The wine festival worth planning your trip around
- Nigel Jeacock-Fewtrell
- Aug 11
- 3 min read
A guest blog, by Nigel Jeacock-Fewtrell
We've stayed at Casalone in Chianti several times now, and every visit reminds us why we keep coming back. The location is simply perfect. Whether you enjoy walking, cycling, exploring hilltop villages or, as we discovered last September, spending an evening at Chianti’s largest wine event, everything is within easy reach.
Expo Chianti Classico: an unmissable wine festival
One of the highlights of our stay was Expo Chianti Classico, the wine festival held in Greve in Chianti every September. Running over four days, it brings together wine tastings, local produce to sample, olive oil tasting, live music, art exhibitions and even fashion shows. We'd heard good things — but it exceeded every expectation.
We walked down in the early evening and arranged with a local taxi driver to collect us when we were ready. This meant we could fully relax, enjoy the wines and soak up the atmosphere without worrying about the drive home.
The historic piazza in Greve is packed with stalls for the occasion. For €20 you're given a wine glass in a protective shoulder sling — very practical — plus a tasting card good for seven pours (although in practice, no one we encountered seemed too strict about counting and we were positively encouraged to taste as much as we wanted).
With more than 60 producers exhibiting, the choice is extraordinary. Whether you're already a Chianti Classico devotee or simply curious, you'll find plenty of wines worth taking home — organic, delicious, and full of character. What struck us most was the producers themselves: endlessly knowledgeable, genuinely passionate, and happy to talk through grape varieties and winemaking techniques without ever making it feel intimidating. We learned more chatting with them than we could have from any guidebook. Complimentary snacks along the way helped us pace ourselves through a very agreeable few hours before we had dinner and enjoyed the live band that weaved its way among the tables.
The whole town comes alive for the festival, buzzing with locals and visitors alike. One tip: if you're planning to eat in Greve, book your restaurant in advance — it's a major date in the local calendar.
For details of each year's event, visit the Expo del Chianti Classico website.
Raising wine glasses at opening ceremony Live music at the festival An Expo del Chianti Classico wine glass Traditional costume at the Expo parade Protective sleeve for your wine glass Local musicians at the festival
Images courtesy of Expo del Chianti Classico. Stills from video by SwollyStudio.
Other activities to enjoy in September
Exploring Chianti by bike
Part of what makes Casalone such a wonderful base is how much there is to do nearby. On another day we hired e-bikes from Officina Ramuzzi in Greve. The team there were as helpful as they were charming. Armed with a map and a recommended route, we cycled around 40km at an easy pace, stopping for a fantastic lunch along the way. With an e-bike, Tuscany's hills become part of the fun rather than a challenge, leaving you free to take in the vineyards, olive groves, ancient villages and glorious views. Genuinely one of the best days we've ever had anywhere.
Beautiful walks straight from Casalone
Some of our favourite moments were the simplest: setting off on foot directly from the farmhouse. Using a walking app to find local trails, we discovered wonderful routes through woodland, vineyards and quiet country lanes - often without seeing another soul for miles.
That's the real beauty of staying at Casalone: you can leave the car behind and let Tuscany unfold at its own pace. The pretty village of Montefioralle is within walking distance (where we've enjoyed memorable meals with equally memorable views) and closer still, there are vineyards offering tastings and snacks almost on the doorstep.
Our recommendation
Whether you're drawn by the wine festival, a cycling adventure, or peaceful walks through the Chianti countryside, Casalone is the perfect base for exploring this beautiful area at a slower pace. We'll certainly be back again.
If you time your visit for September you can enjoy the benefits of cooler days for outdoor activities and there are wine festivals throughout the month (Montefioralle has its own smaller event later in September). The icing on the cake is that it's still warm enough to enjoy Casalone's magnificent swimming pool. It was an unforgettable stay, and a reminder of how much this region has to offer.
A huge thank you to Nigel for his entry into our journal. If you have recommendations you'd like to share we'd love to hear from you. Please get in touch with Barclay, barclay@casaloneinchianti.it.
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