The birthplace of the Roman Empire, Renaissance and gastronomic excellence, Italy is more densely layered than a lasagna. There’s a lot of ground to cover, so we’ve mapped out routes and picked the most charismatic hotels, from the villa-edged lakes in the north down to the glamorous isles off the toe of the boot, for the best road trips in Italy. There are romantic sprees through classic honeymoon spots, family-friendly breaks in the country and scenic stretches to cover.
ROUTE ONE: ADVENTURES IN AMORE
TWO NIGHTS IN TUSCANY
To describe this part of Italy is to veer into poetry: the golden sunflower fields laced into a patchwork with olive groves and vineyards, winding roads edged with graceful cypress trees, villages that time has left well alone… And so it’s become the watchword for Italian amore and makes an excellent starting point for a romantic road trip for couples. Hop in your – hopefully sporty – car and wind up the scenic drive to hilltop hotel Castello di Vicarello. Maremma’s countryside is quite the seductress and the hotel is the feather on Cupid’s arrow – the perfect start to your Tuscany road trip. It’ll woo you with wine tastings from the owners’ slopeside vineyards, lessons in how to perfect your papa al pomodoro and tiramisu with cookbook writer and chef Aurora Baccheschi Berti, chances to pitch in with the olive and grape harvests and even leather-tooling workshops to make stylish love tokens for one another. And, this 900-year-old has aged very gracefully, with its wood-beamed rooms that’ll slot neatly into your Tuscan reveries.
TWO NIGHTS ON THE AMALFI COAST
However, Tuscany has a love rival, a six-hour drive away. In the south, the Amalfi Coast looms even larger in the romantic imagination. Quite literally, as its cliffs cleave majestically out of the Tyrrhenian Sea, and the roads hewn into them sweep through oft-Instagrammed villages that cascade over the rockface – and, those sparkling views compete for Italy’s most head-turning. Yes, driving the Amalfi Coast is a magical experience. It’s worth taking the longer Amalfi Coast drive to the next hotel on your list – Palazzo Avino – straight shooting down the coast then cruising round the Sorrentine Peninsula, in order to pause in Positano and Praiano for photoshoots, zingingly fresh fish dinners and shots of locally made limoncello (not too many for the road, mind). Palazzo Avino was a private, pink-hued 12th-century villa now made generously available to honeymooners and the like. It’s effortlessly Italian in style within and there are terraced gardens, an on-high pool and a private beach club nearby, with sunlounger-topped platforms from which you can lovingly gaze out over the water.
ONE NIGHT IN CAPRI
Drive back into Sorrento and swap your car for the ferry – Capri’s slender streets are best navigated on foot. The crossing just takes 30 minutes before you can skip onto the glamourpuss isle that won the hearts of Jackie Kennedy, Audrey Hepburn, Grace Kelly and other luminaries. Check in at JK Place Capri, a stay that’s nailed the locale’s dress code and sits pretty amid soaring shoreside cliffs. With this as your base, you can head into central Capri for high-fashion sprees (don’t forget a pair of iconic Canfora sandals), rent Vespas and zip along coastal roads and nose around well-preserved Roman-era villas. And get a view from the top on the Mount Solaro chairlift before a sumptuous meal of Capresi delicacies.
ROUTE TWO: A PASSAGE THROUGH PUGLIA
TWO NIGHTS IN MONOPOLI
A different idea for an Italian road trip is sweeping across the south. And, with a private beach and no less than seven pools, getaways go swimmingly at Puglian hideaway La Peschiera. But make sure your swimwear is also suitable for posing, because the hotel can hire you a private yacht for Adriatic adventuring or arrange a deep-sea fishing session, followed by a cookery class to turn your catches into tasty Apulian dishes. When you’ve dried off, cycle along the Appian Way past conical trulli huts to the sprawling Roman ruins of Egnazia. Or get to know your Negroamaros from your Fianos on a wine-tasting trip. If you don’t fancy another dip, get high on a panoramic helicopter tour to see the Valle d’Itria and its charming historic towns laid out before you.
TWO NIGHTS IN CISTERNINO
By now you’ll be familiar with the sight of the pointy-roofed trulli Puglia is famous for and deep in Cisternino’s countryside you’ll have the chance to stay in one. Borgo Canonica is a fully restored village turned hotel where these unique structures have been luxuriously upgraded with rustic trappings and bouncy beds. A large pool and a chef who can work wonders with the local orecchiette are welcome updates too. While away your days swimming and snacking, with the odd wine tasting or cookery class to mix things up a bit. The Borgo is orbited by some of the country’s most comely villages and towns – take a more meandering road trip into Cisternino to try succulent bombetta, Trani for some castle admiring and fresh fish, and brilliantly white Ostuni for some photo ops.
TWO NIGHTS IN LECCE
Next up is one of Lecce’s loveliest stops. Just above the tip of Italy’s heel is Gagliano del Capo, a commune that has artfully bleached buildings, luminous grottoes to swim through and arrestingly beautiful beaches where the Ionian’s dazzling turquoise waters lap sands sheltered by cliffs. And, along the café- and tree-lined Corso di Umberto, lies Palazzo Daniele, a 19th-century villa turned into a haven for aesthetes by owner and art aficionado Francesco Petrucci and owner of Smith stablemate G Rough. Frescoed walls and ceilings and intricate mosaic flooring are met with modernist furnishings and idiosyncratic artwork. As the last stop on this Italian road trip, it’s a place where quiet contemplation and restorative afternoons amid the garden’s orange groves are encouraged – until dinnertime, that is.
ROUTE THREE: LINGERING BY THE LAKES
TWO NIGHTS BY LAKE COMO
When it comes to inspiring vistas, Lake Como is something of an overachiever – after all, who can say they’ve captivated Virgil, Leonardo da Vinci, the Romantic poets, Bellini, Puccini… And, well, George Clooney. It’s a must-see stop on any road trip in Italy’s north, with handsome villas that crowd along the lake’s banks like lovesick admirers. Grand Hotel Tremezzo is possibly the grandest to grace them, and almost certainly the most flamboyant. Its pool is sunken into the lake and appears to float; its interiors are gilded, colonnaded and crafted from rich local materials; and, if you’d like a little privacy, the separate exclusive-use Villa Sola Cabiati has some of Napoleon’s old belongings in the attic. Activities are largely lake-based: swoop across the water in a vintage speedboat, hop in a seaplane for a bird’s-eye view, and you can cycle along the edges – the hotel will prep a decadent picnic for you.
TWO NIGHTS BY LAKE GARDA
The equally eye-catching Lake Garda, with its cellophane-clear waters and mountainous surrounds, is around a two-and-a-half-hour drive to the west. Along the way, thread your road trip through Lake Lugano and Lake di Varese to make it extra scenic. Garda, the largest of Italy’s lakes has been accentuating the landscape since the Dark Ages and has had its fair share of literary admirers too. Put yourself in prime position along the Lombardy coast for views at Lido Palace hotel, an Art Nouveau villa given a dynamic modern makeover by architect Alberto Cecchetto. Activities require a little more adrenaline here, whether you’re windsurfing across the lake, paragliding over it, scaling mountain or peddling a bike around one. But, after your exertions, the svelte piano bar and haute dining offer lavish ways to unwind.
ROUTE FOUR: A ROAD TRIP WITH LA FAMIGLIA
THREE NIGHTS IN CASTIGLIONE DELLA PESCAIA, TUSCANY
For kids, Tuscany’s greener bits are one ongoing playground – and all you need for an enviable Italian road trip. Bambini are warmly welcomed in restaurants and bars, village-hopping makes for fun IRL history lessons and hotels have plentiful distractions. One such is L’Andana, once a villa for the Medici’s Grand Duke Leopold II, now a come-one-come-all rustic hideaway. The rolling grounds and large pool (unsupervised, so parents, keep an eye out) do some of the heavy lifting when it comes to entertainment, and the rest is looked after by neighbouring sister property Casa Badiola, who have a sweet kids’ club with a shallow pool, ping-pong table, pinball machine and outdoor games and gardening. And for bigger kids, there are cookery lessons, tennis courts and mountain bikes to hire, plus an elegant apéritif spot.
TWO NIGHTS IN CAPALBIO, TUSCANY
A gentle 90-minute drive south down the coast is Capalbio in Maremma’s countryside. This medieval town has been fully restored to its crenellated and turreted glory, and there are plenty of notable buildings, including Collacchioni Palace, where Puccini played. Your children may be less fascinated by the tinklings of an operatic Italian composer, but they will be enamoured with Locanda Rossa, an eco-friendly, russet-hued farmhouse turned hotel where families can come together and relax. Smalls can knockabout in the playground or on the football pitch, splash in the pool for under-14s or make friends with the resident animals. The coast is just a 30-minute drive away for paddling in the surf and staff can arrange visits to local beauty spots, say, Lake Burano or Etruscan town Vulci. Rooms are modern and a good size for all the relatives, and the osteria can modify meals as wished.
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This article was updated for accuracy in September 2021