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Self-Guided Bicycle Tours in Italy: Bicycling Cortona, Montepulciano and Montalcino in Southern Tuscany

This self-guided tour of Tuscany covers a small but stunning part of Tuscany near the border with Umbria. Discover the beauty of Montepulciano, Cortona, Pienza, the Val d'Orcia, Montalcino and its famous Brunello wine, and Siena. This is a relaxed tour with two three-night stays so you are not always packing. If you wish to take a day off, two of your hotels have pools (available in season). The tour ends in Siena where you may wish to spend an extra day or two. Of course, food and wine also play an important role on this tour; you'll taste homemade pasta, local cheese, and typical soups of Tuscany, so Buon Appetito!

For more information download the Tour Factsheet

Request space on this Self-Guided Bicycle Tour

Day 1: Arrive at Chiusi/Chianciano Train Station, transfer to hilltop hotel

Highlights: Fit bikes and take a warm-up ride amid the vineyards of Southern Tuscany

Arrive at the Chiusi Chianciano train station today early afternoon and we'll shuttle you to Borgo Tre Rose, your home for the next three nights. If your arrival time differs, please contact us and we will try to accommodate your travel schedule. We'll fit your bikes and suggest a short loop ride. Dinner is at the hotel restaurant for the next 3 nights. Daily Mileage: 22 - 30 km (14 - 19 miles)

Day 2: Loop Ride to Cortona

Highlights: Cortona, Etruscan Museum, gelato

We suggest a ride today to the Etruscan town of Cortona. You'll pass along the Val di Chiana, famous for the chianina steak bistecca di chianina before reaching the imposing town of Cortona on the top of the hill with its defensive Etruscan, Roman and Medieval walls surrounding the historic town. Cortona is an ideal stop for lunch and for some sightseeing. A must-see is the recently restored Etruscan Museum or the Museo Diocesano with Fra Angelico paintings. Our favorite gelateria is in the square in front of the museum. Daily Mileage: 44 km (28 miles)

Day 3: Loop Ride to Montepulciano

Highlights: Medieval City Center, Vino Nobile di Montepulciano

Montepulciano is famous for the production of Vino Nobile di Montepulciano, and your ride today takes you there. After a stroll along the medieval streets of this village, you can stop to visit one of the typical wine cellars in town. Take time for lunch before returning to the hotel where the restaurant has prepared you dinner. Daily Mileage to Montepulciano: 32 - 47 km (20 - 29 miles)

Alternatively, you may choose to ride along the shores of Lake Trasimeno today. The lake is famous for Hannibal's defeat of the Roman army after crossing the Alps with elephants! Along the ride you'll pass close to the tiny Lago di Chiusi before reaching the fortified village of Castiglione sul lago. If you have the time you might want to take a boat ride on Lake Trasimeno to Isola Maggiore. After a stroll on the passeggiata and lunch on your own, continue back to Borgo Tre Rose. Daily Mileage to Lake Trasimeno: 35 - 59 km (22 - 37 miles)

Day 4: Bicycle to Pienza and San Quirico d'Orcia

Highlights: Pienza and the UNESCO World Heritage Landscape of Val d'Orcia

Pack your bags and head to San Quirico D'Orcia today, your home for the next 3 nights. Luggage will be transferred directly to the hotel while your ride takes you to one of the first planned Renaissance towns, Pienza. With the help of a number of prominent architects Pope Pius II turned his small hometown into a piece of art in the 16th century. The Orcia River valley will be the focus for your rides over the next two days. Daily Mileage: 39 - 48 km (24 - 30 miles)

Day 5: Loop ride to Montalcino and the Abbey of Sant'Antimo

Highlights: Montalcino, Abbey of Sant'Antimo, Bagno Vignoni

Pedal through vineyards and wheat fields this morning as you make your way to the Etruscan village and wine town of Montalcino. This fortified town was used as a shelter by Sienese nobles during the 16th Century, but today is even more famous for producing one of Italy's premier red wines, Brunello di Montalcino. Our scenic route takes you to the famous Abbey of Sant'Antimo and then on to Bagno Vignoni, a Medieval spa town. Daily Mileage: 54 km (34 miles).

Day 6: Loop ride to the Abbey of Monte Oliveto Maggiore

Highlights: Trequanda, Abbey of Monte Oliveto Maggiore

Our loop route today takes you to Trequanda first and then to the Abbey of Monte Oliveto Maggiore, a Benedictine abbey built in the 13th century and famous for its frescoed cloister and stunning setting. You are back in San Quirico this afternoon in time for a swim or to enjoy the spa center of the hotel. Daily Mileage: 66 km (41 miles).

Day 7: Bicycle to Siena

Highlights: Siena, beautiful southern Tuscan Landscape

The full beauty of the Tuscan landscape, from the lush green fields of the Orcia Valley to the barren, chalk hills of Central Tuscany, unfolds before you today as you leave San Quirico and pedal to Siena. Often described as Italy's best preserved medieval city, Siena rivaled Florence for dominance in Tuscany during the 1300s. You'll have time to take a leisurely stroll through this medieval art city this afternoon to visit Piazza del Campo, Torre del Mangia and the famous Duomo. There are a plethora of charming restaurants to choose from in the city center. Daily mileage: 59 km (37 miles).

Day 8: Tour ends in Siena

Highlights: Enjoy Siena for another day or two

Your tour ends after breakfast this morning, but Siena is certainly worth another day or two. Trains are frequent and fast to Florence or south to Rome.
  • Highlights
    Montepulciano, Montalcino, Siena and its beautiful town center, Rolling hills of Tuscany
  • Includes
    7 nights in 3 or 4 star hotels; 7 breakfasts; 3 dinners; use of a high quality racing or hybrid bicycle; bike delivery and collection; use of GPS with preloaded tracks; roadbook and map; suggestions for dinners; luggage transfers
  • Countries
  • Begin/End
  • Arrive/Depart
    Rome Fiumicino (FCO), Florence Airport (FLR) or Bologna Guglielmo Marconi Airport (BLQ)
  • Total Distance
    366 - 500 km (227 - 311 miles); 3 night stays allow for rest days for those who wish
  • Daily Distance
    0 - 80 km (0 - 50 miles); additional mileage is always available
  • What to Expect
    Hill and ridge rides in one of the world's most stunning landscapes. Easy loop rides for those who prefer to spend time by the pool (depending on the season)
  • Rating
    The beauty of multiple-night stays is you can take long or short rides at your pleasure. Each day involves some hills but you decide how far and how many.
  • Notes
    You can make this a 5 to 15 days tour. Ask for details. Tour Factsheet
  • Terms
Dates Price Single
Tour departs every day.
Hotel upgrade possible (ask for details).
City taxes not included.

GROUP DISCOUNTS 5% (on groups of 4 or more)
Electric bikes available for an extra charge
€1445 400 € (singles traveling with others pay a 350 € supplement) Request space on this tour now!

Click on the "pins" for details about each day's highlights.

Map Key

Green pinStart
Yellow pinCity (on route)
Red pinEnd
Other city dotCity (not part of route, provided for reference)
I wanted to thank you for everything that you did to help set up my trip. It was absolutely wonderful! The scenery was breathtaking, the riding was challenging (especially with the high temperatures), but doable, and the accommodations were fantastic! The bike was outstanding as well- a perfect choice for the type of terrain. The bike bag with the mini-panniers was perfect....yes, I did pick up a couple of bottles of wine along the way!! The written directions and mileage notations were very easy to understand- I think I only missed one turn, but after a few hundred meters I quickly reversed course and was back on track. The suggestions for restaurants were good ones- the Caffe'' Poliziano in Monetpulciano was certainly a highlight! The roads chosen were excellent. I had to smile to myself when I got to the last few kilometers outside of Siena and you sent me up that steep gravel road...kind of a "parting shot", I thought! The personnel at each of the three hotels were extremely helpful and pleasant- they could not have been nicer. In fact, the only thing missing was sharing a celebratory bottle of wine with you at the finish line in Siena!
Tim G.
July 2015
I was riding a perfect bicycle through a perfect countryside. I want to buy my bike from you! I loved being self guided! About the route notes provided: A wealth of information! We had the opportunity to help some other confused bike riders from a different company with THEIR route notes and that helped drive home how truly excellent your packets are. That you provided alternate routes was wonderful. The trip options for long and short rides were fantastic. This was a magical trip for me. The scenery and the biking were sublime.
John C.
June 2014
Our favorite experience on this trip was basically pulling into the major center after a long ride and then having time to wander and have lunch and wine :-)
Chuck D.
April 2014
It is hard to believe, but there were NO flats, NO slipped chains, NO accidents. The sights were memorable. Your step-by-step directions were also most helpful and took us seamlessly from A to B. Your company runs a smooth ship and we appreciate the personal attention that you have given to us in your planning. We will recommend you to our friends and are already talking about doing a trip with your company soon!
Mahadevan K.
September 2013
Between the scenary, weather, food, accomodations and route it was the best bike tour I have experienced.
Frank S.
May 2013
Travelling through and being so close to the wonderful countryside - we hadn''t had a cycling holiday before.
Alan D.
August 2012
Thank you for the wonderful personalised service before and during the tour. I had extra nights in hotels with all the arrangements made for me. Much appreciated.
Patrick L.
May 2012
Our favorite experience on this trip? Food, wine and riding. We had an excellent time on our tour.
Mike W.
August 2011
I just want to thank bike rental plus for a tremendous cycling experience. The scenery was fantastic and the food and wine even better. The hotels greatly exceeded my expectations, especially the Borgo Tre Rose. The road book was just tremendous- the descriptions and maps of the towns were very interesting and the route descriptions were very clear- I never got lost even once. I rarely visit the same place twice but I will come back to Tuscany again because the whole experience was so perfect. Thanks again and see you next year.
Frank S.
May 2013
I would recommend this self guided tour to a friend? Yes, we''''''''''''''''''''''''''''''''''''''''''''''''''''''''''''''''re raving about your company!!!!
Judy I,
Colorado, USA
June 2012
We have enjoyed the entire trip, so it is very hard to choose our favorite experience. I think that cycling on the tandem with my wife through the Italian countryside, with beautiful scenery, passing through small and old towns, enjoying delicious local food and wines was our favorite experience.
Wolfgang Harry L. F.