THINGS TO DO AND SEE AROUND CORTONA
Cortona is one of the loveliest hilltop towns in Tuscany. Famous for Frances Mayes book ‘Under the Tuscan Sun’ which has brought many culture vultures from all over the world to this cobble-stoned walled town with is tiny strade, many unpassable by cars, even a Fiat 500. There are places which give themselves away at once, and others which keep something back. Cortona belongs firmly to the second camp. It isn’t dramatic in the obvious way. It doesn’t fling itself at you with grandeur or noise or a parade of sights clamouring for attention. Instead, it unravels itself slowly, almost shyly, through details so small you could miss them if you were in the wrong frame of mind. The slant of late afternoon light on worn stone. The murmur of voices rising from a square just out of sight. A shutter pushed open somewhere above you. The smell of Italian coffee drifting from a bar you hadn’t noticed a moment before (and there are quite a few to choose from!)
This is one of the loveliest things about staying at La Casa Cappellina. You’re close enough to Cortona to make it part of the day, for a morning coffee, lunch or evening passegiata, but not so close that you feel pinned to it. The villa is close enough to sit in that sweet spot between immersion and escape. You can wander into town (a 40-minute walk through woodland and road) when you feel like some exercise, then head back home again to stillness, to birdsong, to the pool, to a terrace, glass in hand as the sun sets and the colours over the hills soften into evening. You’re not locked into a schedule of sights or sightseeing, and we highly recommend, on your first visit, simply wandering around the town, soaking up the atmosphere and looking up! After a few days, Cortona becomes less of a destination and more of an old friend.
It’s best approached without too much determination. We know that goes against every instinct to plan, optimise, and make the most of things, but Cortona doesn’t reward haste. It asks you to take your time and to live slowly and to live life like a local. To let one street lead to another. To pause in small, cool churches where candles flicker against stone. To peer into shop windows, not because you need anything (though you will be tempted!), but because the objects themselves, handmade bags and jewellery, wines, art, olive oil, are beautiful enough to make you stop. To sit in the Piazza della Repubblica over a coffee and notice who is greeting whom, who is rushing, who is not. There’s always a little life and story unfolding if you’re prepared to sit still long enough to see it.
One of the pleasures of being here is that the town changes character by the hour and by the season. In the morning, particularly if you go early, there is a softness to it which feels intimate and personal. An early morning walk from La Casa Cappellina to Cortona is a treat; you feel as if the streets are yours with no one else around. It almost feels like a stage. The streets are quieter, deliveries are being made, doors are being opened, and there is the distinct sense that you are seeing the place before it has fully dressed for the day. By late afternoon and into the evening, the mood shifts. People emerge and the Passeggiata (walk around) begins. Families stroll without purpose other than to be out together in the evening air. It’s one of the great Italian rituals, for the entire family and one of the easiest to fall into. You tell yourself you’re only going for a short walk, and before long, you’re part of it, moving with everyone else in that unhurried, end-of-day rhythm.
Of course, Cortona is only the beginning. One of the quiet luxuries of staying at La Casa Cappellina is how easy it is to dip in and out of the surrounding landscape and Tuscan countryside, which is as much a part of the experience as the town itself. The roads around here are reason enough to get in the car, even without a destination in mind. They wind through olive groves and cypress-lined ridges, past vineyards, stone farmhouses, pockets of woodland, fields of sunflowers and views which keep expanding, some dotted with families of wild boar. You can spend an afternoon taking the smaller roads and be rewarded again and again by the simple pleasure of looking.
The nearby Tuscan town of Arezzo (about a 45-minute drive) makes an excellent day out, especially on the first weekend of the month when the antiques market spills through the streets and piazzas. Even if you have no intention of buying so much as an old postcard, it’s impossible not to be drawn in by the jumble of linen, silverware, paintings, furniture and curious little bits of Italian domestic history whose former lives you can only guess at. Pienza, too, is worth the drive, not only for its famously beautiful position above the Val d’Orcia but for the pleasure of lunching at La Bandita Townhouse and stretching the day longer than you intended. Then there’s Lake Trasimeno, which has a languid charm all its own, especially in warmer weather when lunch by the water can slide quite naturally into an entire afternoon.
Arezzo, Tuscany
Yet what we like most about being based here in the Tuscany countryside is that none of these outings feels mandatory. There’s no pressure to turn every day into a trip to do or see something. Some of the best days here in Tuscany are the ones with no plan at all. A slow breakfast on the terrace. A swim before the sun reaches its full strength and again at sunset. A walk into town. A stop for a drink. A detour down a side street because the light looked beautiful there. A bag of shopping carried home for supper. The rosemary and lavender in the garden brush with your hand as you pass. The church bells mark the hour and are the only reminder of time passing.
That is the real charm and seduction of this corner of Tuscany. It simply goes on being itself. Cortona doesn’t ask to be conquered, completed, ticked off a list or consumed. It asks only that you stay long enough, and you begin to understand that the pleasure here lies not in racing from one sight to the next, but in letting the days open naturally, each one gathering its own small, memorable moments.
By the time you leave, you’ll already be longing to come back.