Tuscany is an iconic name, symbolizing the good life - a vacation to enjoy all that is good: food, sun, lifestyle, wine, amusement, and relaxation. The culture of the region adds charm, and you can indulge yourself in this opulent way because you will cycle the famous undulating countryside. This Tuscany cycling tour starts in Montepulciano and goes to Pienza, where along the way you will visit the villages that have made Tuscany famous. You can enjoy very charming 3/4 star accommodations and devour your choice of divine mediterranean cuisine. The hilly terrain makes this tour somewhat challenging!
Duration: 7 days / 6 nights; note that a 4 night option is also available as well.
Dates: March 15-November 15. This is self-guided touring and offers total freedom of dates - you can choose whatever dates you wish. We can accomodate small parties of 2 persons up to large groups. Custom guided groups are possible for groups of 6 or more; please inquire.
Level 3 - Consistently hilly countryside with mostly hilltop finishes; challenging terrain can be moderated or made more challenging by daily mileage.
Ride options - longer/shorter
Custom tours for groups
Marco and Giuliana are our on site experts, they live in Tuscany and will meet you for orientation on arrival day as well as provide emergency support throughout your trip.
"I wanted to write and let you know how marvelous out trip to Tuscany was and thank you for arranging such a wonderful biking tour. Giuliana and Marco were terrific and made sure we had everything we needed. The route maps were easy to follow, our hotels were terrific and the bikes satisfactory for our Tuscany adventure!! "
- Julie S./USA
Click on a day to see that days itinerary.DAY 1 DAY 2 DAY 3 DAY 4 DAY 5 DAY 6 DAY 7
Day 1 | Arrival Day - we will meet you at Montepulciano & vino nobile. Arrive by train at Chiusi and either bus or taxi to hotel.
This splendid little town - whose artistic and architectural heritage led it to be called the Pearl of the Cinquecento - has preserved its beauty intact. Going up the steep streets of its outlying districts you will discover beautiful palazzos and churches imbued with the unparalleled art of foremost Renaissance architects. Orientation meeting at 6pm and then dinner on your own. Some foods to try in Italy
The oldest hotel in town, the Albergo Il Marzocco was built in 1500 as a farm of the nearby convent....
Day 2 | Cortona & Tuscan sun; Bike from Montepulciano to Cortona spinning across val di chiana. Distance 45 km.
From Montepulciano start a pleasant five-mile descent through the vineyards, where the only sound is the wind in your hair. After a very brief climb, you pass through the town of Valiano and plunge into some of the most beautiful vineyards in Tuscany. Relaxed and glowing, it's time to set off on a long, slow climb towards Cortona, the delightful hilltown made famous by Frances Mayes in her bestselling novel Under the Tuscan Sun. Lodging hotel San Michele or hotel San Luca. Breakfast included. (B)
Cortona (AR) Italy
The Hotel San Luca is located in the Piazza Garibaldi in the historic centre of Cortona (within city...
Day 3 | Montisi & le Crete area - Bike from Cortona to Montisi via Trequanda. Distance 50 km.
Enjoy the 3 miles downhill and cycle in the valley for a while. You will visit the mediaeval village of Trequanda, one of the most unspoilt areas of the province of Siena, and was developed around a 13th century castle of which a cylindrical tower with battlements still remains today. Your goal is the ancient borgo of San Giovanni d Asso, natural bridge between the "Crete Senesi" and the Val d Orcia, famous worldwide for its valuable white truffle, is rich with farms, hamlets and castles, which are reminiscent of the colors of the paintings of the Renaissance. Lodging Locanda di Montisi. (B)
The Locanda di Montisi is a charming accommodation in Montisi, near San Giovanni d'Asso. The Locanda...
Day 4 | Siena & Piazza del campo - ride from Montisi to Siena via Monte oliveto maggiore abbey. Distance 45 km.
Today you will spin to the 14th c. Abbey of Monte Oliveto Maggiore, and view the famous Renaissance frescoes at the monastery. In the afternoon you will arrive in Siena, a medieval city with beautifully preserved Gothic architecture. The entire city of Siena was built around the Piazza del Campo. Here you will have time to shop while exploring the many hidden medieval walkways. Lodging: hotel chiostro del carmine or hotel duomo. (B)
Siena, Toscana, Italia
Il Chiostro del Carmine is a restored 14th-century monastery, with great views of the countryside. I...
Day 5 | Montalcino & Brunello - ride from Siena to Montalcino via Murlo and castello di grotti. Distance 52 km
Today in Tuscany we bike to the blessed land of the famed Brunello wines. The biking is challenging but one of the most beautiful rides in Tuscany: pass through Murlo, a castle-village on a hill slightly more than 300 metres high that dominates the valley of the Crevole,. In the late afternoon, enjoy free time to roam the narrow streets Montalcino, a picturesque town famous for Brunello wines and medieval architecture. L odging hotel Il Giglio or dei Capitani. (B)
A charming retreat in the heart of Montalcino, a family-run Hotel in a warm and quiet building, faci...
Day 6 | Pienza and sheep milk cheese; Bike from Montalcino to Pienza via sant’antimo and Bagno vignoni spa. Distance 46 km.
Reach monastery Sant Antimo with 9 km gentle downhill, where you might catch one of several vesper services performed each day by the monks. Soon we start uphill and reach Castiglione d Orcia and follow a long downhill stretch to the enchanting spa town of Bagno Vignoni, a minuscule village whose ancient stone buildings cluster around a pool of warm thermal waters. Then push on to the town of Pienza, then head west past ancient vineyards, stone farmhouses and bright green pastures. Lodging hotel il chiostro, Corsignano, or piccolo hotel la valle. (B)
Corso Rossellino, 26
Relais Chiostro di Pienza is situated in the heart of Pienza, a Renaissance city planned by Rosselli...
Day 7 | Departure Day - taxi to Chiusi for fast train connections
Departure after breakfast, at your leisure. If you want to go on to Florence, we can arrange transportation and hotels. Trains, car rentals can be arranged as well additional stays throughout Italy. An added day in Siena is recommended to allow for more visitation; or to extend the cycling, from Pienza we can arrange a 66km ride to Radicofani. (B)
Deluxe lodging 3 and 4 stars - double room with private bath, buffet breakfast daily, all luggage transfers from hotel to hotel, local emergency support throughout your tour during daylight riding hours, arrival orientation and bike set up, route maps, route cue sheets with suggestions for visitation and site information, all pre and post travel planning services and a package of pre-travel documents sent electronically to help you prepare for your trip. Bike rental is not included in the price but is available on all tours and is highly recommended.
There is an upgrade option available for this tour as well with upgraded hotels or upgraded rooms; please see the price section. All hotels in either the 3 and 4 star version or upgraded 4 star are superior hotels with excellent locations and amenities. See the information shown for each day in the Itinerary tab.
Lodging on this tour is the same as that found in guided group tours costing $4000 and more!
Cycling in Tuscany is one of the best ways to experience this famously romantic countryside. Traveling from one famous village to another along small country roads, this bicycle tour can be adapted to your needs.
Accommodation: See the list of hotels in the Itinerary tab for the most up to date hotel information.
On the 3 and 4 star tour we include: : Montepulciano - Albergo il Marzocco, Cortona - San Luca, Montisi - Locanda di Montisi, Siena-Chiostro del Carmine; Montalcino-Hotel Il Giglio or dei Capitani, Pienza - Piccolo hotel La valle, Corsigno, or Il Chiostro. These properties are all excellent hotels offering views, and charming typical Tuscan ambiance. They are also in demand, so last minute requests can be difficult. In case of no availability; we will check equivalent alternative hotels that may require a change in price.
Basic Rooms: a less expensive option using the most basic rooms in the above hotels available too; see the Rates tab for the numbers.
Upgrade hotels: Montepulciano: Locanda San Francesco; Cortona - Villa Marsili; Siena - Palazzo Ravizza; Montalcino - Vecchia Oliviera; Pienza - Relais Il Chiostro, sup. room.
Ride options - longer/shorter
Custom tours for groups
Hybrid Bike Rentals are available for a supplement of 105 euros, please see the Bike Rental tab for all details about the bikes we offer. Road bikes are also available for 150 euros.Private transfer Chiusi to Montepulciano or Pienza: 67 euros up to 4 persons.
Bike rentals are available for every tour. We offer top quality custom built hybrid and road bikes.
Note: pedals are flat or with clips; if you bring your own clipless pedals and shoes we can install them.
Bike: [Click for image and more details ] Custom hybrid; aluminum frame with carbon fork, Bikes come equipped with handlebar bag, lock, water bottle, gel saddle, tire repair kit, cycle computer. Hybrids are fitted with thin tires for better road performance. Rental rate is 105 euros for the tour.
Racing models also available see details . Rental rate is 140 euros for the tour.
Hilly terrain, rated as intermediate to advanced. All towns where lodging is located are perched hilltop villages.
A Cannondale tandem is also available for experienced tandem riders. Persons from 5 ft to 6-5 can be accommodated. Bike quality is top; averaging $1500 each retail.