How to have the perfect weekend in Tuscany
If you thought that the photo above was an artwork, you’d be forgiven. Sights like this one are common in Tuscany, where the scenery seems lifted from a landscape painting and you frequently can’t quite believe your eyes.
The central region is bucolic Italy at its best, from the holiday homes and converted farmhouses of ‘Chiantishire’ (so-named for its popularity with Italophile Brits), to the hill-top medieval villages and hamlets, or rather, borgos, some of which now form the vast estates occupied by luxury hotels.
The pastoral parts of Tuscany are magical, but the capital Florence could tempt even the most hardened bumpkin away from the rolling hills, if only to see the most beautiful building in the world (in my humble opinion): the Duomo – officially the Cathedral of Santa Maria del Fiore, construction of which began in 1296 and wrapped up in 1436, with Filippo Brunelleschi’s dome the literal crowning glory. Other cultural highlights on show in the Tuscan capital are the Botticelli masterpieces housed in the Uffizi and Michaelangelo’s David, displayed in the Accademia Gallery.
Who hasn’t dreamt of packing it all up and channelling Diane Lane in Under the Tuscan Sun, or Elizabeth Gilbert (via Julia Roberts) in Eat, Pray, Love? For the rest of us, there are shorter trips to get a taste of the good life, if only temporarily. Here’s how to spend a dream weekend in Tuscany…
Stay at Castelfalfi
At many luxury resorts in Tuscany, historic borgos have been repurposed and converted into hotels, with rooms, suites and restaurants spread across the various outbuildings. One such stay is Castelfalfi, set on a vast estate spanning a golf course, a village and endless acreage. Guests can choose between slick contemporary rooms (quite the rarity in Tuscany) in the main building and more traditional options in the old tobacco warehouse.
The grounds are also dotted with vineyards, olive groves and various self-contained villas, some with private pools, including Villa Bianchi, which is the kind of holiday home that will have you bidding for the deeds when you have to leave.
Alongside terracotta floors, archways and vaulted brick ceilings sit more modern additions, such as a Marshall jukebox with a selection of vinyl records, chenille dining chairs and a chandelier that looks like it’s made out of illuminated candy canes. The kitchen also houses a gorgeous selection of ceramic-fruit-adorned serving platters, jugs and fruit bowls.
A short stroll away from the main building and the tobacco warehouse is the heart of the village, with hazy views in every direction, a castle and a small high street that would put a more humble hamlet to shame with the chi-chi wares for sale in its smart boutiques, which include the only outpost outside of Milan and Portofino of Whyci Milano.
Go truffle-hunting
If you want to see how the region’s most elusive funghi are searched for, or if you just love dogs, spend an afternoon truffle-hunting with Savini Tartufi. The family have been seeking out the prize tuber since 1920, selling their unearthed trophies for as much as €3,000 a kilo. For me, someone who thinks truffle smells (and tastes) of bleach (I know, sacrilege), hanging out with the dogs, Fiuto and Bruno, was the highlight.
Bruno would alert his master to a find in the regular way, by barking, but Fiuto had an idiosyncratic approach: he would press his entire body down onto the ground to guard the earth around his treasure. Unlike pigs, who were once used in the quest but had to be replaced because they kept scoffing the truffles, the dogs are loyal, waiting patiently for their master to take the bounty off them and administer their treats. As we drove home and darkness fell, a huge hare and a deer scampered across the countryside, forming another painting.
Tour the medieval village
Learn about the history of the medieval village of Castelfalfi on a tour of the borgo, where a guide will take you past the tabaccaia, as you hear about the women who used to roll cigars here, to the 13th-century church, with its bell tower and frescoes of local families painted centuries ago; via the boutiques – a Stefano Ricci store, a wine shop, even a bank with an incongruous-looking ATM – to La Roqqa, the castle at the end which looks out across the surrounding countryside.
Our guide, Jacapo, said this vantage point made him feel like Simba and Mufasa, when father tells son, ‘Everything the light touches is ours’. Sadly, we weren’t the proprietors in this case but we could appreciate the sentiment. In the past, weddings here have had tables set up all the way down the main street of the village – party perfection.
Eat your way around the Castelfalfi confines
As befits a resort of its size, there are lots of restaurants and bars at Castelfalfi to work through, starting with Olivina in the main house, where we dined on veal Milanese that was aptly named ‘elephant’s ear’ to give an indication of its size, lobster tortelli, and wagyu beef with caviar and celeriac.
Whole tasting menus dedicated to black or white truffle can, naturally, also be served. There’s also Il Rosmarino, which celebrates the food of Tuscany, and a clubhouse close to the golf course for carb-heavy lunches and charcuterie and cheese boards. For something unforgettable, the estate’s chef Davide De Simone sets up shop inside the medieval castle walls for an especially romantic dinner service from Wednesday to Sunday.
On the off chance that you wake hungry, the beautifully curated breakfast buffet, with a restrained edit of pistachio cream, smoked salmon, charcuterie, loaves of bread to slice and assorted pastries, awaits, and there’s a terrace so you can soak up the scenery as you eat alfresco.
Visit neighbouring hilltop medieval villages
From Castelfalfi on a clear day, you’ll be able to see the sea. Also visible from La Roqqa at the furthest reaches of the borgo are some equally attractive neighbouring hill-top hamlets. One of the prettiest is San Gimignano, a half-hour drive south, ringed by 13th-century walls, with a fresco-graced 12th-century church and a triangle-shaped piazza lined with ancient houses. Volterra is just as captivating, with more historic city walls, bell towers and medieval frescoes to admire, alongside the ruins of the Etruscan Acropolis.
Relax at Castelfalfi’s RAKxa spa
Nowhere does spa as well as Asia, where the treatment beds are wide enough for the diminutive but freakishly strong therapists to straddle and contort you, providing peerless tension release. And imported all the way from Thailand is the RAKxa spa at Castelfalfi, where you can book everything from a quick massage or facial, to a full-blown overhaul programme.
The indoor-outdoor pool, with its view out across the Tuscan landscape, is a tonic in itself, but for something a little more focused, sign up for detoxification therapy, cupping, energy medicine with crystals, reiki, chakra balancing or gait analysis. The spa holds seasonal retreats, lasting three nights or longer, that aim to help guests regain their fitness, with hiking, wholesome food and Tuscan truffles on the agenda.
Play a round of golf
Golf has a bit of an unsexy reputation, but for the converted, there are fewer things they’re more passionate about. If you fall under that category, Castelfalfi is home to one of the finest courses in Italy, with an annual membership fee of €2,400 for the privilege of teeing off on these fairways. There’s a clothing and accessories boutique on-site, so you can get yourself suitably kitted out.
More Italian holiday ideas:
- The most stylish stays in Rome
- Lake Como's most scenic Airbnbs
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