Challenging
Difficulty level
Cycling
Activity (Bike)
6 Night, 7 Day
Duration

Italy: Tuscany Bike

Six nights; seven days of classic bicycle touring in the hills of Chianti and Southern Tuscany.

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



WHY THIS TRIP?

  • Rapolano Terme where the healing thermal baths of San Giovanni and terme Antica await.
  • the ancient village of Asciano to Rapolano Terme, stopping in Serre to see the Old Grange and Olive Oil Museum
  • visit large renaissance fresco paintings at the Abbazia di Monte Oliveto Maggiore, a large Benedictine monastery that was founded in 1320

 

ROUTE EXPECTATIONS:

The most challenging trips, these include longer distances, bigger hills, long hikes, exposed paddling, and full days of activity. We recommend a higher degree of fitness and training to make the most of the experience.


Most of the route is well paved, but there are a couple of short gravel stretches. There are lots of hills. This trip is best suited to experienced cyclists, and although relaxed riders are welcome to guided trips, they will require van support on longer climbs and distances.


Daily Distance:

  • DAY 1: Introductions
  • DAY 2: ~46 km or ~61 km
  • DAY 3: ~55 km
  • DAY 4: ~38 km
  • DAY 5: ~55 km
  • DAY 6: ~52 km
  • DAY 7: ~42 km & Farewells

Elevation Profile:

(Click image to enlarge)

 

Not sure about difficulties, and support level? Check out our What to Expect page!

 

Start: Siena train terminal 15:00, day one. Please contact us to arrange alternate plans.

Finish: Siena train terminal 14:00, day seven.

Please contact us to arrange alternate plans, if necessary.

1

Introductions

Meet at Siena late in the afternoon to experience what many believe to be Italy’s loveliest medieval city. Stroll along red brick lanes, visit the cathedral and art and history museums, and linger in the centuries-old Piazza del Campo before unwinding in your inn’s garden terrace. D (Meal inclusions provided for guided trips. Self-guided trips include breakfast only)

Albergo Chiusarelli, Siena

2

Monteriggioni Loop 46km or 62km

Enjoy a loop ride through the countryside surrounding Siena, including a visit to the fortified town of Monteriggioni. The ride today is predominantly paved but there are some gravel sections, and one significant climb of approximately 300 meters over 4 ½ km; a pleasant warm up ride for the days to come. Return to Siena with time for independent evening explorations. BL

Same lodging

3

Siena to Sant’Angelo in Colle 55km

Begin with some easy cycling, following paved and gravel roads from Siena through the Crete Senesi. The final 20km of the ride includes a steady climb as you skirt the cities of Buonconvento and Montalcino on your way to the village of Sant’Angelo in Colle. Today’s route takes you into the heart of Tuscany’s most well-known wine growing regions. You will cycle past vast vineyards of Sangiovese, which in Latin means, “the blood of Jupiter”; these grapes have been used in the Brunello di Montalcino since the 14th century. BLD

Castel Brunello, Sant’Angelo in Colle

4

Montalcino Loop 38km

A short loop ride through vineyards and countryside of the Val d’Orcia to Montalcino allows for an early stop at the Romanesque Abbey of Sant’Antimo. Set among ancient olive groves and fields of wheat, the resident Gregorian monks gather seven times a day to chant their prayers; they also produce a unique selection of artisanal tonics and tinctures available at their pharmacy. Continue to the medieval hilltop gem of Montalcino, a good spot to explore before lunch. The return ride to Sant’Angelo in Colle travels through oak forests and along ridge roads with vast views of the surrounding vineyards and fields. B

Same lodging

5

Sant’Angello in Colle to Rapolano Terme 55km

Ride north through the Senesi, passing Montalcino on your way to Rapolano Terme where the healing thermal baths of San Giovanni and terme Antica await. Along the way, visit large renaissance fresco paintings at the Abbazia di Monte Oliveto Maggiore, a large Benedictine monastery that was founded in 1320. Continue cycling through the ancient village of Asciano to Rapolano Terme, stopping in Serre to see the Old Grange and Olive Oil Museum. The thermal waters flowing from the springs at Rapolano have been easing sore muscles and stressed minds since Roman times. BLD

Castello delle Serre, or optional upgrade to Terme San Giovanni (Get in touch for details), Rapolano Terme

6

Rapolano to Radda in Chianti 52km

Today you will ride through the gentle hills and valleys of Il Chianti. This region is renowned for its olive groves and vineyards which produce some of Italy’s finest oils and wines, including the esteemed Classico easily identified by the iconic black rooster brand. Your route will take you past the historic Castello di Brolio, a huge medieval estate and home of the oldest winery in Italy. BLD

Relais Vignale, Radda in Chianti

7

Radda in Chianti to Siena 42km

Your final ride follows a mix of gravel and paved roads back to Siena where your tour concludes in the early afternoon. On the way, you’ll visit the monument at Montaperti, which signifies the site of Italy’s bloodiest medieval battle. It is now a peacefully, quiet place and provides an ideal backdrop to contemplate the past weeks escapades. You may choose to spend more time in Siena or proceed to Florence or other nearby destinations. BL

All details and pricing are subject to change without notice.


WHAT’S INCLUDED IN THE COST OF YOUR TRIP?

Not sure about difficulties, and support level? Check out our What to Expect page!

Guided: C 4295 (per person, double occupancy)

Includes 7 days, 6 nights, 6 breakfasts, 5 lunches, 4 dinners, guide and van support, maps and route instructions, luggage handling, taxes

Does not include bike rentals & single supplement charges (pricing can be found in next booking step), airfare to/from tour, and guide(s) gratuities.


Self-Guided: C 3295 (per person, double occupancy)

Includes 7 days, 6 nights, 6 breakfasts, maps, route instructins, inn to inn luggage transfers, essential transfers, taxes

Does not include bike rentals & single supplement charges (pricing can be found in next booking step), airfare to/from tour, and guide(s) gratuities.


All details and pricing are subject to change without notice.


2022 Guided dates:

  • May 22-28
  • Jun 5-11
  • Sep 25-Oct 1

2023 Guided dates:

  • May 21-27
  • Sep 24-30

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

Interested in custom or private departures?


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, price remains the same as advertised if you have at least six. 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. Please ask us for a no-obligation quote from our insurance providers: Century Insurance, or CSA Travel Protection.

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.