Road trips can bring a wealth of experiences, from once-in-a-lifetime moments to remote mechanical failures. Driving around Italy – specifically, Tuscany and Umbria (and the surrounding areas) – promises picture-perfect rolling vineyards, village markets, stunning natural springs and visits to hidden trattorias that might stay open past the customary 3pm lunch service to let you taste their house pasta. Though, pockets of such winding routes can be a nerve-fraying exercise in braking and accelerating, and then there’s the looming threat of biblical rain, ready to test your anti-aquaplane steering ability at any given time. But what’s a road trip without a few physical and psychological bumps along the way?
Given the expanse of the area, there are seemingly endless routes to take. Depending on your desired start point, it’s possible to fly into Perugia, Rome or Florence. The former is a small airport with limited departures, but it places you in the middle-upper calf of the country’s boot. With a vast selection of international flights, Rome is a solid choice if you’re keen to explore Umbria and southern Tuscany – and if you fancy a stopover. My boyfriend and I wanted to wander the Florentine streets, so opted for the latter.
We flew direct from London City, collecting our car after one night from a charming, fresco-covered Airbnb that was equidistant from the Santa Maria del Fiore and Basilica di Santa Croce. And a week later, we dropped off our rental to enjoy a final night at Hotel Helvetia & Bristol, accompanied by aperitifs at The Place Firenze and the aforementioned biblical rain (luckily, sans car at this point).
With several hours of driving ahead and temperatures in the high 30s, a restful night in Florence was much appreciated. I’d recommend arriving on a weekend, as we did, to witness the city buzz before venturing into the Italian wilderness. We didn’t want to feel too locked into a schedule, so timings were flexible throughout our stay, and we aimed for no more than three hours of driving per day, which allowed us to fully immerse ourselves in the journey, savour the surroundings and culinary delights (when we were within Italian lunchtime hours), and stop anywhere we wished. We (meaning my boyfriend) toyed with hiring a classic car, which would have been romantic but come with the ever-present fear of breaking down in an area with no phone signal. Plus, there was the added stress of scratching the paintwork when navigating narrow hillside villages. Our chosen convertible was ideal, offering maximum horsepower and 360-degree views.
Looking at the map, our route was a tangle of (intentional) zig zags that dipped in and out of Tuscany and Umbria, via Chianti, Arezzo, Montepulciano, Maremma and the fringe of Perugia, with stop-offs at several unique and beautiful hotels, including La Darbia, Vocabolo Moscatelli, Castello di Vicarello and Borgo dei Conti (more on those below). We’d have loved to stop by Siena or the coast, as so many road-trippers do, but we decided to save for next time.
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Balancing recommendations and straying off the beaten track, we scouted out places suggested by friends, but remained open to establishments that we’d stumble across. Swimming spots were common, though I warn some were tricky to find – be prepared to embrace a steep forest floor in flip-flops, or bring a more substantial pair of shoes. Top tip: Italian supermarkets really level up the packed-lunch experience, and in turn ease the discomfort of leaves stuck between your toes.
I’d recommend our route in any order – though, research ZTL zones and tolls before you set off to avoid getting caught out. I’d also highly recommend the places we stayed, all of which brought incredible hospitality and, by no surprise, top-tier food. While each place differed in their approaches, there was a clear sense of regional pride: kitchens championed local ingredients, and the teams were more than happy to offer local insights.
Should you feel inspired, below, the best hotels in Tuscany and Umbria are now taking bookings for 2027 – some are even available for last minute stays this year.
Jump to:
- Where to stay in Umbertide: Vocabolo Moscatelli
- Where to stay in Tuscany: La Darbia
- Where to stay in Perugia: Borgo dei Conti
- Where to stay in Maremma: Castello di Vicarello
- Where to stay in Florence: Hotel Helvetia & Bristol
For a luxury home away from home: Vocabolo Moscatelli, Calzolaro
Founders Cathi and Fred have built a special place in Vocabolo Moscatelli. The team has cultivated a warm, welcoming atmosphere that encourages a sense of community among guests. Building on its history as 12th-century monastery, the layout encourages mingling: the rooms upstairs are led down into an intimate, unpretentious bar that feels like a kitchen island, decorated with a medley of local tiles that we wanted to take home with us.
These were but a snapshot of the thoughtful interior details – think flea markets finds and bespoke artisanal pieces – that sets Vocabolo apart from a “regular” hotel. This attention to detail extends to a range of activities and itineraries handpicked by Cathi and Fred for guests to enjoy. Those keen to venture beyond the delightful confines of the pool and pristine gardens can tap into the couple’s expansive knowledge of the area, and embark upon a bike ride, truffle hunting or a city tour. We visited the Atelier Giuditta Brozzetti, a sanctuary of textiles that preserves millennia-old hand-weaving techniques, housed in the oldest Franciscan church in Perugia (a must-see).
Staying in at Vocabolo can be as relaxing or active as you like – massages in the chapel, pottery sessions and yoga are Vocabolo signatures. We unwound with a watercolour class, house-special smoky Negronis in hand, surrounded by the abundant lavender that covers the main building, and were also given a pasta class by Nicolo. Thanks to his guidance, our pasta turned out surprisingly well, but the real foodie treat came when we sampled his dinner menu, which featured light twists on well-loved classics and nostalgic dishes inspired by his childhood, starring produce from the garden and independent local suppliers.
However a guest chooses to approach Vocabolo Moscatelli, they’ll come away completely restored. And in our case, not wanting to leave.
For a boutique stay in the Tuscan hills: La Darbia, Chianti
A 45-minute drive south of Florence brings you to the remote, wine-renowned Chianti region, where earlier this year La Darbia opened its latest hotel offering. Positioned on a hillside in between Panzano and Greve, the 15-hectare property spans farmhouse clusters – which were formerly an 11th-century hamlet – encircled by lavender fields, luscious olive trees and wildflower meadows that are home to 40 beehives, from which the team produces homemade olive oil and honey, respectively. Whether enjoyed from the bedrooms, the two pools or the courtyard dining area, the views are spectacular and accompanied by the therapeutic hum of wildlife.
And while there’s plenty to see as far as nature is concerned, the interiors also make for a calming retreat: natural materials, including pietra serena, terracotta, travertine, and wood, bring pared-back tones that work in harmony with the landscape. The historic walls and ceilings have been carefully restored to not interrupt their original form, with contemporary details woven throughout the 17 suites, which vary in size and guest capacity, but united in their relaxing feel.
La Darbia truly offers respite from the outside world – which was perfect for us Londoners. Everything is taken care of: most notably, the food. Adhering to an exclusively Tuscan menu, guests are treated to a culinary journey from breakfast to dinner, which – for reasons mentioned previously – is best enjoyed al fresco.
For a peaceful getaway with serious views: Castello di Vicarello, Maremma
It would take a long stay at Castello di Vicarello to make an inventory of the all objets held within its four walls. With endless statues, relics, textiles and literature, the hotel is a reflection of its owners’ – a family that spent nearly two decades restoring the 12th-century castle before opening its doors as a boutique hotel – eclectic taste. No space is the same: sumptuous deep-wine and leather furnishings are set against the historic backdrop of restored wood, stone tiles and brick, with injections of marble and copper in the bathrooms. Large-scale artworks and paintings line the walls, while the floors are covered with elaborate patterned rugs and, true to its ancient roots, candles are dotted throughout.
The castle sits at the end of a serpentine Tuscan road, meaning there are plenty of photo opportunities. But the real winning shots can be captured in its surrounding gardens. One of two marbled pools is perched on the hillside with panoramic views, and the other is a short walk away in the olive grove. Don’t expect a battle for sun beds: these are shared by only 10 suites, allowing for a tranquil atmosphere throughout. (The separate Villa La Vedetta has its own pool, while the Spa Suite has a hot tub.)
Further views can be seen from the balcony, where breakfast is served, or the terrace, where aperitifs and dinner commence every evening. The menu is centred around a farm-to-table concept, with food that celebrates a range of Tuscan culinary touch-points: the meat is sourced from local butchers – longtime collaborators of the family – cheese and salumi are from nearby villages and the fish is from a market located just under an hour away in Grosseto. There’s plenty to see – and consume – at Castello di Vicarello. Staying in a Tuscan castle, for one, is a unique experience.
For a taste of Umbrian history: Borgo dei Conti, Perugia
Guests will witness one of the key features of Borgo dei Conti a kilometre away from the reception. The driveway meanders through the 16-hectare estate featuring many, many trees, each of which – according to a Bioenergetic Landscape study – possess energy and health benefits. The vegetation makes for impressive entrance, and guests are encouraged to fully immerse themselves in nature during their stay, be it a short walk, brief pause or yoga session alongside the flora and fauna. Because relaxation is at the heart of Borgo dei Conti: from the all-encompassing spa treatments to the comfortable suites and infinity pool, the priority is to switch off. (Unless, of course, you fancy playing padel, tennis or billiards.)
Every aspect of Borgo dei Conti has a presence – above all, the architecture, with some parts dating back to the 13th century. There’s also the 19th century-hailing, neo-Gothic Limonaia, where one of the restaurants can be found, and various buildings that have undergone renovation in the years prior to its current state as a hotel. The property’s interiors have been sensitively modernised throughout in a way that complements the heritage, with curvaceous wooden furniture, gilded mirrors and ceilings accented by dark metal light fittings.
The same sensibility runs through the communal areas and the restaurants – the refined Cedri, housed in the aforementioned Limonaia orangery, and the more casual L’Osteria del Borgo, both of which offer seasonal menus curated around local produce. Speaking from experience, the chef’s tasting menu – and wine pairings – showcases a full spectrum that you won’t regret. So, too, the cocktail bar which, with its mediaeval charm and broad libation offering, beats a city spot any day.
For Florentine city break: Hotel Helvetia & Bristol, Florence
The Hotel Helvetia & Bristol is like a labyrinth. In its underbelly, there lies a spa, complete with Roman baths. A floor up, there’s a grand Florentine-style entrance and reception and a restaurant to the west side of the building, housed inside a former bank. In the levels above, there’s a maze of rooms and suites, unique for their vaulted ceilings, elaborate chandeliers and tall windows looking onto the streets below.
Location has made the early-19th-century Hotel Helvetia & Bristol a firm favourite among international visitors. Nestled on a side road near Palazzo Strozzi and Duomo, amidst a string of luxury stores, it serves as an ideal outpost for anyone after convenience, whatever the length of stay. Within walking distance of tourist spots and eateries, it’s placed in the beating heart of Florence.
Totalling 89 rooms, 64 of which are in the Helvetia Wing and the rest in the Bristol Wing, the rooms and suites reflect Florentine history and tradition. The latter, which was added in 2021, is the most modern aspect of the hotel. The final outcome reflects the original details through a modern lens: opaline glass, herringbone-oak flooring and cast-iron canopy beds, crafted by local artisans, all feature. But the restored furniture, antique paintings and Italian marble are the real talking points.