Tuscany Classic Chianti

Your guide will meet you this morning for a gorgeous hike that sets off right from the hotel. The trail 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, Galileo’s former observatory, and finally the magnificent Abbazia di San Miniato al Monte, where we pause to explore this Romanesque jewel that has stood here for 900 years. We return to Villa Agape before a 40-minute drive into the Chianti countryside for lunch at La Cantinetta di Rignana, a beloved trattoria tucked among rolling vineyards. Lunch on the terrace is features a vast view over the Tuscan hills. Afterwards, we transfer to the hilltop village of Montefioralle for a delightful two-hour loop walk. The day winds down at a small osteria overlooking terraced vines, the perfect spot for a cool drink before we settle in at 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 Hike: 7 kms / 4.4 mi. Elevation gain and loss: 260m / 830ft. Duration: 2 hours.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 toward Meleto Castle. From there, we continue up to the tiny hamlet of Castagnoli for lunch. In the afternoon, a short 20-minute transfer brings us to Brolio Castle. 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.  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 gain and 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. 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 /1.5mi 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 side-tracked by the shops and cafés along the Banchi di Sopra, Siena’s main pedestrian shopping street. Enjoy lunch in Siena and then meet up again before a scenic drive through the Crete Senese to Pienza. Our hotel for the next two nights is the lovely four-star Hotel Corsignano in Pienza, in the heart of the Val d’Orcia. The Hike: Urban hiking in Siena. Overnight in Pienza, San Quirico, or Montalcino.  Hotel, breakfast, and dinner included. Lunch not included

We ease into the day with a relaxed start—plenty of time for a second cappuccino in the sunny main square before we set off on a gorgeous loop walk straight from our hotel. The trail leads us out of Pienza, under its ancient walls, and into the rolling Tuscan countryside. Our destination is the postcard-perfect Cappella della Madonna di Vitaleta, a tiny chapel set amid a wide-open view and graceful cypress trees. Just nearby, a beautifully restored farmhouse-turned-low-key osteria makes the perfect spot for a mid-morning pause. We loop back toward Pienza on a quiet dirt road, winding past wheat fields and weathered stone houses slowly crumbling into the landscape. The skyline ahead is crowned by Pienza’s elegant steeple, perched on a rocky ledge. Lunch is at La Terrazza della Val d’Orcia, where the view is as unforgettable as the food—sweeping green hills, dotted with olive groves and vineyards. The afternoon is yours to explore Pienza, a UNESCO World Heritage site transformed by Pope Pius II into a Renaissance gem. Stroll its graceful streets, visit artisan shops, or simply sit back with a gelato or a glass of wine. Or, we can do an afternoon hike from Palazzo Maissani, a 16th-century fortified villa, to the medieval walled village of Monticchiello. We gather for our final dinner at La Fonte, a lovingly restored agriturismo just outside town. The Raggi family hosts us, beginning with a visit to their microbrewery and a tasting of Pienza’s famous pecorino. Dinner is served on the terrace—a warm, delicious end to a week of discovery and delight. The Hike: Morning: 8 km (5 mi), 250 m (800 ft) elevation gain. Duration: 2.5 hours. Optional afternoon: 7 kms/4.5 mi Elevation gain 210 m/670 ft Elevation loss: 170 m/550 ft. Duration: 2 hours. Hotel, breakfast, and dinner 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 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.