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Tuscan Treasures: From Pienza to Chianti Vineyards
Cyclomundo offers guided and self-guided cycling trips in Tuscany

Self-guided trip: Starts any day from April through October 2016
6 nights/7 days
Daily mileage: From 34 km (21 miles) to 100 km (62 miles, long option). We want to stress that Tuscany terrain is fairly challenging.                                  
Trip starts from Pienza and ends in Radda in Chianti. Pienza is a 1/2 hour drive from the Chiusi train station.
Transfers can be arranged from Florence or Chiusi to Pienza and from Radda in Chianti to Florence.
Accommodations in 3- and 4-star properties
Level: 3/4 (Moderate/Difficult)
From 1,375 euros per person sharing a double room

Tuscan Treasures: Pienza, Siena, San Gimignano & Chianti Vineyards — 6 nights/7 days

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  If you’ve seen Tuscan landscapes on screen or in photographs, you’ve likely stopped to catch your breath and mumble — or perhaps loudly exclaim — “I need to go there!” Once you’re there, you’ll quickly realize that television and magazines (etc.) cannot do Tuscany justice. The flabbergasting beauty of everything will no doubt leave you tongue-tied. (Be sure to unravel your tongue in time to eat and drink wine!)

This cycling tour starts from medieval Pienza and finishes in Castellina-in-Chianti, part of Tuscany’s famed wine country. In between, you’ll pass countless remarkable sites — no fewer than 4 of them (Pienza, Val d’Orcia, Siena, and San Gimignano) have been deemed so exceptional that they’ve earned UNESCO World Heritage Site status. Throughout your journey, you’ll be inspired like many artists who lived and worked in this region.

Rides take place on Tuscany’s iconic rolling terrain, which for some can be easier to look at than to ride on a bike. Cyclists should be in very good physical condition to tackle some of Tuscany’s steep hills.
Day 1: Arrival in Pienza
The closest station to Pienza is Chiusi — 35 km away — on the Rome-Florence train line. The town was conceptualized as a holiday retreat from Rome, and indeed, it’s a bit removed from the hustle and bustle. A taxi or a series of buses can take you there, or we can arrange a car transfer from Florence to Pienza. Check in to your hotel, a former 15th century convent, then set about exploring! Pienza is a masterpiece of Renaissance architectural gems set amidst the quintessential bucolic Tuscan hills.
Day 2: Loop from Pienza through Montepulciano (2 options: 51 km/32 miles, 1,080 meters/3,550 ft. of climbing or 100 km/62 miles, 1,800 meters/5,900 ft. of climbing)
You’ll follow a route that winds through vineyards, cypresses, and medieval villages. If it seems like you’re riding through a movie set, that’s because many popular films were shot here. Ride through hills to the villages of Castelmuzio and Montepulciano, the latter of which makes for a perfect lunch/wine stop. (Montepulciano is home to the famous Vino Nobile di Montepulciano!) Head back to Pienza through Monticchiello… yet another hilltop village!

Day 3: Pienza — Montalcino (2 options: 44 km/27 miles, 910 meters/2,980 ft. of climbing or 72 km/45 miles, 1,455 meters/4,765 ft. of climbing)
Today’s ride will take you to Bagno Vignoni, a thermal spa town that dates back to Roman times, before reaching the beautiful Castiglione d'Orcia in the UNESCO-protected valley. The monastery of Sant'Antimo is your next stop — with luck, you will hear the melodious sound of monks chanting. Montalcino, another notable wine town, is your destination. Definitely go for a tasting or three at a local cellar and seek out the famous local Brunello. The town’s fortress offers unbeatable views over the Val d’Orcia.
Day 4: Montalcino — Siena (3 options: 52 km/32 miles, 870 meters/2,860 ft. of climbing or 59 km/37 miles, 950 meters/3,120 ft. of climbing or 97 km/60 miles, 1,845 meters/6,050 ft. of climbing)
Have your camera ready to capture some typical postcard scenery today. Following a picturesque crest road, you’ll ride by the Monte Oliveto Maggiore monastery, home to a number of frescoes. The monastery makes for a nice lunch spot before cycling on to Siena, one of Tuscany’s most lively cities. Make the best of your afternoon and explore its countless treasures, such as its unfinished Duomo and the famous Piazza del Campo. Twice a year, the Palio horse race pits riders from the ten of the city’s 17 contrade (districts or wards) against each other as they circle the piazza.
Day 5: Siena — San Gimignano (71 km/44 miles, 1,315 meters/4,310 ft. of climbing)
The vineyards and scenery remain as lush as ever today, but we have some new (well, old) sites on your list. First is Fungaia, a hamlet on the medieval Via Francigena pilgrim trail. Next you’ll encounter the Etruscan Casole d’Elsa, a fortress that predates ancient Rome! On your way to San Gimignano, you’ll ride through San Donato and take its distinctive skyline of stone towers from a distance. San Gimignano is exceptional, and we cannot recommend enough an early arrival to discover this fascinating place. Bring your appetite, too, for the town is home to number of exceptional restaurants in historic buildings.
Day 6: San Gimignano — Castellina in Chianti (2 options: 40 km/25 miles, 910 meters/2,980 ft. of climbing or
61 km/38miles, 1,280 meters/4,200 ft. of climbing)

Another day of hill climbing awaits you, but luckily the many recovery sites include medieval Barberino and Tavernelle, gateway towns to the Chianti Classico wine-producing region. The scenery is as rich and full-bodied as the wine made here! Continue along a winding panoramic road to Castellina in Chianti. The commune’s high position makes it feel like a balcony, from which you can overlook the esteemed vines.
Day 7: Departure (or optional loop via Monteriggioni: 34 km/21 miles, 590 meters/1,940 ft. of climbing)
After breakfast, depart Castellina in Chianti at the time of your choice. There are regular buses to the train station in Siena, or direct buses to Florence. Note that you may opt to ride a short loop that will take you to Monteriggioni, a beautiful town worth a visit before your cycling tour officially ends.
Booking & Pricing
From 1,375 euros per person based on double occupancy.

  • 1,375 euros in April and October. Single supplement is 400 euros
  • 1,395 euros in May, June and September. Single supplement is 410 euros
  • 1,415 euros in July and August. Single supplement is 425 euros

These prices include:

  • 6 nights' accommodation in 3- and 4-star properties of character
  • Daily breakfast
  • Meeting with our local representative
  • Luggage transfers
  • Marked maps and/or cue sheets and route notes
  • Tourist information
  • Assistance if necessary (you will be provided with our local rep’s mobile number)
  • Service charges and most taxes

These prices do not include:

  • Nominal city taxes, to be paid in cash directly at each hotel
  • Expenses of personal nature
  • Travel insurance
  • Bicycle rentals. Carbon racing bikes rent for 210 euros. Hybrid bikes are available on request at the rate of
    110 euros. These prices include the 20-euro drop-off fee for the bike’s return to Pienza.
Please book online at your earliest convenience as this trip is subject to hotel availability. Our e-mail address:
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