Siena, Italy: a gorgeous hilltop city wrapped in medieval walls, flanked by Tuscan hills, and full of tradition. It’s like a smaller, more “authentic” Florence—meaning fewer tourists, more local flair, and (for better or worse) deeper immersion into Italian life. That immersion? It wore us out a bit. Yes, I know—cue the world’s tiniest violin for the travelers on week three of a dream Tuscany trip complaining about too much Italy. But hey, we’re just keeping it real.
Like the rolling landscape, this week in Siena came with its ups and downs:
The Ups:
Two-night escape to Cinque Terre: Needed it, loved it.
Caught the Giro d’Italia Stage 9 finish in Siena: Cycling fanboy heaven.
Pretty decent weather: A win, especially after soggy Portugal.
Day trip to San Gimignano: Pure Tuscan charm.
Countryside bike ride: Romantic and scenic.
The Downs:
No rental car: Forgot my International Driver’s Permit. Italy says “no permit, no car.” Portugal and Florence didn’t seem to care. Siena did.
Italian food burnout: Yep, it’s possible. Siena wasn’t helping—limited variety beyond the usual pasta-pizza parade.
Getting around sucked: No Uber, no Bolt, and taxis were scarce.
Travel day to Istanbul was a mess: (More on that in the next post.)
Locals felt a bit… indifferent: Not rude, just not super welcoming.
Still battling a stomach bug: Probably from suspect water back in Florence. Rookie move.
The Cinque Terre Detour
On a whim (thanks to a suggestion on this platform Ena), we booked a last-minute trip to Cinque Terre. If you don’t know it, it’s five jaw dropping pretty villages along the northwest coast of Italy, linked by train and hiking trails. Each has its own vibe, all photogenic as hell. We stayed in Monterosso—beach town, lemon festival, instant mood booster. I spent a day recovering while Tara soaked it all in. Access to both the beach and hikes? Jackpot.
The downside? Tourists—so many of us. The towns are tiny, and the train system just keeps funneling more in. But hey, we stayed for two nights, which obviously makes us better tourists than the day-trippers (right?). Still, the crowds were manageable this early in the season. Come summer? Total madness. We could’ve easily stayed another day or two.
San Gimignano: Worth It
Another day, another charming Tuscan town. San Gimignano was a highlight: car-free, scenic, and effortlessly elegant. Walking its streets, wine in hand, with panoramic views—this is what travel dreams are made of.
The Giro Comes to Town
The Giro d’Italia—a three-week cycling beast—ended Stage 9 right in Siena. I was in full fanboy mode. The region is famous for its “white roads” (Strade Bianche), gravel paths made from marble mining leftovers. Unlike the rocky dirt roads of Utah, these are smoother, historic, and iconic in the cycling world. Our Airbnb? Perfectly placed right before the final climb. Watching elite cyclists crush 100+ miles a day with 8,000+ feet of elevation? Unreal. These athletes are built different.
International Medical Update
Quick update for anyone interested in the international medical space, I found it extremely easy to have a tele-health Dr. consultation resulting in a prescription which then was filled at a local pharmacy. The pharmacy was quick to review the electronic prescription and sell the medication along with fielding any questions I had. The sunscreen was more expensive than the heavy drugs.
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Lessons from 10 Days in Tuscany:
Bring your International Driver’s Permit. Don’t be like me.
Yes, you can get tired of Italian food. Still couldn’t bring ourselves to eat at the local McDonald’s, though.
€10 for a sad sandwich? I’m frugal, not delusional.
Raw olives are disgusting. There’s a whole process to make them edible. Who knew?
Buses will be late. Plan accordingly.
Don’t drink sketchy water. Ever.
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Now we’re in Istanbul, staring out over the Bosphorus, surrounded by a sprawling, electric city. First impressions? It’s a hit. But more on that next time.
And no, I don’t have a Patreon for those of you asking :) (my Mom is probably the closest to it as she helps with logistics in Utah). But thanks for liking and subscribing… Kidding, we don’t care about that but hope you are gaining value from these posts.
Yaaas! So glad you both enjoyed it. Amazing, I stayed in Monterosso as well; during the lemon festival… also had a quick medical emergency that required hospital visit in Florence. I preferred Cinque Terre over the Almafi coast due to the combo of hiking + beaches.
Love the honesty about “Italian food burnout.” I hit that wall in Bologna of all places. There’s a hack for non-pasta cravings in places like Siena, but I’ll save it unless you’re desperate enough to need it