Part 4: Cycling Through History
After days absorbing the art and food of Rome and Florence it was time to join my usual biking pals for an organized bicycle tour through Chianti.
Our tour provider was Vermont Bike Tours (VBT). And, while I know there are other amazing bike tour companies out there, I can attest that VBT always furnishes skilled guides, high quality bikes, well curated hotels, great restaurants, and accurate wonderful turn-by-turn GPS routes. After 16 cycling tours with VBT all over planet earth, they have earned my confidence.
I just buy the land portion of the tours and book my own airfare. This allows me to tack on a week or two of independent travel on the front and/or back of each tour.
Our Chianti trip began with a shuttle to meet our guides. The guides for VBT are excellent and always make these complex tours flow seamlessly.
Our first stop was the village of Radda in Chianti. Here we began with a safety class, bike fitting, and a 15 mile warm-up ride to Castellina. The ride was followed by a welcome dinner in our hotel (Palazzo Leopoldo).
Radda in Chianti is one of the five hilltop villages in Chianti. Radda is tiny and offers some quaint shops (including a tiny, yet terrific, bike shop with lots jerseys).
In the morning we set out for 27 miles of cycling ride through some beautiful vineyards with a stop for a picnic lunch at the 11th century Castello di Meleto. At Castello di Meleto we spent time touring the castle and took a tour of their sustainable vineyards with their agricultural expert and organic bee keeper Gabriella. The stop gave us a perspective on the dynamic history of the region.
Vineyards at Castello di Meleto
The Castle is now a lovely bed and breakfast and boasts the only intact theater of its kind in the region.
Touring the Castello's Theater
Learning About the Wars for Regional Dominance Between Siena and Florence
After returning to Radda it was time to enjoy my appointment in the hotel's spa and later some amazing pizza for dinner.
Pizza Break (Radda in Chianti)
The next day was a transfer day. First we cycled through Castellina a town designed by Fillipo Bunelleschi (the genius who solved the design for the famous dome in Florence). He centered the roads into the middle of the village to protect its residents from attack.
The cycling took us through the fortified village of Monteriggioni with a stop in Lilliano.
A Rainy Day Pedaling Through Some Lovely Hilltowns
From here we shuttled to the walled city of Casale Marittimo (Where VBT photographed cyclists for the brochure). And here I found some pretty great gelato. I mean it is Italy......
Casale Marittimo
The final leg of our 24 miles of cycling was a zippy downhill run through vineyards to our next hotel located right on the Tyrrhenian Sea.
Arriving at the Beach
The evening was capped by a stop at the home of a local architect "Chicca". Here, she orchestrated a very lovely (and tasty) hands-on cooking class. We learned some Tuscan recipes, shared some love with her big fluffy dogs, and thoroughly enjoyed the food we cooked in her kitchen.
Roadboy's Travels © 2025
