Charnes Tours Logo
Toll Free:  1-888-491-2760

Guided Southern Tuscany Bike Tour

Guided Southern Tuscany Bike Tour
Southern Tuscany looks different from other parts of the region. This area is made up of endless rolling hills covered with grain fields, sunflowers, and vineyards. It is a rich green valley that stretches from the town of Siena south to a mountain called Amiata. Centuries ago Renaissance painters were drawn to these verdant hills. Today the best photographs of Tuscany are taken here. This bike tour starts in the Val d’Orcia, a river valley known for its hill towns, wine, and thermal waters. We spend two nights in Montalcino, a walled town set high on a hill punctuated with the spires of medieval buildings and an imposing castle. This town is home to one of Italy’s most prestigious wines, the Brunello di Montalcino. To learn more, we tour the winery where Brunello was first created. We soak in the soothing thermal waters of Bagno Vignoni, a Tuscan spa. We stay in the perfectly preserved Renaissance town of Pienza. We overnight in Montepulciano, a Renaissance gem built high on a volcanic ridge. The tour concludes in Cortona, a town nestled high on green mountainside above terraced olive groves.
Day 1 and 2 Montalcino  We meet in Florence and shuttle to Montalcino. A warm-up ride leads to the Biondi Santi winery, an old estate where the sublime Brunello wine was first produced. We tour the winery and sample their prestigious reds. We dine on traditional Tuscan cuisine at a warm family-run restaurant. On Day 2 we ride to a country inn for a hands-on cooking class. We visit Tuscany’s prettiest Romanesque church and top the day off with a guided wine tasting in a walled castle.

Day 3 and 4 Pienza  The road to Pienza passes through a village called Bagno Vignoni. The hot mineral waters of Bagno Vignoni have been drawing travelers since Roman times. Before lunch we test the curative powers of these natural waters. After lunch it is off to Pienza, an architectural wonder. Pienza was built at the behest of Pope who razed his hometown to build the perfect Humanist Renaissance town. The buildings, the piazzas, and the streets have been perfectly preserved. This part of Tuscany is known for its cheeses. On Day 3 we ride to a cheese farm where 700 free-range sheep do their part to produce a delicate local cheese called pecorino. Pecorino is made with full-fat ewe’s milk. The cheese can be soft and fresh, or firm and flavorful, depending on aging.

Day 5 Montepulciano  We cycle to Montepulciano, Tuscany’s highest hill town. Montepulciano is a town of rare beauty full of elegant Renaissance palaces, ancient churches, and charming squares. Its lofty location makes for vast panoramas over the wonderful valleys below. Centuries ago wine makers carved cantinas into the soft volcanic stone. To learn more about the Vino Nobile di Montepulciano do a winery tour.

Day 6 Cortona  Our last ride takes us through rolling farmland to the ancient town of Cortona. The city, enclosed by stone walls, sits on the top of a hill some 600 meters (2,000 feet) above sea level. This dominant position creates spectacular vistas. You can see all the way to Trasimeno Lake. Cortona is a mix of medieval, Renaissance and Baroque architecture. The streets are narrow, sometimes steep, drawing you through attractive shopping thoroughfares to the main square. Despite the fame it found through the book and movie, Under a Tuscan Sun, Cortona has retained a genuine, untouristy feel.

Day 7 Shuttle to Florence  Shuttle to Florence. On the way back to Florence we stop at the Badia a Coltibuono, an estate in Chianti. We have lunch at the Badia’s exceptional restaurant (including in the tour price).

Reserve This Tour Detailed Itinerary

US$ 3,245 per person
(US$ 550 Single Supplement)

Tour prices are based on double room occupancy. A single supplement is required for single room occupancy. Please note that in Italy single rooms are frequently smaller than double rooms. Groups of three can book triple rooms and avoid the single supplement.

2019 Date

7 Days, 6 Nights
Route Rating
Moderate: 10-30 miles (15-50 km) per day cycling over hilly terrain.

Meet / Finish
Florence / Florence
  • Cooking class
  • Brunello winery tour
  • Thermal spa visit
  • Cheese farm visit
  • Wine tasting in castle
  • 5 spectacular rides

What's Included
  • All lodging (3 and 4 star hotels)
  • All breakfasts
  • Two dinners
  • One cooking class
  • One picnic
  • Winery tour
  • Cheese farm tour
  • Guided wine tasting
  • Lunch on last day
  • Van transfer from Florence on Day 1
  • Van transfer to Florence on Day 7
  • 5 beautiful rides
  • Use of bike
  • Van support
  • Two guides

Cancellations: Terms and Conditions

Tour Summary
Map and Distances

Wineries and Castles
Dates don't work?
Consider one of our self-guided bike trips. We can schedule a self-guided bike tour whenever you want March 1 to October 31.

Have a group of four or more?
With a group of four or more we can schedule a guided bike tour when you want.