Moderate, Challenging
Difficulty level
Activity (Bike)

Italy: Tuscany Bike Tour

Eight nights; eight days of bicycle touring among the hill towns and quiet side roads of Southern Tuscany.

“Scenery was fantastic, everywhere I looked it was another postcard shot!” – Kay P.


  • Rewarding cycling with Renaissance backdrop of cypress trees, olive groves, vineyards, and verdant hills.
  • Historic UNESCO town of Pienza.
  • Two nights amidst the wine region of Montepulciano.
  • Cycling through the UNESCO recognised landscape of Val d’Orcia.
  • Etruscan necropolis at Sovana.
  • Exquisite cuisine and ample options for wine, honey, and olive oil tastings.
  • Tyrrhenian Sea views and opportunities for ocean swimming.



Learn about our difficulty-rating system

Tuscany is a hilly region with most towns strategically situated on hill tops, so be prepared for some climbing. But we’ve designed this Italy: Tuscany Bike Tour to minimize climbs and maximize descents, and we’ve kept daily distances moderate or short to allow for a more leisurely pace and extra time to enjoy the amenities, making it an ideal choice for most recreational cyclists. Extra mileage is possible for riders wanting more challenge. Electric bikes are available to make the route suitable to almost any ability. Riding surfaces are almost entirely paved and traffic-shared with occasional gravel sections that are typically well suited to hybrid bikes.

Daily Distance:

  • DAY 1: ~35km
  • DAY 2: ~23km, 34km or 62km
  • DAY 3: ~25 km
  • DAY 4: ~42 km
  • DAY 5: ~53 km
  • DAY 6: ~48 km
  • DAY 7: ~36 km
  • DAY 8: ~38 km
  • DAY 9: Transfers & Farewells

Start: Camucia-Cortana train station, 11:00, day one. Visit TrenItalia for train schedule and fare details.

Finish:  09:00, day nine, at either Talamone or Orbettello Monte Agentario train station.

Please contact us to arrange alternate plans, if necessary.


Camucia-Cortana to Montepulciano 35km

Meet at the Camucia-Cortona train station mid-morning where you will be fitted to your rental bikes and briefed on route materials. Spend the afternoon cycling a leisurely route toward Montepulciano, arriving at your countryside villa late in the day. LD (Meal inclusions provided for guided trips. Self-guided trips include breakfast only)

Villa Cicolina, Montepulciano


Montepulciano Loop 23km, 34km or 62km

Choose from three loops of varying distances through the hilly countryside surrounding Montepulciano. These routes avoid the biggest climbs and busiest roads in the region and allow time for relaxing by the pool and late afternoon exploration of Montepulciano, one of the most charming hilltop towns in Tuscany. Fabled to be the seat of Etruscan kings, Montepulciano was established as an important religious center and enjoyed political allegiances with Florence, bringing the wealth and splendor of some of the most important architects of the renaissance. Enjoy a quiet stroll among stone houses the many car-free streets, gaze across the surrounding farmland from one of the town’s many look-offs, or simply enjoy people-watching from one of the cafes surrounding the Piazza Grande. BL

Same lodging


Montepulciano to Pienza ~25km

You will have the chance for a final visit to Montepulciano this morning before a gradual 5km climb to the highest elevation point for the day. From here, your descent brings you a through beautiful countryside of the Val d’Orcia to Monticchiello, a small medieval town ideally located for a mid-ride break. Descend to the valley floor, and pace yourself for the climb into the UNESCO heritage site of Pienza, a lively town known for its fragrant pecorino cheese. BLD

Relais Il Chiostro Di Pienza or Hotel San Gregorio, Pienza


Pienza to Castel del Piano ~42km

Your ride today starts in the heart of the UNESCO World Cultural Landscape of Val d’Orcia. Cycling along cypress-lined roads through cultivated fields of wheat and olive groves with the lava dome of Monte Amiata in the distance, you will feel as if you are in the midst of a renaissance landscape painting. Today’s climb begins just outside the foothill town of Campiglia d’Orcia and ends near Vivo d’Orcia where you will stop for lunch and enjoy long vistas over the valley. The remainder of the day will be spent descending through shady tree-lined roads along the north slope of Monte Amiata, before reaching your accommodation in the comune of Castel del Piano. After checking into your accommodation, take time to explore the warren-like narrow streets and passageways of the historic town center on foot before an independent dinner. BL

Grand Hotel Impero, Castel del Piano


Castel del Piano to Sorano ~53km

A gradual morning climb heading south along the eastern foothills of Monte Amiata will give way to a long, pleasant descent through the Fiora river valley. In the small medieval town of Sovana you will have the chance to explore an Etruscan necropolis where high relief statues and burial chambers are carved from the limestone Tufa. The nearby Vie Cave is a natural passageway which was once used to reach burial grounds and later developed into more major transportation corridor. The artisan shops and cafes peppering the brick-paved main streets of Sovana are worth taking time to explore. Your ride ends with a short climb into the medieval hill town of Sorano, built upon an outcrop of volcanic tuff. BLD

Hotel della Fortezza, Sorano


Sorano to Scansano ~48km

Following breakfast, your ride today descends into the historic frontier town of Pitigliano. Once home to a large and flourishing Jewish community, the historic old town is still known as “Little Jerusalem”. Although the Jewish population is quite diminished, the restored synagogue remains and continues to host periodic services and is the site of a small community museum. After spending some time exploring the narrow streets, enjoy an invigorating ride through the vineyards and farms of the Fiora and Albegna river valleys. After 10km you will pass near the fortified hill town of Montemerano, a charming hamlet commissioned by the Aldobrandeschi family in the 13th century. Though a bit of a climb, the magnificent views and quiet charm make this a good lunch stop option. The remaining route will climb through vineyards of Sangiovese grapes, known locally as Morellino, the basis for the town’s most famous export, Morellino di Scansano. BD

Antico Casale di Scansano, Scansano


Scansano to Capalbio ~36km

Enjoy a day of quiet cycling through rolling farm country as you gradually descend out of the mountains toward the Tyrrhenian coast. Forested hills and vineyards gradually give way to olive groves and fields of wheat, with views of the ocean and Monte Argentario in the distance. Your ride today ends in the picturesque hilltop village of Capalbio. BLD

Hotel Valle del Buttero, Capalbio


Capalbio to Porto Santo Stefano ~38km

On your final day of riding, you will join the coast at the resort town of Ansedonia, famed for the ruins of the nearby Roman town of Cosa – a site of archaeological significance due to the extent of its excavation. The harbor of Cosa remains the earliest known Roman port in existence, with extensive masonry piers and elaborate channels cut through the limestone cliffs which are thought to have kept the main channel free of sediment. After an independent lunch in Ansedonia, a 7km ride along a sandy neck through coastal pine forests in the Feniglia natural reserve connects you with the headland created by Monte Argentario. The remaining coastal ride follows quiet roads and dedicated cycle track along an old rail bed through tunnels carved in the sea cliffs into the port town of Santo Stefano. Your day will either end in Santo Stefano or after a short van transfer up the shore to the coastal village of Talamone. BD

Albergo Belvedere, Porto Santo Stefano, or Hotel Capo d’Uomo, Talamone


Transfer to train station and farewell

After breakfast you will transfer to the train station where connections are available to Pisa, Rome, or other European destinations. Buon viaggio!

All details and pricing are subject to change without notice.


2024 Guided:

  • May 19-27
  • Sep 22-Oct 1

Self-Guided available any dates, except for those listed above. New dates are also welcomed for guided or private departures.


Guided: C 5795 (per person, double occupancy)

Includes 9 days, 8 nights, 8 breakfasts, 6 lunches, 6 dinners, guide and van support, maps and route instructions, luggage handling, hybrid bicycle rental, taxes.

Small groups or private tours, fully supported with drivers/guides and vehicles, all lodging and most meals included. Choose from existing dates or request new departures. Read more on our “What to Expect” page.

Self-Guided: C 5365 (per person, double occupancy)

Includes 9 days, 8 nights, 8 breakfasts, welcome briefing, maps and route instructions, inn to inn luggage transfers, essential transfers, hybrid bicycle rental, taxes.

Semi-supported, independent tours including welcome briefing, lodging, luggage transfers and necessary vehicle transfers. Choose from existing dates or request new departures. Read more on our “What to Expect” page.

Single Occupancy: 1345

Bike Rentals:

Hybrid-Fitness: Included

Upgrade to Road: 200

Upgrade to E-bike: 250

All details and pricing are subject to change without notice.

Please see above for accurate pricing and inclusions, unless we have proposed a customized trip for you and those details are provided in your custom proposal.

1. Choose an advertised date to join a small group, or see our Join a Group page to see where groups are already forming.

2. Pick your own dates. We will confirm quickly, and are happy to talk with you as you make your choice. If you would like a private guided date, this usually comes at a surcharge depending on the details, please get in touch for more information. If you prefer self-guided, we usually only require two participants to initiate a new date at the advertised price, and can sometimes reduce prices for you if you have four or more.

PLEASE NOTE: Trip Cancellation Insurance is highly recommended. If this is not provided by your credit card or elsewhere, please let us know and we can provide recommendations.


The best time to enjoy this tour is April to September.

Spring, average temperatures range from 12.5 to 16.6 °C (54.6 to 61.9 °F) in April and May.

Summer,  June to August, can be quite hot, typically peaking around 25 °C (77 °F) but sometimes reaching over 30 °C (86 °F). Beaches and towns can be quite crowded during tourist season.

Autumn, is quite mild, with September temperatures averaging 20 °C (68 °F).


The largest nearby airports are Pisa International Airport (PSA) or Florence Airport (FLA).

Once in Italy, it is easiest to access the meeting location at Camuci-Cortona by trail. Fares and schedules from locations across Italy and the rest of Europe are at


Your tour concludes on the morning of day nine with a transfer to the train station at Talamone, or Orbetello Monte Argentario if you’re lodging at Porto Santo Stefano.


If you have one day:

Pisa – One of the original Italian maritime republics and an important Roman naval center near the mouth of the Arno River, Pisa is a delight to explore on foot. Spend a day visiting one of the many historic churches, the city’s famous leaning belltower or a medieval palace and stroll along the Arno. Despite heavy shelling during WWII, much of the grand architecture funded by Pisa’s wealthy merchant families remain the core fabric of Pisa’s city center. If you need lodging in Pisa, you might consider:

Florence – The birthplace of high Renaissance art, you can spend several days exploring the numerous museums, art galleries and architectural delights. Highlights include the Uffizi – perhaps the world’s finest collection of Italian and Renaissance art, walking along the banks of the Arno, crossing the Ponte Vecchio, experiencing Brunelleschi’s Dome, Giotto’s Bell Tower, and the abundance of visual, culinary, and cultural treasures this vibrant city offers.

We can suggest the following lodging options in Florence:

If you have several days:

Siena – One of Italy’s best-preserved medieval towns, Siena is located in the heart of Tuscany and a good place to spend a day or two before delving deeper into the Tuscan countryside. With a population of about 50,000, Siena is a lively town with several major churches and museums to explore and most of the old town is car free making it a delight to explore on foot. We recommend the following accommodations in Siena:

We recommend the following accommodations in Siena:

Extend your stay in Italy on another Freewheeling Adventure!

More Reading:

Tuscany straddles the Apennine hills in the heart of Italy, where cypress trees, olive groves, vineyards, and soft, verdant hills create a landscape reminiscent of Renaissance paintings. Giotto, Michelangelo, and Leonardo da Vinci traveled these same landscapes centuries ago, and fortunately, not much has changed. Their influence is evident in many towns and villages along the route, and as you ride quiet routes along sun-drenched ridges, you will enjoy expansive views over the landscape of their inspiration. If you can spare some extra time, we recommend that you plan to spend a day or more in Siena or Florence before or after your Freewheeling Adventure, to see the riches these ancient cities have on display.