Bicycling Chianti - Florence to Lucca

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.

 Chicca's Canine Welcome Committee

 

 Chiccca Teaching Some Tuscan Cooking Skills

 

Cheese and Honey Appetizers, Gnochi, and Dessert

 

The next day was spent riding in a lovely 27 mile ride along the elegant tree lined roads encircling many of the regions most premier vineyards.

 

Cycling Framed By Rows of Italian Cypress Trees 

 

Riding the Bolgherese Strada del Vino

 

At midday we stopped for a farm to table vegetarian lunch at the Fonte di Foiano olive mill. Our hosts explained the nuances of the olive oils produced in the region. A bottle of their award winning olive oil made its way into my suitcase for the journey home.

The next day was spent on a 42 mile ride through the ancient village of Suvereto. From there we cycled past coastal cypress lined roads, fields of artichoke and sunflowers, ending at the Hotel Caliderio. 

 

 Scenery Reminiscent of California's Monterey Coast 

 

The Caliderio hotel wraps itself around its specatcular 3000 Sq. meter Etruscan hot spring pool. Dinner was fish in Campaglia Marittima.

 

The next day was spent pedaling along Barrtti Bay with a stop at the ancient city of Populonia with its museum and watch tower. 

More Trees to Admire

Some Ceramics at Populonia

 

After returning to the hotel we swam, then all gathered to bid our guides farewell and have our final dinner. 

The next morning we shuttled to Lucca for a walking tour. I then went on to spend an evening on my own in Verona. Verona is lovely and boasts its own coliseum. This coliseum, despite being older than the Coliseum in Rome, is still in use. It was a perfect way to end my tour. 

 

Verona!

 

Up next, my series will chronicle my fall 2024 return to cycle in Greece.

 

Roadboy's Travels © 2025