Cycling through Tuscany with my BFF: diary + pics from a week of fun!

When my longtime friend and fellow cyclist (well she's beyond a cyclist and is a superhuman triathlete/Iron Woman!! 🏆) invited me to embark on a week-long gravel tour through the Italian Tuscan countryside, I immediately agreed!! Cycling for a week and unlimited post-ride pasta and Chianti? Alongside Bobbie? What could possibly be better?! I was invited also because of my photography skills - I would be the official trip photog for the week, yay!!

The Tuscany Gravel Trip was operated by the amazing team at Thomson Bike Tours.

So how was it? Well, Tuscany feels like it was made for gravel riding. Its legendary strade bianche—those iconic white gravel roads—are a dream for any cyclist. Starting just outside the charming city of Siena, we pedaled through a landscape straight out of a painting: rolling hills, winding farm roads, and cypress-lined driveways leading to hilltop villas. Along the way, we explored the storybook medieval towns of Monteriggioni and San Gimignano, and rode past endless rows of Chianti and Vernaccia vineyards, with the Crete Senesi unfolding in front of us in all its Tuscan glory. It’s no wonder the Eroica and the world‑famous Strade Bianche race have put these roads on every cyclist’s dream list—riding them in person feels like pedaling through living history.

We had a great group along for the week - riders from California, Colorado, the East Coast. Was nice getting to know everyone and sharing the highs and lows of each ride. We had beautiful new Specialized gravel bikes and waking up each morning with a perfectly clean, perfectly pumped and well-tuned machine was such a bonus!

Speak of, huge shout out to all the guides and support staff at Thomson! They were all SO nice and friendly and supportive...to have cheerleaders along the way really helped. Thank you all!

But for me, the best part of this week even more special was sharing it with Bobbie. We have been friends since 2012 when we met living in Paris, and have never lost touch. She's a huge inspiration to me and I love how much fun we always have when together. Cannot wiat for the next adventure with my Billy Ray! ;)

There was something magical about cycling with Bobbie in Tuscany—we fell into an easy rhythm of pedalling, chatting, and sometimes just riding in silence, soaking in the views and trying to make the 13th climb of the day - at 18% grade - without crying, haha! Bobbie also liked to sing songs her daughters are currently into...Chicken Banana...huh?!

We laughed through the dusty climbs, cheered each other on, and stopped to admire the kind of vistas that make you forget how hard your legs are working. Every turn felt like a scene from a storybook: quiet farmhouses, golden light on the hills, and that sense of timeless adventure that keeps you coming back for “just one more kilometer.” By the end, we were tired, dusty, and so very happy—the kind of ride that lingers in your memory long after you’ve unclipped. Gelato was also a very highly anticipated post-ride recovery snack!

Mileage and elevation gains were no joke here either. We had an A Group and B Group. Most days I kept up with the A Group, but by the last day I wanted to just roll rather than push like mad all day.

The most challenging logistic of the week was laundry! Our hotels had no laundry facilities for guests and turnaround was 2 days if the hotel did it. So we washed clothes in the shower and hung on towel racks to dry. The towel rack in our room didn't heat up, so we used one of the other guests'. My cycling shoes got totally drenched one day riding in rain - and they never really fully dried out. Had to was on a very HOT cycle when I got back home!

What a wonderful week we shared - I would go back again in a heartbeat! Rides like this remind me why I fell in love with cycling in the first place. It’s not just about the miles or the climbs—it’s about the stories the road tells. Tuscany’s gravel paths felt like chapters in a book: some challenging, some serene, all unforgettable. Sharing the adventure with Bobbie made it even sweeter, turning each hill, each dusty turn, into a memory I’ll carry with me forever. If there’s one thing cycling has taught me, it’s that the best journeys aren’t just about reaching the destination—they’re about the moments in between, the laughter, the quiet, and the beauty that unfolds when you simply keep pedaling.

What a ride!! Thank you Bobbie & Thomson!!

xx

Lindsey