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Exploring Tuscany on Two Wheels: A 6-Day Bike Tour Challenge

  • Writer: Ruth Bergman
    Ruth Bergman
  • Jan 19
  • 7 min read

Updated: Mar 21

Intoduction

"We're biking in Tuscany," Oren said to me in October 2019 as we pulled away from Pienza on the first day of our biking adventure. If you're a biking aficionado and follow pro bike tours, you may share this sentiment. I have always enjoyed biking much more than watching others bike. However, I could certainly get excited about being in Tuscany, which is renowned for its great food, exquisite wine, and some of the most picturesque scenery on the planet. Biking offers several advantages in this setting over driving. The distances are suitable for biking, allowing you to proceed at a leisurely pace and stop at every vineyard for photos. You can indulge in food and drink without guilt, and after a day's ride, the meals taste even better. Wine tasting while riding, however, is not recommended.

Oren selected our tour company, Cicloposse, based on the quality of the bikes they rent. Naturally, we opted for the Challenge Tuscany tour, which covers about 70 km per day and plenty of hills. I was fit, but I wasn’t biking regularly. We decided that we should be able to manage the distance, going slowly if needed. While this is true, we didn’t consider the cumulative strain of biking such distances day after day. Nevertheless, we went for it, and there are no regrets.

The ride is stunning. As you navigate each bend and crest each hill, green vinyards, sown fields, rolling hills, and historic towns reveal themselves. Every meal becomes a memorable experience, offering local dishes crafted with precise attention and delightful flavors.

Day 1: Pienza & Montepulciano

Day 2: Montalcino & Orcia Valley

Day 3: Gorgonoza Castle via Trequanda and Lucignano

Day 4: Gorgonzola to Castelina

Day 5: Onto San Gimignano

Day 6: Loop around San Gimignano

Final Thoughts

Cycling Route Maps

Resources







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