four-star hotel. Nestled on the southwest side of the hilltop village of Radda in Chianti, it offers sweeping views over the Chianti countryside. Dinner is just a two-minute stroll into the village. The Hike: 7 kms / 4.4 mi. Elevation gain and loss: 260m / 830ft. Duration: 2 hours. Optional afternoon hike:4.2 km / 2.6 mi. Elevation gain: 150m / 470 ft. Elevation loss: 130m/ 410ft. Overnight Radda in Chianti.  Hotel, breakfast, lunch, and dinner included. 

This morning’s hike begins in the quiet stone hamlet of Castello di Ama. Right on cue, we reach the little village of San Sano for a well-earned coffee before continuing our lovely loop walk. Along the way, we stop at the Church of San Giusto in Salcio, consecrated in the 11th century and still beautifully serene. Lunch in the piazza in Gaiole at Lo Sfizio. Afterward, a gentle one-hour loop leads us to Casa di Bricciano for a visit with winemaker Rory O’Kelly. His family’s tiny boutique cantina is one of the smallest in Chianti. Rory and his family are intent on making world-class wine, and the result is very persuasive. After the tasting, we return to Radda for some free time, or a loop hike from the village. The Hike:  7.2 kms / 4.5mi Elevation gain and loss: 200m / 640ft.  Duration: 2 hours. Afternoon hike: 4 kms /2.5mi Elevation gain and loss: 150m / 480ft. Duration 1 hour. Overnight Radda in Chianti at the four-star Relais Fattoria Vignale or similar. Hotel, breakfast, lunch, wine tasting, cooking class, and dinner included. 

Today, we have a scenic 40-minute van transfer to Siena, one of Italy’s most beautiful and historic cities. We have a guided visit with Rita, our favorite city guide. Only a native of this Gothic city can explain the furor and passion that surround the famous bareback Palio horse race, which is run around the city’s 12th-century Piazza del Campo twice a year. You will have free time to explore the exquisite historic center and admire its Gothic architecture. Of course, you might get sidetracked by the shops and cafés along the Banchi di Sopra, Siena’s main pedestrian shopping street. We have booked you for lunch at the Orto Dei Pecci, a wonderful local trattoria hidden away in one of the medieval orchards inside Siena’s city walls. After lunch we meet up for a scenic drive through the Crete Senese to San Quirico d’Orcia. Our hotel for the next two nights is the lovely four-star Hotel Capitano. You will be staying in restored 17th and 16th century village homes, in the heart centre of San Quirico. Tonight you will dine at the historic Trattoria al Vecchio Forno. The Hike: Urban hiking in Siena. Overnight: in San Quirico d’Orcia. Hotel, breakfast, and dinner included. Lunch not included. 

After breakfast, we depart San Quirico d’Orcia at 09:30 for the transfer to Chiusi-Chianciano Terme train station, arriving at about 10:30. Drive time is approximately 1 hour. For Florence, there is a direct 10:58 train that arrives at Florence Santa Maria Novella at 12:50. For Rome, the 10:54 train connects in Orte with a train arriving at Roma Termini at 13:00. There is also a direct 11:52 Intercity train that arrives at Roma Tiburtina at 13:27 (seat reservation required). Breakfast and 1 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 promising discoveries, like an excellent new trattoria, and sometimes they are bad, like a trail that has been washed away. Therefore, we sometimes adjust our itinerary to enhance it by adding new, outstanding elements to the tour or removing elements that are no longer effective. Rest assured, we always aim to provide you with the best possible experience. We will notify you of any changes to the original itinerary prior to departure.