Tuscany

There’s a good reason Tuscany is one of the most romanticized destinations in the world—it truly is a magical place to explore by bicycle. Especially in May, when the countryside is at its very best: rolling hills are painted in vibrant shades of green, wildflowers bloom along the roadsides, and the air is fresh and fragrant before the summer heat and crowds arrive. Tuscany’s terrain is wonderfully engaging without being overwhelming—constantly changing, gently challenging, and endlessly beautiful. It’s the kind of riding that keeps you smiling all day long.

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The tour begins in Lucca, one of my favorite towns in all of Italy, renowned for its perfectly preserved Renaissance walls, elegant tree-lined promenades, and lively piazzas. From Lucca, we head south on quiet backroads and sections of Tuscany’s iconic Strade Bianche—the white gravel roads that wind through vineyards, olive groves, and cypress-lined hills. Our first stop is the hilltop town of Volterra, rich in Etruscan history and dramatic views, before continuing on to longer stays in Siena and Pienza. These days allow us to truly settle in, enjoy the towns, and take in the surrounding countryside at a relaxed pace. From there, we loop back north through the storied wine region of Chianti, where rolling vineyards and medieval villages define the landscape.

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Along the way, we’ll experience four UNESCO World Heritage Sites—Val d’Orcia, Siena, San Gimignano, and Pienza—each offering its own unique blend of history, architecture, and scenery. Of course, no journey through Tuscany would be complete without savoring the region’s exceptional food and wine: long, convivial dinners featuring local specialties, simple ingredients done beautifully, and wines that perfectly reflect the land they come from.

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Tour Facts:

  • Dates: May 3- May 15, 2026

  • Arrival/ departure city: Florence, Italy. Or Pisa, Italy. Transfer to Lucca not included.

  • Price: $3300

  • Included: 12 nights lodging, all breakfasts, 10 dinners, ride snacks, and luggage transfer.

  • To reserve your spot please email info@velowild.com

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