Tuscan Wine Classic: Pienza to Castellina via Siena

Tuscan Wine Classic

Yes, there are hills but your efforts on this tour will be rewarded with sunny Mediterranean ambiance and a spirited flair for hospitality, Tuscany nourishes the soul and leads you to rejoice in the earthly pleasures of daily life.

The route takes you along tranquil country lanes tracing the expanses between farmland crowned with walled villages, ancient monasteries in secluded valleys, and medieval forts. Staying in Pienza, Montalcino, Siena and heart of Chianti, you are sure to experience the true essence of Tuscany, where history and beauty fill the heart as water fills a well.

We suggest, after spinning through rolling vineyards, golden wheat fields and chalky white hills by day, to spend your evenings savoring pecorino cheese, homemade pasta pici, fruity olive oils, and sipping the Tuscan wines Brunello and Nobile.

This tour immerses you in Tuscany!

Upon request longer routes can be provided as well (55-63 miles per day).

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Highlights

• Pienza, a Renaissance town
• Castelmuzio
• Montepulciano, the jewel of southern Tuscany
• Monticchiello, the quintessential Tuscan hill town.
• Bagno Vignoni, a miniature spa
• Monastery of Sant'Antimo
• Wine town Montalcino
• Monte Oliveto Maggiore monastery
• Castello di Brolio

Learn More

Learn more about our self-guided tours or see more bike tours in Italy.

Daily program

Day 1: Pienza
Meet and greet in Pienza, the purest reniassance town in the world, for welcome and bike fitting. Pienza is a remarkable example of reniassance-era town planning. If you have even the least appreciation for beautiful architechture, it's a real treat to stroll around it's cobblestone streets. Take an optional test ride to San Quirico d'Orcia (13 miles/20 km).
Overnight in Pienza

Day 2: Pienza – Montepulciano and vino nobile (34 miles/55 km)
Your tour starts with a circular ride from Pienza. Be sure to stop along the way to visit the remote convent where parts of The English Patient were filmed, and in the enchanting little hamlet of Castelmuzio. By lunchtime you'll come to Montepulciano, the jewel of southern Tuscany. After relaxing a while, return to Pienza with a stop in the village of Monticchiello, the quintessential Tuscan hill town.
Overnight in Pienza

Day 3: Pienza – Montalcino brunello land (29 miles/46 km)
Ride from Pienza to Montalcino, with a pause in fairy-tale Bagno Vignoni, a miniature spa that is among the most unique towns in Europe. You can have lunch in Castiglione d'Orcia, then push on to the monastery of Sant'Antimo, where you might catch one of several vesper services performed each day by the monks. The famed wine town of Montalcino is your destination. Visit the fortress to see a breathtaking view of the entire valley you've just biked.
Overnight in Montalcino

Day 4: Montalcino – Siena and Monte Oliveto Abbey (36 miles/58 km)
Today will take you through typical postcard scenery of Tuscany, Italy’s most photographed region—for good reasons. Following a picturesque crest road, you’ll ride by Monte Oliveto Maggiore Abbey, a Benedictine abbey built in the 13th century and famous for its frescoed cloister and stunning setting. Afterwards, you'll travel through the fascinating area called Le Crete, Tuscany's answer to the Badlands. Here the verdant hills give way to little domes of clay and Tuscany reveals another face of its identity, an unusual, almost lunar landscape of chalk cliffs and gullies soaked in a primeval atmosphere.
Overnight in Siena

Day 5: Siena – Chianti hills (31 miles/50 km)
Ride from Siena to Castellina in Chianti, following the "Chiantigiana" road. Along the way you can visit Castelnuovo Berardenga, a medieval town that marks the gateway to Chianti country. From here you will ride inside the vineyard of famous chianti classico wine passing through many little hamlet. Not far away is Castello di Brolio, a castle and winery that you can visit. There's also the chance to shop at a first-class ceramics workshop. Arrive in time in Radda for a light lunch and enjoy the last 10 km of gentle rolling hills to get to Castellina.

Castellina's medieval street, the Via delle Volte, was originally open to the sky, but over the years houses and shops have encroached on the ancient city walls, covering the street and providing an intriguing underground home for shops and restaurants.
Overnight in Castellina in Chianti

Day 6: Castellina – Greve in Chianti and Panzano (35 miles/56 km)
Circular bike ride to Florence chianti: bike along quiet roads to the three villages that formed the Chianti Alliance centuries ago. Visit Tuscany's forgotten abbeys and hamlets then enjoy a winery tour and taste their supple reds, fresh honeys and rich olive oil. Have a stop at Greve's main piazza, characterized by an original formation of irregular triangular shape, defined by beautiful long porticos. Back via Panzano with preserved the old walls, gate and the keep of the medieval castle. relax by the vanishing edge poolspilling into the countryside of endless vineyards.
Overnight in Castellina

Day 7: Castellina to San Gimignano (optional 36 mile/58 km)
<ore vineyards await us today, but you'll be amazed at how different they look once we get into the district of San Gimignano. Pretty soon you pass Monteriggioni, literally a town-in-a-castle. Barely two hundred yards across, its eighty residents all reside within the picture-perfect round turreted walls that crown the hilltop visible for miles around

Surface and terrain

There are lots of ups and downs on rolling hills and some climbs and challenging hills. The terrain is rarely flat.

Hotels

These are sample hotels and may vary based on availability.

The accommodations are 3- and 4-star hotels.

Relais il Chiostro, Pienza
www.relaisilchiostrodipienza.com

or luxury upgrade:

La Bandita, Pienza
www.la-bandita.com

Hotel Giglio, Montalcino
www.gigliohotel.com

La Villa STR, Siena
www.lavilladistr.it

or luxury upgrade:

Villa del Sole, Siena
www.villadelsolesiena.com

Hotel Palazzo Squarcialupi, Castellina
www.palazzosquarcialupi.com

Luxury hotel upgrade pricing upon request.

Please note any visitor's taxes are not included in the tour price. These taxes range from €1-5 per person daily, payable to each hotel.

Interested in visiting other areas before or after your tour? Visit our hotels page to learn more about lodging options.

How to get there

Tour start
Nearest airport: Rome Fiumicino (FCO) and Florence Peretola, Italy (FLR)
Nearest train station: Chiusi-Chianciano, Italy

From either airport, take a train to Chiusi (www.trenitalia.com/tcom-en). Once in Chiusi you can take a bus or taxi to get in Pienza. Take the bus from Chiusi to Montepulciano. The bus fare is approximately €4 per person, and the bus leaves every 30 minutes (40-50 minute ride). From Montepulciano, take the bus to Pienza (15 minute ride). Please note the bus from Montepulciano to Pienza is not available on Sundays.

Tour end
Nearest airport: Florence, Italy (FLR)
Nearest train station: Castellina, Italy

At tour end, buses and trains are available. By bus, go to Siena station where you can take a direct bus or train to Rome or other destination.

Tips on getting to and from your tour

Dates

Prices

Included services

• 6 nights in excellent 3- and 4-star superior hotels
• 6 breakfasts
• All baggage transfers
• Route maps and itineraries, elevation gain
• Sightseeing, restaurant, and shopping suggestions
• RideWithGPS App: tracks & off-line navigation
• Pick-up of bikes and gear in Castellina
• Water bottle
• Sales tax

Please note any visitor's taxes are not included in the tour price. These taxes range from €1-5 per person daily, payable to each hotel.

Bike rentals

Bikes available for rent (in advance at the time of booking) on this tour are:

• Hybrid touring bike, 27 or 30 speed, equipped with:
  • Aluminum frame
  • Full Carbon
  • Shimano Deore components 
  • Gel saddle
  • Upright handle bar
  • Wheelset: Shimano RS30
• Road bike, 20 speed, equipped with:
  • Full Carbon fiber 
  • Carbon forks
  •  Shimano Ultegra  or 105  – 11/32 –  11 speed
  • Drop handle bar
  • Wheel set: Shimano R561
• Gravel bike
  • Addict Gravel Disc Hmf / Imp Carbon
  • Shifters: Shimano St-R8020 Disc  Dual Control  22 Speed
  • Seat: Syncros Tofino T-Cutout 2.0
  • Wheel set:Syncros Rp2.0 Disc  Syncros Rws
• Electrically assisted bike with 250w Sunstar motor
  • Frame E-Sub 6061 Alloy
  • Bosch Performance 250w System W/ 500wh Power Tube Battery
  • Brakes: Shimano Br-M365 Disc
  • Rear Derailleur: Sram Nx 11 Speed

• Electrically assisted bike with 500w Bosch Internal battery

*More about electrically-assisted bikes >

Equipment included with bike rental:

• Helmet
• Handlebar bag or map holder
• Water bottle
• Repair kit (mini pump, inner tube, tire levers)
• Computer mileage counter
• Lock (one lock with key per 2 bikes)

Bike Protection:
Bike protection can be purchased at the time of booking. You can read more about that HERE.

Pedals:
The bikes will have toe clips or flat pedals. You can also bring your own pedals and shoes, along with the necessary equipment for installing the pedals.

Seats:
If you plan to bring your own seat, please don't bring the seat post. The tour company can assist you with installing.

Helmets:
Helmets are required on this tour. Helmets are included in the tour package; however, we recommend you bring your own helmet for safety and hygiene reasons.

Tour Company