Few overseas adventures sound as glamorous as spending summer 2025 in Tuscany. However, don’t be fooled into believing that all of this idyllic region’s best bits start and end in Florence.
While the capital’s world-class art galleries and monuments are undeniably wondrous, I believe Tuscany’s real charm and beauty can be found away from the city’s crowds, in particular, amidst its picturesque, rolling hills.
Offering postcard-perfect scenes of medieval hilltop towns, ancient castles, lush olive groves and cypress trees, journeying through the Tuscan countryside is an enriching experience you’ll never forget.
Here are six of its many highlights…
The setting for Daniel Craig’s iconic rooftop chase in 2008’s Quantum of Solace, the enchanting walled city of Siena, is every bit as beautiful as it looks on screen. Small and walkable, it’s far less busy and crowded than Florence, but filled with just as many cultural wonders.
Start your visit in the UNESCO World Heritage–listed Piazza del Campo, the venue of the world-famous Palio di Siena horse race. While attending the race itself is not for the faint-hearted (picture many cramped hours waiting in the summer’s heat), the piazza itself is a lovely place for people-watching, relaxing, and – of course – treating yourself to an icy cold, sweet gelato on a warm summer afternoon.
The Gothic Siena Cathedral is simply awe-inspiring, while the Museo dell’Opera del Duomo, one of Italy’s oldest private museums, is home to an extraordinary collection of sculptures, exquisite textiles, manuscripts, and many more amazing artworks.
Once you’re done with the piazza, simply enjoy getting lost amongst the city’s narrow cobbled streets, where endless boutiques, cosy restaurants, and bustling cafés are just waiting to be explored.
There is great debate over which is the prettiest hilltop town in Tuscany. But the truth is, they all have their own unique fairytale charm.
Scattered across the undulating landscape, you can easily spend a pleasant day or two hopping from one quaint settlement to the other, exploring the hidden treasures of their centuries-old winding lanes.
From San Gimignano’s dramatic 14 towers to the 3,000-year-old Volterra (the oldest city in Italy) and the striking fortifications of Monteriggioni, each town is brimming with history, art, and interesting stories. And, if you’re a Twilight fan, you might recognise Montepulciano from its role in New Moon.
Equally suited to active types as it is to cultural enthusiasts, Tuscany is a great place for hiking and cycling.
One of the most popular routes is the Via Francigena pilgrimage path. Used since the Middle Ages and running from the north to the south of the region, meandering along this important thoroughfare is the very definition of slow, sustainable travel.
If you grab this chance to take your time and appreciate Tuscany’s glorious woodlands, tiny villages, castles, and valleys from a different perspective, you’ll see and experience far more than you ever would by car.
Once you try pici (or pinci, as it is known in some parts) you’ll want to order at least one bowl a day.
Originating from the province of Siena, this hand-rolled pasta is like a chunkier version of spaghetti, and you’ll find it served at every quaint restaurant in Tuscany.
It is served with sweet and juicy tomato sauce, rich meat ragù, and more sumptuous toppings. Also, the renowned Monteverdi Culinary Academy and many other cooking schools offer pici-making classes.
Visit Monteverdituscany.com
The white truffles of Tuscany are some of the most elusive and luxurious in the world. Providing the ideal excuse for a late summer or early autumn escape, truffle-hunting season runs from September onwards, and it’s an absolute must-try for any self-confessed truffle addict.
Inviting you to join real truffle hunters and their dogs as they search for these underground treasures in Tuscany’s tranquil forests, the truffle-hunting excursions organised by the family-run Savini Tartufi are renowned across the globe, and they even end with an exclusive truffle tasting menu.
Visit savinitartufi.it
Tuscany is brimming with stunning hotels, but nothing else comes close to the authentic elegance of Rosewood Castiglion del Bosco.
Built on an immaculately restored 900-year-old estate, it looks and feels just like a traditional Tuscan village.
Replete with intricately designed rooms and villas, multiple infinity pools, a spa, a cooking school, and Italy’s only private golf club (for guests and members exclusively), the estate is surrounded by pretty hiking trails, and dotted with friendly wild deer.
Visit rosewoodhotels.com
