Day by Day Itinerary

Italy: Tuscany Bike

Countries   Italy
Tour Length   8 days
Dates Of Tour   Sunday, April 27, 2014
Saturday, May 24, 2014
Sunday, June 15, 2014
Sunday, September 14, 2014
(Self-guided adventures can be requested any time.)
Type of Tour Road (Guided, Self-Guided)
Price $3,465 (Self-Guided - US $3295)
Family Friendly
Age of Participants Mixed
Gender Basis Mixed
# of Participants (max) 12
Language English, Italian
Sleeping Accommodations   
Luggage Support
Sag Wagon Along the Way
Meals Provided Full board
Total Trip Mileage    235 Miles
Average Daily Mileage    47 Miles Per Day
Longest Single Day 52 Miles
Overall Difficulty Rating   Intermediate, Advanced
Cost of Trip without Airfare per person  $3,465
Single Supplement $935
  • 8 days
  • 7 nights
  • 7 breakfasts
  • 5 picnic lunches
  • 4 dinners
  • snacks
  • guide and van support
  • maps and route notes
  • luggage handling
  • taxes
  • local olive oil
  • beautiful valleys
  • ancient villages
  • exquisite cuisine
  • fresh produce
  • Roman baths
  • Gregorian chants
  • olive orchards
  • piazzias
  • cafes and expressos

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. Beginning near Florence with a pickup at Poggibonsi or Siena, you will spend the first two nights in spectacular San Gimignano, famous for its abundance of stone towers.

You will then cross the Chiantigiana route through the premier wine region of Chianti. On your way toward the hills of Southern Tuscany, you will have ample opportunity to sample wine, honey and olive oil, as well as being fuelled by the gastronomic indulgence of some of the region’s finest chefs. You will repose in small inns known for their character and charm, and will fall, if you have not already done so, in love with the area which D.H. Lawrence referred to as "the perfect center of man's universe". After visiting Montepulciano and Montalcino, tasting what are perhaps Italy's most complex wines - the Vino Nobile and Brunello di Montalcino, and stopping to listen to the Gregorian monks chanting in an awe-inspiring cathedral, you will enjoy the evening ambience of your peaceful hotel in Pienza. 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.

Day 1   Greetings and Dinner
Day 2   Ride one of three loop options (30, 52, or 62km/19, 33, or 40 miles) from San Gimignano.
Day 3   An exhilarating 50 km/32 mile through forest and field on some of the least traveled roads in the re
Day 4   65km loop ride
Day 5   84km/53 miles.
Day 6   62km/40 miles.
Day 7   72km/45 miles.
Day 8   Farewells.
Countries Visited  
  • Italy
    • Tuscany
Discounts forReturning Customers and Referals

If you have been on tour with us in the last 3 years, you will receive a 5% discount as a returning guest. In addition, if you have referred new customers to us since your last Freewheeling Adventure, you are entitled to a reduced cost. Each new guest who mentioned you as a referrer will save you $125 off your next trip.


• Cost: US $3095 C$3295 (per person, includes 8 days, 7 nights, 7 breakfasts, maps & route notes, luggage transfers, 2 people transfers, taxes)
• Self-guided adventures can be requested any time.


Hybrid $225 or Racing $395


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.

Company Name Freewheeling Adventures
Country     Canada
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