If there’s one thing Italy isn’t, it’s somewhere to tick off your sightseeing list. The country packs an incredible amount into a relatively small corner of Europe; one minute you could be cruising across an Alpine lake and the next, following the scent of truffles through Piedmont’s vineyards or standing beneath one of the world’s most exquisite art pieces in Florence. There’s no point in trying to do it all (that would take years!), but the real challenge is choosing where to begin. Here’s what we would do…
1. Stand inside the Colosseum in Rome
Rome doesn’t do subtle, and nowhere proves it quite like the Colosseum. Smack bang in the centre of the ancient city, this vast amphitheatre is the symbol of Rome and even more incredible in the flesh – all towering arches, sky-high stone tiers, underground chambers and that enormous arena floor. To think that crowds of 50,000-plus once gathered here for gladiator fights and exotic animal hunts is both thrilling and slightly chilling, and a reminder of how spectacularly dramatic the Romans once were.
Top tip: Book an early entry slot (less crowds) and include special access to the underground section, where the gladiators and animals were held – it’s by far the most fascinating part of the Colosseum.
2. Go truffle hunting in Piedmont
If you follow your appetite through Italy, it will eventually lead you to Piedmont. Come autumn, the Langhe hills fill with truffle hunters and their expertly trained dogs sniffing out the region’s prized white gems. Join a local trifolao for an early morning hunt and you might catch one being unearthed from soil, before making its way onto a plate of tajarin pasta come dinner. Add a glass of Barolo, a hazelnut gianduja dessert and perhaps a plate of agnolotti, and you’ll be in food nirvana.
Top tip: Truffle season runs from October to November, when Alba hosts its famous truffle fair and the region’s restaurants are at their most indulgent.
3. Take a gondola along the canals of Venice
It might not be under the radar, but nothing feels quite as Venetian as drifting along the city’s canals in a gondola. The sleek black boats have been navigating the waterways for centuries, steered by gondoliers who will take you past faded palaces and under the low stone bridges. Float into the quieter side canals, where washing sways above the water and neighbours chatter through their shuttered windows for a peek into everyday life.
Top tip: Gondola rides are cheaper and far quieter away from St Mark’s. Try boarding near the Rialto or in Dorsoduro for a more atmospheric experience.
4. Drive the Amalfi Coast
If ever there were a place to hire a vintage Alfa Romeo and drive with the windows down, it’s the Amalfi Coast. Twisting dramatically alongside tumbling lemon groves and the sparkling sea, the road from Sorrento to Salerno is one of the most beautiful in the world. Pull over in Positano for a cocktail at Franco’s Bar, then continue along the coast for a seafood lunch at Lo Scoglio in nearby Nerano. Later, cool off with a swim at Fiordo di Furore and a scoop of lemon gelato before the sun sets.
Top tip: If driving yourself feels daunting, hire a driver for the day. They know exactly where to stop for the best photos and where to find the prettiest swimming spots.
5. Stay in Masseria in Puglia
Scattered among Puglia’s ancient olive groves and sun-bleached fields are masserie (or fortified farmhouses), many of which have been transformed into stylish countryside retreats. Here, it’s all about breakfast beneath pergolas, dips in shady pools and long lunches of burrata, grilled organic vegetables and seafood. When you’re not horizontal by the pool, explore the whitewashed towns of Ostuni and Locorotondo, wander the trulli of Alberobello or detour to Matera where entire neighbourhoods are carved into rock.
Top tip: Some of the best masserie are hidden in the depths of the countryside so hiring a car is definitely the best way to get around.
6. Hike between the villages in Cinque Terre
Cinque Terre might look like it’s fallen straight off the front of a postcard, but the real magic happens on the winding paths between the villages. Old mule tracks, they criss-cross terraces of vines, clinging vertiginously to the cliffs with nothing but the bright Ligurian Sea below. Today, the tracks link the five villages of Monterosso, Vernazza, Corniglia, Manarola and Riomaggiore, rewarding those who wander with sea views and the occasional harbourside trattoria for a well-earned plate of pasta.
Top tip: The famous Sentiero Azzurro is the classic route, but the tiny vineyard paths above the villages are often even more beautiful and much quieter.
7. Road-trip through Italy
Follow the roads south of Florence, and Tuscany appears before your eyes in a picture-perfect banquet of vineyards and olive groves, idyllic, cypress-lined lanes and honey-coloured hill towns. There are highlights to hit – Montepulciano, Pienza and Montalcino spring to mind – but the trick is to stop when something catches your eye: a tiny enoteca serving Brunello by the glass or a bakery selling fresh slabs of schiacciata.
Top tip: Many of Tuscany’s vineyards offer cooking classes alongside tastings – perfect for the designated driver (and for the others to enjoy with a glass of Chianti).
8. Explore the ruins of Pompeii beneath Mount Vesuvius
When Mount Vesuvius erupted in 79AD the Roman city of Pompeii was buried under ash, preserving everything from bakeries and bathhouses to painted frescoes and cheeky, graffiti-ed walls. Today, you can wander along stone streets worn smooth by chariot wheels, past once-elegant villas and courtyards, and spot election slogans and love notes still scratched into the walls. And of course, it’s all watched over by the brooding figure of Mount Vesuvius, ever-present in the background…
Top tip: Pompeii is enormous so hire a guide or focus on one section properly, rather than trying to see everything in one go.
9. Take a boat across Lake Como
If you’re going to visit Lake Como, you may as well do it properly: sunglasses on, scarf tied and skimming across the water in a polished wooden Riva speedboat. The glamorous shoreline has long been a playground for Hollywood’s best movers and shakers and you can spend the day peering at the grand villas and their wedding-cake-tiered gardens, before cruising into Bellagio or Varenna for lunch on the shore.
Top tip: Ask your captain to swing past Villa del Balbianello. It’s one of the most spectacular and has starred in everything from Star Wars to James Bond – and you can even wander in the gardens.
10. Climb the dome of Florence’s Duomo
Florence has no shortage of masterpieces, but none quite top the scale of Brunelleschi’s extraordinary dome. Climb the narrow staircases that spiral up through the structure itself, squeezing past aged brickwork and vast, intricate frescoes, until you emerge at the top… and take a deep breath. Florence from up here spreads out in a terracotta maze in every direction, church towers punctuating the city and the Tuscan hills rolling beyond.
Top tip: Book your climb in advance. Daily visitor numbers are limited and the best slots disappear quickly.
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