Italy’s Tuscany Biking 6D5N (From Pienza To Siena & Chianti), Fully Guided

TWO BIKING OPTIONS:
Level 1, Approx. 26km (16 miles), 2-3 hours biking, Elevation gain: 274m (900 ft)
Level 2, Approx. 39km (24 miles), 2-4 hours biking, Elevation gain: 549m (1800 ft)

At 10:30 a.m., please meet your Trip Leaders at the main entrance of the Arezzo train station, located in Piazza della Repubblica. We ask that you arrive dressed in your biking clothes with your luggage and a daypack containing anything you might need for the day, such as rain gear and layers. Your main luggage will be taken to our first hotel.

Benvenuti in Toscana! From Arezzo, we will shuttle to a beautiful lunch spot overlooking the Val d'Orcia, a UNESCO World Heritage landscape, where we'll enjoy our first Tuscan meal together. Afterward, your trip leaders will provide a bike fitting and safety overview before you set off on a warm-up ride. You'll descend into a valley filled with chestnut groves, then pedal deeper into the Val d'Orcia before climbing out of the valley for sweeping views of rolling hills and iconic cypress-lined lanes. Our ride ends in the charming town of Bagno Vignoni, famous for its ancient thermal baths.

You’ll be staying at the charming Albergo Le Terme, located right on the main piazza, surrounded by the picturesque landscapes of Bagno Vignoni. Unwind and relax at its natural thermal spa facilities and wellness-focused amenities. This evening, we will gather for a welcome aperitivo, followed by dinner at the hotel.

FOUR BIKING OPTIONS:
Level 2, Approx. 29km (18 miles), 2-4 hours biking, Elevation gain: 457m (1500 ft)
Level 3, Approx. 55km (34 miles), 2-5 hours biking, Elevation gain: 762m (2500 ft)
Level 4, Approx. 76km (47 miles), 4-6 hours biking, Elevation gain: 1097m (3600 ft)
Level 5, Approx. 105km (65 miles), 5-7+ hours biking, Elevation gain: 1737m (5700 ft)

Today's journey begins in Bagno Vignoni, taking us through the idyllic countryside and storybook towns of the Val d'Orcia. Our route then climbs to Pienza, renowned as "the utopian city" for its remarkable Renaissance architecture. Take time to explore the city's heart, Piazza Pio II, and admire masterpieces like the duomo and Palazzo Piccolomini, designed by Florentine architect Bernardo Rossellino. You can linger over a coffee, browse the famed cheese shops, or continue onward for a more challenging ride.

For those seeking a greater challenge, three significant climbs lead to the village of Castelmuzio, set against a backdrop of Vino Nobile vineyards. Our path continues to Montepulciano, the highest of Tuscany's hill towns. After lunch, wander through its winding streets and hidden squares. We invite you to visit an enoteca near Piazza Grande to sample the celebrated Vino Nobile di Montepulciano. Just beyond the town walls, the Tempio di San Biagio offers another beautiful stop.

The return ride to Bagno Vignoni features more thrilling ascents and descents. You may choose to take a detour through Monticchiello, a medieval village offering sweeping vistas, or tackle the final climb to Campiglia d'Orcia before enjoying the exhilarating descent back to our hotel.

This evening, we will relax with a wine tasting and dinner in the heart of the Val d'Orcia.

FIVE BIKING OPTIONS:
Level 2, Approx. 22km (14 miles), 2-4 hours biking, Elevation gain: 580m (1900 ft)
Level 3, Approx. 43km (27 miles), 2-5 hours biking, Elevation gain: 800m (2600 ft)
Level 3, Approx. 60km (37 miles), 2-5 hours biking, Elevation gain: 1200m (3900 ft)
Level 4, Approx. 67km (42 miles), 4-6 hours biking, Elevation gain: 1300m (4200 ft)
Level 5, Approx. 82km (51 miles), 5-7+ hours biking, Elevation gain: 1600m (5300 ft)

Prepare to capture the beauty of southern Tuscany, as today's ride winds through its most picturesque landscapes. Leaving Albergo Le Terme, our journey takes us toward the acclaimed wine village of Montalcino, renowned for its world-famous Brunello di Montalcino vineyards. Here, you are invited to explore the town's quiet streets and admire its architectural treasures, including La Rocca, a restored 14th-century fortress, and the tower of San Martino, which offers expansive views over the Val d'Orcia. Afterward, visit a local enoteca to sample the region's prized Brunello wine.

Once back on your bike, you'll descend through a timeless landscape of olive groves and vineyards, passing the town of Buonconvento. A final climb brings you to an inviting agriturismo for a delicious Tuscan lunch. This afternoon, you may choose to shuttle to our next hotel or continue riding through cypress-lined lanes and fields of green and gold. The route offers a mix of challenging climbs and rewarding descents on the way to our home for the night, Borgo Casabianca.

You’ll stay at the rustic, Borgo Casabianca, an agricultural estate on a high ridge between the Chiana Valley and the famed Crete Senesi. Settle in and explore the grounds of this ancient village-turned-hotel, enjoy a refreshing swim at the pool, or take a walk to the nearby hamlet of Sinalunga. Tonight, we will gather at the estate to taste its award-winning organic olive oil before enjoying a Tuscan cookout.

FOUR BIKING OPTIONS:
Level 2, Approx. 40km (25 miles), 2-4 hours biking, Elevation gain: 520m (1700 ft)
Level 3, Approx. 43km (27 miles), 2-5 hours biking, Elevation gain: 580m (1900 ft)
Level 4, Approx. 58km (36 miles), 4-6 hours biking, Elevation gain: 790m (2600 ft)
Level 5, Approx. 84km (52 miles), 5-7+ hours biking, Elevation gain: 1190m (3900 ft)

Today's ride takes you into the Crete Senesi, a unique clay landscape known for its chalky, rolling hills—the biancane—which have been a source of inspiration for Florentine and Sienese artists since the 14th century. Your day begins with a gentle ride toward the quiet town of Asciano, passing pastures where sheep graze among historic stone farmhouses. From there, a steady climb leads you to the high point of the Crete Senesi, where you can pause to admire the view of Siena in the distance. The route continues over a series of rolling hills to the southern edge of the Chianti region. Here, we'll stop at a favourite agriturismo near Castelnuovo Berardenga for a hearty Tuscan lunch.

After lunch, we'll continue to our home for the next two nights, the Villa Curina Resort, a 16th-century villa nestled in Chianti's wooded hills with sweeping views of the countryside. Unwind at the serene Italian-style garden, a small church with frescoes by Arcangelo Salimbeni, or rejuvenate with a dip in the pool.

This evening, we will shuttle to Siena, a city celebrated for its medieval beauty and the historic Palio horse race. You will have the evening to explore and dine on your own in Siena; your leaders will be happy to recommend their favourite restaurants.

FOUR BIKING OPTIONS:
Level 2, Approx. 37km (23 miles), 2-4 hours biking, Elevation gain: 730m (2400 ft)
Level 3, Approx. 42km (26 miles), 2-5 hours biking, Elevation gain: 1000m (3300 ft)
Level 4, Approx. 64km (40 miles), 4-6 hours biking, Elevation gain: 1067m (3500 ft)
Level 5, Approx. 92km (57 miles), 5-7+ hours biking, Elevation gain: 1676m (5500 ft)

Today’s ride takes you through classic Tuscan scenery: vineyards, olive groves, oak forests, and rolling hills. Feeling up for a challenge? Try the Monteluco climb, a favourite among local cyclists. Prefer an easier pace? Follow the gentler route and stop at Ceramiche Rampini, a family-run ceramics workshop known for hand-painted Renaissance-style pieces—perfect for browsing or finding a unique souvenir.

The ride continues into the Chianti region, stopping in Radda, a charming town known for its role as the capital of the Chianti League in the 1400s and its production of Chianti Classico wine. Here, you’ll have time to explore, enjoy lunch on your own, and shop for keepsakes like a cycling jersey featuring the famous Gallo Nero (Black Rooster) logo.

After Radda, you can either take a shuttle back to the hotel for a relaxing afternoon or keep cycling for one last big ride. The route includes a downhill stretch through Sangiovese vineyards, traditional Tuscan buildings, and a final climb through the Chianti forest before returning to Villa Curina Resort.

Tonight, we’ll wrap up with a sunset aperitivo at the hotel and then head to a local restaurant for our farewell dinner.

Level 2, Approx. 21km (13 miles), 2-4 hours biking, Elevation gain: 365m (1200 ft)

Spend a final, tranquil morning at the hotel, or if you prefer one last adventure, join a final ride through the medieval village of San Gusmè to Castelnuovo Berardenga. Here, you can pause at a local bar for a traditional cappuccino or a caffè corretto—a shot of espresso with a splash of grappa. After bidding your leaders arrivederci, you'll travel by private coach to Florence, where your journey concludes.

NOTE: This itinerary is provided as an example only – prevailing conditions and local arrangements may cause variation..