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Biking Vacation Tuscan Hill Towns by Bike​

Activity Level: Moderate/Advanced  |  Daily Mileage: 30 – 60 mi  |  Daily Biking: 3 – 6 hr
Air package plus
10 days from only
$3745
Price includes roundtrip airfare.
Land only
7 days from only
$2545
Pre-trip Extension:
Florence · 2 nights $345

Post-trip Extension:
Rome · 2 nights $345
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Two “must-see” medieval masterpieces of TuscanySan Gimignano and Sienaare only two of the gems that await you on this delightful cycling adventure.

You’ll say in converted monasteries and visit a church where horses are blessed … discover the source of Italy’s famous red wines in Chianti and Montepulciano … view stunningly detailed frescoes of a 14th-century abbey … and so much more. Exclusive VBT extras like an Italian language lesson, a lecture by a local art historian, and a wine tasting at a famous
enoteca ensure that you’ll go beyond the historic landmarks and beautiful scenery to discover the true essence of Tuscany. 

What's Included

Bicycle Tour Only – without Air

  • 6 nights in 4-star historic hotels and one country villa
  • 10 meals – 6 breakfasts, 1 lunch, 3 dinners

Air Package Plus

  • Roundtrip international airfare
  • 8 nights in 4-star historic hotels and one country villa
  • 12 meals – 8 breakfasts, 1 lunch, 3 dinners
  • Airport transfers
  • And the option to add our Low-Cost Trip Extensions: Pre-trip: Florence – 2 nights for only $345  Post-trip: Rome – 2 nights for only $345

Both Vacation Options Include

  • Free use of our custom VBT bicycle and helmet
  • Service of two bilingual VBT Trip Leaders
  • FULL VAN SUPPORT
  • Daily route directions and maps
  • Welcome reception with local wine and hors d'oeuvres
  • Sightseeing and cultural activities
  • 5% Frequent Traveler Credit to use on your next VBT vacation
  • Special Good Buy Discount

Cultural Highlights

  • Admire handcrafted crystal in Colle Val d'Elsa
  • Explore romantic San Gimignano, with its 13 medieval towers and idyllic plazas
  • Learn about the Italian Renaissance and the history of Siena in a lecture by a local historian
  • Visit the abbey of Monte Oliveto Maggiore, dating to 1313
  • Enjoy an included language workshop with your native Italian VBT Trip Leaders
  • View the beautiful hills surrounding Pienza from the terrace of our historic Hotel Il Chiostro

What to Expect

This tour offers the full range of easy terrain mixed with moderate and challenging hills. Our VBT van support shuttle is always available for those who need assistance with the hills. Ideal for more experienced cyclist.
  • Activity Level: Moderate/Advanced
  • Average Daily Mileage: 30 – 60 miles
  • Average Daily Cycling Time: 3 – 6 hours
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