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No doubt you'll arrive with certain expectations of Tuscany and Umbria. But somehow the sensory feast is still a wonderful surprise. The sheer beauty of olive groves and vineyards. The slow pace of life. The symphony of flavors in traditional dishes. And the rich passione of the locals. Expectations exceeded? Just another day in the heart of Italy.

Umbria to Cortona, beneath the Tuscan Sun

  • Soak up the medieval ambience and ancient traditions of charming hilltop towns
  • Taste splendid wines, like sagrantino, Montefalco Rosso and Vino Nobile di Montepulciano
  • Delight in hearty ribollita, panzanella, fresh pastas and delicious pastries
  • Enjoy gracious hotels with distinct regional flavor
  • Get to know our favorite friends and colorful locals

Day 1-2
Ride tranquil bike paths flanked by bright red poppies, cypress trees and undulating hills. After soaking up beautiful views from Montefalco, savor a farm-to-table lunch in the Valle Umbra. Ride to timeless towns and sample fine vintages of velvety Sagrantino, Umbria's prize vino rosso. Experience warm Umbrian hospitality and hearty cuisine at a dinner in the countryside.

Days 3
Discover the ancient village of Spello en route to the World Heritage site of Assisi. Explore the historic sites of St. Francis's famed home. Find your inner Italian royalty as you experience a night in a true Umbrian castle, Castello di Monterone. Enjoy sweeping views of the Perugian countryside, where the produce for our gourmet meal is grown!

Days 4-5 
Welcome to Tuscany! Bike through the lush Val Niccone and the hills surrounding Montepulciano, revered for its 3,000-year-old Etruscan walls. Unwind at La Corte dei Papi, our enchanting hotel and a perennial favorite in the region. Visit historic hilltop Cortona, birthplace of many Renaissance artists and the setting for Under the Tuscan Sun. Taste splendid Tuscan wines, like Vino Nobile di Montepulciano, Brunello di Montalcino and Cortona's own rendition of syrah.

Days 6
Take a morning ride through the famous battlegrounds of Rome versus Carthage, biking through the colorful landscape of the border region between Tuscany and Umbria.

Contact us for pricing and availability.

Prices are based on double occupancy and are subject to availability. Airfare is not included.


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