Chianti: Where Cycling Dreams Meet Wine-Filled Hills

If you read my last post about Florence, you’ll remember the plan: something for me, something for Hubby, and something the kids wouldn’t roll their eyes at. Hubby, in particular, has been fixated on L’Eroica, the legendary vintage bike race held every October in Gaiole in Chianti, ever since cycling became his hobby of choice. So with him in mind, I booked our Airbnb right in the heart of Chianti — he’d get his day of living the two-wheeled dream, while the kids and I explored what might be the most postcard-perfect region in all of Italy. Win-win.

Chianti: A Mood, Not Just a Region

Picture rolling hills bathed in golden light, vineyards stretching to the horizon, olive groves shimmering in the breeze, and medieval towns perched on hilltops like they’ve been frozen in time. It’s no wonder this corner of Tuscany is one of the most beloved destinations in the country — and no, I’m not exaggerating for blog effect. It really is that pretty.

Things to Do in Chianti (Besides Dining at Every Opportunity)

Visit wineries. Chianti and wine are basically inseparable — visiting one here isn’t just an activity, it’s a rite of passage. From Chianti Classico to bold Super Tuscans, tastings usually come with generous pours, a peek into centuries-old cellars, and stories told with that warm Italian charm that makes you forget you’re on your fourth glass.

Explore the countryside. Drive, hike, or cycle (Hubby’s favorite, obviously). However you get around, every turn reveals cypress-lined roads, endless vineyards, and farmhouses that look lifted straight out of a Renaissance painting.

Wander the historic towns. Greve in Chianti is the bustling heart, with its charming Piazza Matteotti; Radda has narrow medieval alleys and sweeping vineyard views; Castellina is full of hidden courtyards and trattorias; and Gaiole shares its postcard frame between castles and vineyards.

Catch a festival, if the timing lines up. The Chianti Classico Wine Festival runs in September, and the whimsical Mercantia Street Theatre Festival takes over in July. Both are less “tourist event” and more a genuine peek into Tuscany’s soul.

Visit castles and abbeys. The imposing Castello di Brolio (vineyards plus fairytale vibes) and the serene Badia a Coltibuono abbey both tell the story of Chianti’s noble past.

Relax in thermal baths. Once you’ve had your fill of wine and wandering, sink into the waters of Rapolano Terme or Bagno Vignoni. Spa day, Tuscan style.

I was hooked on Chianti before we’d even left home, just from scrolling through photos and blogs. The next step was figuring out where, exactly, to base ourselves.

Visit Wineries
Chianti and wine are basically inseparable. Visiting wineries here is not just an activity—it’s a rite of passage. From Chianti Classico to bold Super Tuscans, tastings usually come with generous pours, a peek into centuries-old wine cellars, and stories told with that warm Italian charm.

Explore the Countryside
Drive, hike, or cycle (Hubby’s favorite, obviously). No matter how you get around, every turn reveals a new jaw-dropping view: cypress-lined roads, endless vineyards, and farmhouses straight out of a Renaissance painting.

Wander Historic Towns
Chianti’s small towns feel like stepping into a living history book. Greve in Chianti, the bustling heart with its charming Piazza Matteotti; Radda, with its narrow medieval alleys and sweeping vineyard views; Castellina, full of hidden courtyards and trattorias; and Gaiole, where castles and vineyards share the same postcard-perfect frame.

Festivals & Events
If you’re lucky with timing, you might stumble into the Chianti Classico Wine Festival in September or the whimsical Mercantia Street Theatre Festival in July. These celebrations aren’t just fun—they’re a peek into Tuscany’s soul.

Visit Castles & Abbeys
From the imposing Castello di Brolio (think vineyards plus fairytale vibes) to the serene Badia a Coltibuono abbey, these places tell the story of Chianti’s noble past.

Relax in Thermal Baths
When you’ve had your fill of wine and wandering, sink into the healing waters of Rapolano Terme or Bagno Vignoni. Spa day, Tuscan style.

I was hooked on Chianti before we’d even left home, just from scrolling through photos and blogs. The next step was figuring out where, exactly, to base ourselves.

Chianti’s Towns, at a Glance

Chianti isn’t one town — it’s a scattering of them, each with its own personality:

• Greve in Chianti – the largest, known for its lively weekly market and cafés ringing Piazza Matteotti.
• Radda in Chianti – a tiny hilltop gem, all medieval charm and quiet alleys.
• Castellina in Chianti – ideal for strolling, shopping, and long Tuscan lunches.
• Gaiole in Chianti – cycling central, surrounded by castles and vineyards (and L’Eroica territory).
• San Casciano in Val di Pesa – just outside Florence, all scenic countryside and beautiful churches.
• Panzano in Chianti – a hilltop haven with the kind of views that make you stop mid-sentence.

I set my heart on Panzano for one simple reason: Tuscan summers are hot, and hilltop towns run just that little bit cooler — and breezier for evening strolls. It also isn’t too remote to reach without a car, which, as it turned out, mattered more than I expected.

How to Get to Chianti’s Towns from Florence

A quick and important update if you’re planning based on an old blog post (mine included — I had to fix this myself): the bus company everyone remembers as SITA hasn’t existed since 2021. Regional buses across Tuscany, including all the routes into Chianti, are now run by a single operator, Autolinee Toscane — timetables and tickets are on at-bus.it. Locals still call it “SITA” out of habit, so don’t be thrown off if someone gives you directions the old-fashioned way.

Here’s the honest rundown, town by town:

Greve in Chianti and Panzano are the easiest to reach without a car. Line 365 runs directly from Florence’s Autostazione (near Santa Maria Novella station) to Greve in roughly an hour, with several services continuing on to Panzano in about 1 hour 15 minutes. This is the route we took, and it’s genuinely simple — no transfers, no guesswork.

San Casciano in Val di Pesa is even more straightforward, being the closest town to Florence. Several Autolinee Toscane lines (367, 368, 370, 371) connect it to the city in well under an hour.

Castellina in Chianti is where things get trickier. There’s no direct bus from Florence — line 365 only gets you as far as Greve, and from there you’re looking at a transfer (or a change via Siena) that can stretch the trip to two hours or more. If Castellina is your base, I’d genuinely recommend renting a car or arranging a private transfer instead of fighting the timetable.

Radda in Chianti and Gaiole in Chianti are the most remote of the bunch, and public transport reflects that. There’s no direct bus from Florence to either — you’re generally routed through Siena or via a connecting bus at Tondo Lucarelli, and the whole journey can take upwards of two hours each way, with limited daily departures. Driving cuts this down to under an hour. If you’re chasing L’Eroica in Gaiole like Hubby was, budget the extra travel time or plan to hire a car for that leg specifically.

The short version: if your itinerary is Florence, Greve, and Panzano, buses will treat you fine. If Radda, Gaiole, or Castellina are on your list, a rental car (or at least a car for that day) will save you hours of your holiday you’d rather spend at a vineyard.

Getting to Panzano, Our Home Base

As you’ll recall from my last post, our plan to rent a car the moment we landed in Florence fell apart when Hubby had to fly back for work. Silver lining: our Panzano Airbnb was reachable by bus, and our host even picked us up right at the stop — no dragging suitcases up a hill required.

After we’d had our fill of Florence, we boarded the bus to Panzano. It’s a smooth, roughly hour-long ride that winds through Chianti’s famous hills, past vineyards that look like they’ve been styled for a postcard. By the time we arrived, I was already in love — and I hadn’t even had a glass of wine yet.

Our Home in the Hills

Our Airbnb was everything I imagined a Tuscan home would be: rustic charm, a sun-dappled garden, and a backyard with a vineyard view. Best part? Achita had her own slide and swings, plus a treasure trove of dolls and toys — a Tuscan villa with built-in babysitting entertainment. Dreamy. The only hiccup was the upstairs bedroom getting warm in the afternoons, but our lovely host Rosalba sorted us out with a fan, and we were comfortable again.

Evening in Panzano

After settling in, we strolled down to the town square in search of the famous Dario Cecchini restaurant, on our host’s recommendation. Dinner, we quickly learned, doesn’t start until 8pm — Italians take “late dining” to another level. So we wandered the quiet streets, soaking in Panzano’s golden hour glow, and even stumbled on a perfect photo spot near the bus stop, because apparently in Tuscany even the waiting areas are photogenic.

Dining at Dario Cecchini’s

Dinner at Dario’s wasn’t just a meal — it was an experience. Think all-you-can-eat meat served family-style at long communal tables, where strangers become dinner companions and every course feels like a small festival.

The meat itself was juicy, tender, and thoroughly melt-in-your-mouth. Even little Achita approved, happily nibbling away, while Fabio — with his bottomless appetite — declared it one of the best meals of his life. As for me, I tapped out after the third course, happily defeated by a perfectly cooked steak.

We didn’t fully register how famous Dario Cecchini was until later — apparently his name is legendary in the culinary world, and we’d somehow scored seats without a reservation. Pure beginner’s luck; I wouldn’t count on it twice. These days the restaurant (officially rebranded Officina Cecchini, formerly known as Officina della Bistecca) runs a single evening seating around 7:30–8pm with a fixed set menu built around Bistecca alla Fiorentina, and bookings are taken by phone or email — worth locking in weeks ahead, especially in summer, rather than hoping for our kind of luck.

By the time dinner ended after 10pm, we were stuffed, smiling, and rolling ourselves back up the hill. Achita was fast asleep in her stroller, and the night air was cool and quiet. It was the perfect ending to a long Tuscan day, wrapped up in one unforgettable meal. ❤️

Spotlight: Who is Dario Cecchini?

If Tuscany had a Meat Maestro, it would be Dario Cecchini. Born and raised in Panzano, he’s an eighth-generation butcher who turned a family trade going back roughly two centuries into a full culinary empire. He’s been featured in countless documentaries and TV appearances — including Netflix’s Chef’s Table — and his booming personality is almost as legendary as his steaks.

Dining at his restaurants in Panzano isn’t just about eating, it’s a celebration: communal tables, course after course of perfectly cooked meat, and an atmosphere somewhere between feast and theatre. No pretension, no fussy menus, just pure carnivore joy.

Tip: Reservations are essentially a must these days (we got in by sheer luck — don’t count on repeating that). If you’re a meat lover, this is your Tuscan pilgrimage.

Next up: our days based in Panzano, Hubby’s L’Eroica pilgrimage, and the day trips that took us deeper into Chianti’s hills.