Cycling Val d’Orcia - Around Pienza Join us on this total immersion into Tuscany. Our back roads head into rolling hills and through the fortified medieval villages of an untouched Toscana. The goal of this bike trip is to also enjoy the genuine cucina toscana: fruity olive oil, pecorino sheep-milk cheese and classic best Tuscany wine: Brunello -that has made Tuscany so famous- Chianti and Nobile. You will taste a selection of our favorite producers during our special events. Travelling with a small group of fellow adventurers and Tuscany's leading biking guide, you'll enjoy a wonderful combination of nature, culture, cuisine and fun. Highlights ● Full immersion in Val d’Orcia, Unesco site since 2004 ● Stay in Pienza the ideal renaissance city ● Riding through scenic landscapes where “English Patient” & “Gladiator” were filmed ● A private tour of the cantina of Brunello in Montalcino, the biodynamic Corte Pavone

Itinerary Difficulty Rating: 3/4 Moderate to Vigorous - Good physical fitness required; 28-40 miles cycling per day with elevation gains and loss close to 3000’ per day. Tuscany is hilly with few flat sections. Previous road cycling experience required. Support vehicle is provided.

Itinerary October 11th Day One – Welcome To Pienza! Benvenuti in Toscana Meeting point options: Chiusi train station at 11.00am. Transfer to Pienza by van, 40 minutes from Chiusi Train Station. Montecatini Terme at 9:00am, transfer to Pienza (~2 hours) Pienza is well known as the perfect town , a remarkable example of Renaissance-era town planning. If you have even the least appreciation for beautiful architecture, it is a treat to stroll around its cobblestone streets. Pienza is also a veritable gastronomic paradise, famous for Pecorino sheep milk cheese production. After a bike fitting, we head out on our first ride, a loop to Radicofani, a medieval and enchanting village with a Rocca (castle tower) dating from 1200. After a stroll around the stately old town, we head back into the country, along some of those winding cypress-lined roads back to Pienza. Our charming Hotel is housed in a 15th-century convent in a quiet, secluded location right in the center of Pienza. Entirely rebuilt between 1459 and 1462, itself is a rare masterpiece: it was the brainstorm of Pope Pius II. Welcome dinner at La Bandita Townhouse. Lodging at hotel Relais Il Chiostro in Pienza Included meals: light lunch & dinner Itinerary difficulty: 3/4 - Moderate to Vigorous Distance 64 km/40 miles Elevation gain 2,867’ / Elevation Loss 2,868’ October 12th Day Two – Montepulciano & Vino Nobile Loop ride to Montepulciano and Monticchiello. We start our day with a pleasant downhill, following a route that winds through a scenic landscape checkered with vineyards, cypresses, and medieval villages. Among the sites we ride through include the hilltop villages of Castelmuzio and Petroio. We arrive to Montepulciano, known as the Pearl of the Sixteenth Century, and for the production of Vino Nobile. We visit Salcheto, one of the emergent wineries and our favorite! After a wine tour and a light lunch with fresch pici pasta at the cellar, we cycle back to Pienza through Monticchiello… another hilltop village! Enjoy old cypress trees that line the route in the Orcia valley that inspired Renaissance painters. Dinner at La porta. Lodging at hotel Relais Il Chiostro in Pienza Included meals: breakfast, light lunch & dinner Itinerary difficulty: 3 - Moderate Distance: 52 km/ 32 miles Elevation gain 2,910’ / elevation Loss 2,972’ October 13th Day Three – Montalcino brunello land Today’s ride will take you to Bagno Vignoni, a thermal spa town that dates back to Roman times right before reaching the beautiful Castiglione d'Orcia. Enjoy a long downhill to the monastery of Sant'Antimo where you might catch one of several vesper services performed each day by the monks. On your way to the Etruscan village and wine town of Montalcino, where you will stay , you’ll pedal through magnificent vineyards. Montalcino is a fortified town which was used as a shelter by Siena nobles during the 16th Century, but today it is even more famous thanks to the production of one of Italian’s premier fine red wines, Brunello di Montalcino, visit the fortress to see a breathtaking view of the entire valley you've just biked. Late afternoon Wine tour at our favourite biodynamic and organic winery Corte Pavone. Ride back via San Quirico or by van. Lodging at hotel Relais Il Chiostro in Pienza Included meals: breakfast, light lunch & dinner Itinerary difficulty: 3/4 - Moderate to Vigorous Distance: 46 km/28, 5 miles Elevation gain 2,900’/ Elevation loss 2,703’

October 14h Day Four –Siena, Etruscan and Palio race Ride towards Siena crossing the stark and alluring "lunar" terrain of the Crete Senesi region. First stop is San Giovanni d’Asso, the truffle town in Tuscany. Once arrived outside Siena walls you'll have time to take a leisurely stroll around this medieval art city in the afternoon and to visit Piazza del Campo, Torre del Mangia and the famous Duomo. The main square is famous because here it is held twice a year the disputed “Palio” horse race, which opposes the 17 contrade of this fascinating city. Transfer to Montecatini by late afternoon – hotel on your own. Included meals: breakfast, light lunch Itinerary difficulty: 3 - Moderate distance 50 km /32 miles Elevation gain 1,938’ / elevation Loss 2,957’

Group Size: 4 - 12

Price & inclusions

Tour start Chiusi train station, approx. 11 am October 11, Thursday From Rome: 1 hour 40 min direct train ride From Florence: 1 hour 30 min direct train ride

Tour Start Montecatini Optional Extra night before trip in Montecatini (October 10th) and shuttle to Chiusi to meet group on the 11th at 9:00 am.

Shared double, per person 900 euro 165 euro extra Single room (pending availability as small hotel might not have enough)

1150 euro 190 euro extra

Inclusions: Three nights in excellent four star hotel; three breakfasts; four lunches, three dinners; guidance, van support, transfer to Montecatini Terme on Day 4; Route notes, maps, elevation gain and city map; All Baggage transfers; high quality road, hybrid bikes, e-bike & equipment. Not included : Airfare to Italy, alcoholic/non-alcoholic beverages, gratuities, travel insurance, laundry expenses and items of a personal nature

Weather October is considered to be one of the best months to visit Tuscany. The average temperatures in October are set between 11 and 21°C . However, the complex topography of Tuscany includes micro-climate differences within its different regions. Layering is therefore important, as well as be prepared with a proper rain and windproof jacket. Packing List: Layering is key to remaining comfortable while on an active trip. To achieve maximum comfort with minimum weight, you need versatile layers that mix and match to create the right amount of ventilation, insulation, and weather protection.

Luggage: ● Medium duffle or rolling soft-sided luggage ● Luggage lock ● Packing cubes/stuff sacks

Clothing: ● Casual clothing/shoes for travel and city wear

(lightweight, easily washable) ● Light rain/windproof jacket ● Mid-weight fleece/softshell ● Underwear/sports bra (quick drying) ● Sleepwear

Cycling: ● Cycling helmet – mandatory (You can borrow

one of ours with advance notice) ● Stiff-soled cycling shoes

○ Bring your own clipless pedals and mountain bike shoes with recessed cleats (optional)

● Cycling Jerseys ● Padded cycling shorts (x 2) ● Arm and leg warmers ● Regular biking gloves ● Eyewear - Biking glasses ● Lightweight wind jacket ● Rain jacket/pants/shoe covers (just in case!)

Assorted Personal Items: ● Water bottle (cycling) ● Sunblock and lip balm with SPF ● Sun hat ● Sunglasses ● Personal toiletries (toothpaste, toothbrush,

hand sanitizer, etc.) ● Personal first aid kit, medications ● Camera/memory cards/battery ● Electronics charger ● Earplugs and eye shade