Active Italy: Trekking & Tuscan Heritage - 7 Days

Day 1: Arrive in Florence, Tuscany's Renaissance Gem

Benvenuti in Firenze! Welcome to Florence, Tuscany's regional capital, famous for its glittering Renaissance art and architecture. Upon arrival at the airport, transfer to your city center hotel and settle in. Spend the day at leisure touring the top sights, starting in the Piazza del Duomo, where the magnificent Cattedrale di Santa Maria del Fiore (Il Duomo) and its mighty terracotta dome attract visitors worldwide. Don't miss the nearby Uffizi Gallery, which houses works by Leonardo da Vinci and Botticelli, and the Galleria dell'Academia, which displays Michelangelo's famous "David."

Stop for refreshments at one of the historic cafés that line the square of Piazza della Republica and continue on to Il Ponte Vecchio, a medieval stone bridge with an array of jewelry shops and beautiful views along the River Arno. In the evening, fuel up on delicious Tuscan fare in anticipation of tomorrow's hike. 

Day 2: Transfer to Radda in Chianti, the "Village of the Vineyards"

Treat yourself to a traditional Italian breakfast of un caffè (coffee) and a cornetto (croissant) this morning. Then, transfer to Radda in Chianti, a small, charming village on the border between the Arbia and Pesa valleys. Settle in at your accommodation, and then it's time to hit the trail. You'll see immediately why Radda is known as the "village of the vineyards" as you cross routes covered with beautiful vines and olive groves. Return in the afternoon and reward your efforts with a relaxing aperitivo in the square before heading out to dinner. 

Walking time: 4 to 5 hours

Day 3: Transfer to Panzano, Return Hike to Radda in Chianti via Volpaia

Today you'll travel to Panzano, a medieval village situated exactly halfway between Florence and Siena, whose castillo (castle) dates back to the 11th century. There's plenty to admire in this enchanting town, and it's worth a stroll of the cobbled streets before you hike back to Radda in Chinati. Roughly halfway through, you'll pass Volpaia, a tiny Tuscan gem, off the beaten path and a great place to stop for refreshments at the village's one and only bar. Refuel on platters of prosciutto with pecorino and miele (honey) and a glass of Chianti before continuing your hike back.

Walking time: 5 to 6 hours
Elevation gain: 1,642 feet (500 m) ascending, 1,476 feet (450 m) descending 

Day 4: Visit Siena, Transfer to San Quirico d'Orcia

Enjoy a leisurely breakfast and put your hiking boots to one side this morning as you transfer to Siena for a day of sightseeing. Your first stop should be the vast Piazza del Campo, regarded as one of Europe's greatest medieval squares and the site of the twice-yearly Palio di Siena horserace. Stroll the narrow cobbled streets until you reach the city's Duomo, a Romanesque-Gothic with an intricate marble floor and works by Bernini and Donatello.

Pause for lunch at a neighborhood trattoria, and when you're ready to, continue to San Quirico d'Orcia, your base for the next few nights. This delightful medieval town sits on a hilltop halfway between Pienza and Montalcino. Famous for its iconic Val d'Orcia countryside filled with cypress trees and known as an important stop on the Via Francigena pilgrimage route, the village's elegant wide streets, and medieval architecture are the perfect backdrop for aperitivo before settling in at your accommodation. 

Day 5: Trekking in the Val d'Orcia

After yesterday's rest day, enjoy a day of hiking in the UNESCO World-Heritage-listed Val D'Orcia. Filled with lush rolling hills, reams of vineyards, and cypress-lined winding strade bianche (white roads), it's breathtaking landscape to hike through. After a short climb, you'll be rewarded with a wonderful view of the valley and the silhouettes of Ripa d'Orcia and Monte Amiata (southern Tuscany's highest points) in the background. Descend through vineyards and pass through the town of Bagno Vignoni (a great spot to cool off in the town's Roman pool) as you head back to San Quirico.

Walking time: 4 to 5 hours
Elevation gain: 1,642 feet (500 m) ascending and descending

Day 6: Hike to Pienza, Return Transfer to San Quirico

Today's hike takes you to Pienza, known as the "ideal city of the Renaissance" thanks to the vision of Enea Silvio Piccolomini (later known as Pope Pius II), who had the money and influence to transform his birthplace into an elegant example of Renaissance architecture. Visit the town's main sites, including the Cathedral of Santa Maria Assunta, the Municipal Palace, and the Piccolomini Palace. 

After lunch, stroll through the Piazza Pio II and cool down with a spritz at one of the sought-after tables along the city walls, with stunning views of the surrounding Val d'Orcia. When you're ready, transfer to San Quirico and enjoy a relaxed evening at a neighborhood trattoria. 

Walking time: 3 to 4 hours
Elevation gain: 1,148 feet (350 m) ascending, (492 feet (150 m) descending

Day 7: Hike to Monticchiello & Montepulciano, Return Transfer to San Quirico, Depart

It's your last day hiking in Tuscany, and to round off your trip, you'll take a transfer to Pienza and hike through one of the region's most famous areas: a cypress-lined road that zigzags toward the fortified village of Monticchiello, perched high on a hill overlooking the valley. Take time to wander the town's winding streets, enclosed by medieval stone houses, and visit the sandstone church of Pieve dei Santi Leonardo e Cristoforo. Enjoy lunch at one of the town's excellent local restaurants, and refreshed and revived, it's time to hit the trail one last time.

Your hike ends in the famous town of Montepulciano, known for its fine wines, historic streets, and beautiful views. It's a wonderful place to stroll and see Tuscan life unfold, with plenty of cafés and bars to grab an espresso or a spritz. Walk up to the Piazza Grande at the top of the town and see the town's landmark architecture and impressive 17th-century Duomo. When you're ready, transfer back to San Quirico, where your Tuscan hiking adventure concludes. Safe travels!

Walking time: 4 to 5 hours
Elevation gain: 656 feet (200 m) ascending, 328 feet (100 m) descending

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