72 Hours In The Tuscan Countryside: Where to Explore, Eat, Sip & Unwind In The Heart Of Italy’s Wine Country

I have a confession to make. Controversially, I am not a city break gal. I know – the idea of hopping between buzzy cafés, museums and metro stops is a dream for many. But for me? I’m all citied out. After living in Sydney, Paris, Los Angeles and now London, I’ve had my fill of the hustle: the constant movement; the packed itineraries; the navigation battles. Don’t get me wrong – cities have their magic. But when I plan a trip away, even if it’s just for a weekend, I crave something completely different.

Enter: the Tuscan countryside.

Tuscany ticks every one of my boxes. Rolling green hills that look like they’ve been painted into existence. People who greet you like family, even if you don’t speak the same language. Food that makes you audibly sigh mid-bite. Wine that flows as freely as the conversation. And, most importantly, a kind of golden stillness that makes your nervous system unwind in the best way. This is a place where you slow down not because you’re told to – but because you can’t help it. 

If, like me, you’re craving a reset that doesn’t involve hordes of crowds or frantic sightseeing, here’s how to spend 72 hours soaking up the best of Tuscany: the slower rhythms, the richer flavours, and that rare kind of joy that lingers long after you leave.

Day 1

Check Into... Castello di Casole in the heart of Tuscany, specifically near the town of Casole d’Elsa in the province of Siena. It’s the jewel of the area: a restored 10th-century-castle-turned-boutique-hotel surrounded nded by a 3,200-acre private estate of hills, vineyards and olive groves. With panoramic views, a dreamy pool and interiors that mix rustic charm with quiet luxury, it’s the kind of place you book for a special occasion – a milestone birthday, anniversary or a long-overdue escape. The only downside (besides the price tag – rooms start at £1,200,, so this is high-end luxuryso this is high-end luxury) is that the estate is so beautiful, you might not want to leave. And you don’t have to stay the night – Castello di Casole is open to non-guests. Just make sure to plan accordingly: book ahead for a spa treatment, a pasta-making or eco-printing class, or simply enjoy aperitivo on the terrace.

Get Around By... Car. In Tuscany, freedom is everything – and that means having wheels. Make sure someone in your travel group brings their drivers licence, because exploring at your own pace is part of the magic. If you’re staying at Castello di Casole, electric bikes are perfect for nearby adventures, or the concierge can arrange a driver for longer trips.

Savour A Slow Lunch At... La Cantinetta, a family-run spot tucked into a 10th-century village in the Chianti hills between Florence and Siena. Order whatever’s in season – likely wild boar, fresh pappardelle or something smothered in truffles – and linger over a glass (or two) of local red.

Take A Stroll Through... The cobbled streets of Casole d’Elsa, a nearby hilltop town filled with charm, artisan studios and breathtaking views over the Val d’Elsa. While there, pop into the Civic Archaeological Museum,, which is full of Etruscan artefacts from 5^th to 3^rd Century BC, long before the Romans came to the area.

Embrace The Local Ritual Of... Aperitivo: the ultimate happy hour. Find a café in Casole d’Elsa’s main square, order a refreshing spritz and sip slowly while soaking up the relaxed local buzz – the perfect way to whet your appetite before dinner.

Reserve A Slice Of Heaven At... La Pergola di Radicondoli, nestled in the hilltop village of Radicondoli. You’ll find plenty of pizza in the region, but this spot might just serve the best. The creative menu features a variety of toppings and dough styles – Roman pala (shovel) dough included – for a truly authentic and unforgettable taste. 

Spend The Morning In...Volterra, a lesser-known gem also perched in the Tuscan hills between Florence and Siena, known for its Etruscan and Roman history. Wander the ancient walled streets to get your steps in, explore the atmospheric Roman theatre ruins and enjoy a quiet espresso in the sunlit piazza – is there a better way to start to the day?

Come Afternoon, Head To... San Gimignano, Tuscany’s “Medieval Manhattan”. Unlike Siena and Florence, which lost most of their towers due to wars, catastrophes or general urban renewal, San Gimignano has managed to conserve 14 of its UNESCO-protected ancient towers, creating an epic skyline that transports you straight back to the Middle Ages. 

Make A Gelato Stop At... Gelateria Dondoli, located in the heart of San Gimignano. It’s regularly voted the best gelato in the world (try the pine nut flavour) – pure artisanal perfection in every bite.

For Dinner With A View, Book Into... Ristorante Arnolfo in Colle di Val d’Elsa – a two-Michelin-starred spot that reinterprets Tuscan cuisine in extraordinary ways. Go for the tasting menu if you’re feeling indulgent, and ask for a terrace seat – the sunset here is spectacular.

Day 3

Ease Into The Day With... A slow breakfast on the terrace or a walk through Castello di Casole’s grounds – there, you’ll find 60 varieties of roses and beautiful olive groves. Then hit the road to soak up more of the Chianti region – you’ll pass postcard-perfect vineyards, cypress-lined roads and hilltop villages along the way that practically beg for a photo stop at every turn. 

Indulge In A Leisurely Lunch At... Osteria di Passignano, a must-visit for food and wine lovers. Nestled among Chianti Classico vineyards, this Michelin-starred spot serves up delivers refined Tuscan flavours in a stunning setting – and, perhaps most importantly, it’s home to what many call the best Tiramisu in the region. Bonus: you can request a wine cellar tour before or after your meal.

Take An Optional Detour... West, to the beach. Closer to Siena than Florence, Castiglione della Pescaia boasts golden sands, pine forests and relaxed beach clubs with plenty of fresh seafood. For a more exclusive escape, drive a little further to Monte Argentario, where dramatic cliffs and turquoise coves offer a quieter, Tuscan spin on la dolce vita. 

End Your Trip On A High... Back at Castello di Casole, whether you’re staying or not. Book a spa treatment (the reflexology is unbelievably magical) or a hands-on workshop in the gardens. Then head to the estate’s restaurant, Tosca, for one last dinner of dishes, such as succulent beef or classic vegetable ravioli, all made using locally sourced ingredients – and, of course, a final glass of local wine before you head home.