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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
$3445
Price includes roundtrip airfare.
Land only
7 days from only
$2495
Pre-trip Extension:
Florence · 2 nights $295

Post-trip Extension:
Rome · 2 nights $345
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There is no mistaking the mesmerizing beauty of Tuscany.

Cypress-lined lanes lead us to magnificent medieval hill towns untouched by time. Endless vineyards produce some of the world’s finest vintages. And unspoiled valleys unfold for some of the most rewarding reels you’ll ever experience. Our routes connect you to its most cherished gems – San Gimignano, Siena, Pienza, Montepulciano – over spellbinding terrain. Off the saddle, we’ll meet the warm people at wine-tasting enotecas, gain Renaissance insight during a private lecture, and luxuriate in elegant accommodations, including a refurbished monastery in the heart of Siena that affords us evening and early-morning strolls in its medieval warrens.

What's Included

Bicycle Tour Only - without Air

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

No Hassle Air Package Plus

  • Roundtrip international airfare
  • 8 nights in 4-star historic hotels and one country villa
  • 13 meals - 8 breakfasts, 1 lunch, 4 dinners
  • Airport transfers
  • And the option to add our Low-Cost Trip Extensions: Pre-trip: Florence - 2 nights for only $295 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: Mod/Adv
  • Daily Mileage: 30-60 miles
  • Daily Bicycling Time: 3-6 hours
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