Rich with historic buildings, fabulous hotels and unbelievable restaurants, the country’s easily accessible cities are a good place to start. Ambling through the streets of these open-air museums is one of the best holiday activities on earth; you’ll be ticking off some of the world’s key sights and stumbling into new finds. Gaze starry-eyed at Roman landmarks glamourised in classic Hollywood movies, marvel at Milan’s well-dressed denizens forever in a fashion parade, or escape Venetian crowds by hopping across the Lagoon to Lido island.
Alongside the obvious urban choices, there are also up-and-coming destinations to discover. A glittering display of mosaics and modern galleries makes Ravenna a magnet for art fans, while energetic Naples sizzles like one of its famous margherita pizzas.
Beyond busy centres, easy-to-reach rural areas, mountain slopes and sandy coastlines are options for a more relaxing getaway. Trains, planes, bike-friendly country roads and hiking paths connect the country, making it possible to pack a lot into a short period of time.
Whether rejuvenating at world-class spas or wild swimming in glassy waters, the north’s sub-Alpine lakes are an excellent choice for relaxation. Or for better beach weather, delve into Sardinia’s jewellery box of sapphire waters and amber sands.
Although it’s impossible to do everything in one go, treat these taster trips as antipasti for bigger adventures to come.
Explore, enjoy, and seize the moment — do as the Romans did.
Some of the world’s best bubbles can be sipped at Valdobbiadene
1. Vineyard touring in the Prosecco hills, Veneto
A more affordable alternative to champagne, Italy’s finest fizz has been the go-to for filling our flutes in recent years — although most Italians would balk at the sweet stuff on British supermarket shelves. The best bottles of prosecco remain in their homeland, cultivated on precipitous slopes 1,000 feet above sea level in a largely undiscovered wine region of the Veneto.
On this package, after flying in to Treviso, travellers will be taken by their private driver to taste Cartizze, the best bubbles with DOCG designation, at the family-run winery Bastia Rebuli Michele (bastiavaldobbiadene.it) in Valdobbiadene. Then on the sunny terrace of Osteria Borgoluce, a farm winery with rooms, dine on the likes of buffalo mozzarella with nettle cream, and gnocchi with the restaurant’s own mortadella (mains from £18; borgoluce.it).
Beyond the vines, at the foot of the Dolomites, take time to admire sweeping views from Asolo, dubbed “the town of a hundred horizons”, its pretty hillside buildings looking out towards Venice. Huff and puff to the ruins of the 12th-century medieval fortress La Rocca and have a bellini in the Villa Cipriani’s mahogany-walled American Bar, designed by the Harry’s Bar founder, Giuseppe Cipriani (villacipriani.it). You can hit the original Harry’s Bar, too, as the trip includes a night in Venice.
Details Four nights’ B&B from £1,550pp, including flights, transfers and wine tastings (wexas.com).
Convent of Saint Agostino, Matera
2. Unearthing secrets in Matera, Basilicata
Surviving centuries of human habitation — and several furious Bond car chases — Matera, one of the oldest continuously inhabited cities in the world, is a well-worn beauty. At night, lights sparkle like a galaxy of stars from the “sassi”, meaning stones, the warren of crumbling caves which house shops, hotels, cafés and the mind-twisting sculpture gallery MUSMA (free; musma.it). Sleep in the candlelit Sextantio Le Grotte della Civita, where a chapel has been converted into a dining room and caves into bedrooms, and splash out on Michelin-starred interpretations of Basilicata’s underrated cuisine, such as sweet liquid ricotta ravioli with sea urchins, cinnamon and yellow tomatoes, at Vitantonio Lombardo (five courses £115; vlristorante.it).
The city is a maze of gravity-defying churches and viewpoints. Climb to the terrace of the Fontana dell’Amore statues for a view of the Saint Mary of Idris church chiselled into a rocky peak. A suspension bridge crosses a ravine to reach the “rock” churches hewn into a gorge. The Crypt of the Original Sin, with its 1,000-year-old frescoes, is a 15-minute drive outside Matera and well worth a visit (£8.50; book in advance at criptadelpeccatooriginale.it).
Details Four nights’ B&B from £1,999pp, including flights, transfers and guiding (abercrombiekent.co.uk)
The pool at Hotel Excelsior Venice Lido Resort
3. Slowing down the pace in Venice
La Serenissima has a reputation for overcrowding, especially in the summer months, but even during the busiest periods there are pockets of calm. A 15-minute vaporetto ferry ride across the lagoon, on the seven-mile barrier island of Lido, the beach and rolling dunes inspire contemplation. The best stretch of sand belongs exclusively to the Golden Age glamour-puss Hotel Excelsior Venice Lido Resort, where classic Italian cabanas are available for hire. Attracting celebs since it opened in 1908, it’s now the official host of the Venice Film Festival.
Rise early to look for birds along the Oasis of Alberoni nature reserve, in the south of the island, ferry-hop to Venice’s sights and its other islands, and bumble through the streets of the colourful fishing village Malamocco — a well-kept Venetian secret. Wind down with a Campari spritz and mixed antipasti of meatballs, grilled calamari and anchovies dripping in olive oil at Da Cri Cri e Tendina; sit at the wooden bar with locals or on the pavement (mains £13; +39 041 526 5428).
Details Three nights’ B&B from £671pp, including flights (britishairways.com)
Tuck in at Il Granaio dei Casabella’s rustic restaurant
4. Making tracks along Cilento’s coast, Campania
As heavenly as Amalfi’s popular Path of the Gods seaside hiking route, but with far fewer worshippers, the Path of the Sirens runs along a neighbouring stretch of coast in wild and rugged Cilento. Lured by hypnotic songs, multiple sailors crashed into the rocky ridges in this area, which is still yet to register on mass tourism radars.
Fly to Naples, then take a 75-minute train ride (about £7) to Paestum, home to near-complete Doric Greek temples in the Paestum Archaeological Park (£10.50; museopaestum.cultura.gov.it) and water buffalo farms producing the finest mozzarella. Using music and homeopathic remedies to improve their beasts’ milk yields, organic farm Tenuta Vannulo (vannulo.it) runs tours and tastings and sells excellent chocolate made with buffalo milk.
Continue the rustic theme by staying at Il Granaio dei Casabella, a barn transformed into a simple hotel opposite one of Paestum’s original city gates. Catch a local train to Agropoli (about £2.50), the best base for coastal hikes.
Details Four nights’ B&B from £575pp, including baggage transfers (macsadventure.com). Fly to Naples
Forte Village in Sardinia has high-tech spas and great restaurants
5. Get active in Sardinia
Spending time on Sardinia’s south coast can mean hiking to hidden beaches and a 19th-century lighthouse along Capo Spartivento, hiring a bike to head to the Roman ruins of the ancient city Nora, and discovering Gutturu Mannu Natural Park, a trekker’s playground of canyons, waterfalls and rocky spires. For a short break it’s easiest to be based in one hotel. Between seasons, footballers come to rejuvenate at Forte Village, a mini empire of a resort with high-tech spas, sports facilities and fabulous restaurants tucked behind wispy pine trees, near Cagliari. Beyond flexing muscles, burning calories and raising heart rates, there are opportunities to learn new skills: join boxing academies taught by champions, scale an indoor climbing wall, or perfect pirouettes and salsa shimmies at a dance school. Then, to heal any aches and pains, there’s a world-class circuit of water therapy pools at the Acquaforte Thalasso & Spa.
Details Four nights’ half-board from £739pp, including flights (britishairways.com). Bike hire from £45 a day
Walk among living history in Syracuse, Sicily
6. Culture and set-jetting in Syracuse, Sicily
Many parts of Sicily would be wonderful for a short break, but Syracuse, on the southeast coast, is easy to reach from Catania (a three-hour hop from the UK). It’s the island’s archaeological showpiece, where you can peel away several layers of history; Greeks, Romans and 18th-century Spanish aristocrats all left their imprint on sun-soaked Syracuse. Key sights take centre stage in the new Indiana Jones and the Dial of Destiny film, released in June. Do your own historical detective work by exploring temples and tombs more frayed and frazzled than Harrison Ford’s own ageing façade.
Discover the Greek Theatre (where classical performances still take place from May to July; comune.siracusa.it), the Roman theatre and catacombs at the Archaeological Park of Neapolis (£10; parchiarcheologici.regione.sicilia.it). Refuel with arancini (deep-fried rice balls) at Bar Midolo (£2.50; barmidolo.it) in the old town and blood orange granita at Bar Caprice (£2; capricesambito.com) in the nearby village of Belvedere.
Base yourself at Hotel Gutkowski, close to the sea and within easy walking distance of Siracuse’s old town, and gaze at Mount Etna on the horizon.
Or for a deeper understanding of the past, book a package and stay a little longer to combine it with the baroque towns of Ragusa, Noto and Scicli on a self-guided cycle tour, pedalling through Inspector Montalbano country and staying at local guesthouses, with luggage transported separately.
Details Six nights’ B&B from £1,360pp, including bike hire and GPS navigation (inntravel.co.uk). B&B doubles at Hotel Gutkowski from £80 (Guthotel.it). Fly to Catania
Beaches lie below soaring white cliffs in Calabria
7. Bay hop along the coast of Tropea, Calabria
Scuffed and unpolished, the toe of Italy’s boot is still a shining beauty. Calabria’s coastline is less flashy than the riviera resorts of Amalfi or the Cinque Terre, and has earthy appeal: voices are louder and characters larger than life. You’ll laze on beaches below soaring white cliffs and could climb to Santa Maria dell’Isola, a Benedictine sanctuary perched on a rocky peninsula. Explore bays only accessible by sea along the Coast of the Gods by renting a boat (from £97 per half day; noleggiobarchetropea.it). Capo Vaticano, a cove six miles south, is like a real-life aquarium for snorkellers and divers.
A good base for your explorations is the adults-only Villa Paola, a grand palazzo that was originally a 16th-century Franciscan convent and comes with a surprisingly humble price tag. Tomatoes and red onions — a Tropean speciality — grow in the gardens and are served in the on-site restaurant De’ Minimi in dishes such as tortelli filled with Tropea red onion and blue sheep-milk cheese in hen broth (mains from £20). Nicknamed the stone city, the 1,000-year-old Caves of Zungri (a 12-mile drive from Tropea) provide cool shelter from the sun.
Details B&B doubles from £250 (villapaolatropea.it). Fly to Lamezia Terme
8. Designer shopping in Milan
Cobbled streets serve as catwalks in one of Europe’s most stylish cities, where fine cloths have been spun since the 16th century. A time-frozen antique of mahogany and crystal, Prada’s original store in the glass-covered Galleria Vittorio Emanuele II arcade is as much an institution as the Duomo or Da Vinci’s The Last Supper. If you can’t afford the price tags, rummage through vintage finds at Cavalli e Nastri in the bohemian Brera district (pick up a 1970s Missoni scarf for £100) or cut-price couture at consignment store Bivio (there are three branches in Porta Ticinese and Porta Venezia).
Keep on trend with a stay at the fashionable new Portrait Milano, part of the Lungarno Collection, owned by the Ferragamo family. Housed in one of the world’s oldest seminaries, the property overlooks the new Piazza del Quadrilatero, packed with restaurants and boutiques: the first Italian outpost of Riccardo Giraudi’s hit Beefbar brand is a meaty proposition (mains from £18; beefbar.com) while SO-Le Studio stocks Maria Ferragamo’s jewellery collections (so-le-studio.com).
Details Room-only doubles from £869 (lungarnocollection.com). Fly to Milan
Rooms at Lefay Resort & Spa look out over Lake Garda
9. Spa break in Lake Garda, Brescia
Inspired by the Greeks, the Romans were the first to develop spa resorts as centres for treating wounded soldiers. Anyone battling the stresses of urban living today will find relief in the healing waters and thalassotherapy pool at the lakeside Lefay Resort & Spa, in northern Italy’s popular lakes region. After examining energy levels, therapists prescribe a programme of massages, cryotherapy treatments and bathing rituals based on a combination of Western science and Chinese medicine. Dine on fish and plant-based dishes at the health-conscious on-site restaurant Gramen or grab snacks on a stroll along the promenade in Gargnano.
For a breath of fresh Alpine air, follow a therapeutic running trail winding through gnarly trees and fragrant Mediterranean plants in the resort’s grounds, or wander into the surrounding Alto Garda Bresciano Park. An easy hike along dusty mule tracks through vineyards and cypress forests reaches the contemplative, cliffside Hermitage of San Valentino.
Details Three nights’ full board from £1,539pp, including flights, transfers and programme (healingholidays.com)
There are plenty of swimming spots dotted around Lake Orta
10. Wild swimming in Lake Orta, Piedmont
Of all Italy’s sub-Alpine lakes, Lake Orta lays claim to being the clearest and cleanest. Choose to take a dip from several pay-to-enter beaches along the eastern shore, equipped with loungers, play areas and snack stalls. Sandy Gozzano is bathed in day-long sunshine, while Miami beach has canoes and paddleboats for rent (both cost £5 for the day); for free access, try the pier at Ortello.
Most bars and restaurants cluster around the medieval village of Orta San Giulio. Taverna Antico Agnello serves Piedmontese classics (mains from £16; ristoranteanticoagnello.com) and Villa Crespi’s gourmet restaurant has been awarded three Michelin stars (villacrespi.it/en; mains from £53).
For romantic isolation, stay in the quiet village of Pella on the western shore at the contemporary Casa Fantini boutique hotel, where each room has a terrace overlooking the glassy water. Boats run from the public dock to the lake’s showpiece island Isla San Giulio and its photogenic basilica.
Details Three nights’ B&B from £1,038pp, including flights and car hire (kirkerholidays.com)
Hotel Palazzo Bezzi is a boutique hotel with a panoramic rooftop
11. Byzantine mosaics in Ravenna, Emilia-Romagna
As sparkly as a clear sky at night, this mosaic-clad treasure trove became one of the most important cities in the world in 402AD when it was declared the capital of the Western Roman Empire. Ravenna is home to some of the finest Byzantine interiors, which miraculously survived aerial bombardment in the Second World War. Get the full story from local historians on a guided tour of the city, located a few miles inland from the Adriatic, visiting the kaleidoscopic Basilica di San Vitale (an inspiration for the Hagia Sophia of Istanbul) and the ten-sided Mausoleum of Theodoric the Great.
Skip forward a few centuries at studios and galleries where modern artists have taken the art of making mosaics to new levels: the Koko Mosaico studio offers classes and short courses for beginners (kokomosaico.com), while the city’s Art Museum (mar.ra.it; £4) has a permanent collection of works from the 1950s onwards. Stay next door at the elegant Hotel Palazzo Bezzi and head to its panoramic rooftop for sunset.
Details Three nights’ B&B from £1,595pp, including flights, transfers and guiding (coxandkings.co.uk)
Visitors to Umbria will cycle through Italy’s “green heart”
12. Freewheeling through Umbria
One of the first roads ever constructed, the Via Flaminia connected Rome with the agricultural areas of the north. Steer your own 21st-century chariot on a road trip passing through part of the route, travelling between vineyards, trattorias and historical sites in Italy’s “green heart” on an e-bike. Admire turrets guarded by sentinels of tall cypress trees in the Niccone Valley and stop at the medieval town of Montone for a meal at the celebrity chef Giancarlo Polito’s gourmet restaurant La Locanda del Capitano (ilcapitano.com; mains from £20).
Continue along a pilgrimage route towards the birthplace of St Francis of Assisi, a textbook perfect medieval town framed by a ripple of hills and thick forest. Filled with enough artwork to rival a national gallery, the Basilica di San Francesco in Assisi is the top attraction. But save time to wander through olive groves surrounding the tiny San Damiano church, where the nature-loving saint wrote his famous ode to earth and animals. Along the way you will stay in a variety of rural hotels and inns.
Details Five nights’ B&B from £975pp, including e-bike hire and luggage transfer (cycling-for-softies.co.uk). Take the train to Florence via Paris on Eurostar
Follow in Audrey Hepburn’s footsteps to the Trevi Fountain
13. La dolce vita in Rome
Featured in countless Hollywood movies, the Eternal City shimmers on the big screen. But nothing compares with seeing it in real life. Make a tour of iconic locations on a new Sightseeing & Savour Experience offered by the Sofitel Roma Villa Borghese. Follow in Audrey Hepburn’s footsteps to the Trevi Fountain and Spanish Steps; revive La Dolce Vita in the cafés of Via Veneto; and explore the Baths of Caracalla, where a giraffe magically disappears in Paolo Sorrentino’s cult hit La Grande Bellezza.
The hotel’s restaurant, Settimo, has designed a tasting menu of dishes inspired by cinematic icons. Eat a toasted pistachio parmesan arancini from The Godfather, along with saltimbocca alla romana (veal cutlets), Dino’s favorite dish in Three Coins in the Fountain.
Burn off excess baggage with a walking tour exploring the work of Rome’s biggest A-lister, Michelangelo. Beyond the Sistine Chapel, find lesser-known examples of his work in a chapel at Castel Sant’Angelo and in the Piazza del Campidoglio. There’s also an option to run between stops on the tour (from £71pp; archeorunning.com).
Details Three nights’ B&B from £3,200 including a film-inspired meal (all.accor.com). Fly to Rome
Agricultural Puglia is known for its olive oil
14. Feasting in Puglia
Olive oil is liquid gold in Italy, making Puglia — where 50 per cent of it was once produced — a prized culinary region. Estimated to be up to 3,000 years old, many of the gnarled trees are regarded as national monuments and some are even up for adoption to drum up financial support and safeguard their future.
Taste the finest oils in masserie (farms) around Ostuni, a white-walled city surrounded by olive groves tumbling towards the sea. Set in an 18th-century farmhouse, Masseria Valente runs tastings and tours (£31.20; civitatis.com).
Learn how to make the pane di altamura (bread), which must have a crust a minimum of 3mm thick, at the Martina Franca Masseria (from £80pp; terrachevive.com) before heading to the gleamingly white town of Alberobello. Stay the night in a trullo, a dry-stone hut with a conical roof; Trulli e Puglia Resort has restored houses in the historical centre (trulliepuglia.com).
Details Four nights’ B&B from £574pp, including activities and one dinner (untravelledpaths.com). Fly to Bari
15. Opulence and pizza in Naples
Loved and loathed by Italians, the birthplace of pizza is deliciously romantic with a gritty crust. While opulent houses and museums decorate upscale Vomero, the old town is a chaos of noisy Vespas roaring through narrow streets. Spanning 4,000 years of history, many churches, buildings, palazzos and catacombs remain hidden from view; take a rare opportunity to snoop behind closed doors on guided tours and themed walks during the Maggio dei Monumenti festival in May (programme tbc; visitnaples.eu).
A month later, the Pizza Village festival is celebrated along the Caracciolo promenade — although you’re never far from a freshly made margherita; no-frills L’Antica Pizzeria da Michele serves the best (pizzas £4; damichele.net). And for a true taste of street life, stroll along Spaccanapoli, stopping at San Gregorio Armeno to watch artists crafting intricate nativity cribs — known as presepe — year-round.
Towering above the city, Mount Vesuvius and its trails can be reached via the Circumvesuviana train from the city centre (£9; parconazionaledelvesuvio.it). If you’d rather not hike, lie back and admire the view from glass-walled suites in the smart water-side hotel Romeo Napoli.
Details B&B doubles from £276 (romeohotel.it). Fly to Naples
Velona’s Jungle is a luxury B&B in Florence
16. Cultural highs in Florence
Florence is ever more crowded in summer so you need a really local experience to scrape the surface. Enter Veronica Grechi, owner of Velona’s Jungle, a luxury B&B with the kind of decor you’d find in a posh hotel (Christian Lacroix textiles on the walls, for starters), paired with next level personal service. A born-and-bred Florentine, she’s obsessed with her city. You’ll find carefully curated artisan jewellery in the lobby, 18th-century furniture from her antique dealer grandfather’s collection in the rooms, and bathroom tiles that recreate Palazzo Pitti’s famous façade. Veronica can organise cooking classes in the Fiesole hills, or point you in the direction of her favourite no-nonsense trattorias. She’s just a five-minute tram ride from the airport — and a romantic 20-minute walk along the Arno to the Ponte Vecchio.
Details B&B doubles from £221 (velonasjungle.com). Fly to Florence
Spring is the perfect time of year to take in Tuscany’s rolling hills
17. Enjoying Tuscany’s landscapes
May is the perfect time to visit the Val d’Orcia, the Tuscan landscape that launched a thousand coffee table books. The rolling hills are fuzzed in acid green, wild poppies and broom bushes flower by the roadside, and the tiny towns aren’t yet crammed with the summer crowds. Pienza is the place to stay — it was dubbed the “Ideal City” by Pope Pius II, who rebuilt his home town in the 15th century in classic Renaissance style, and its perfectly proportioned palazzos balance on a hill overlooking one of Italy’s greatest landscapes. Rent a car or an e-bike to dive into it, wiggling along cypress-studded avenues, cutting across hills on strade bianche — dirt roads, coloured off-white by the clay soil, and rolling up and down past thermal springs and more Renaissance hill towns towards Monte Amiata, the dormant volcano embracing the valley. June, when the wheatfields blaze yellow, is another lovely time to visit, as is October, the month for spicy new olive oil, fresh chestnuts and spectacular sunsets. Stay at La Bandita Townhouse, a former convent turned into a hotel.
Details B&B doubles from £261 (furtherafield.com). Fly to Perugia or Florence
Hop between five fishing villages in Cinque Terre
18. Simple pleasures in Cinque Terre
The Liguria coastline has entranced Brits since the days of the Grand Tour. Today, tourism is focused on Cinque Terre — five tiny fishing villages etched into the cliffs near La Spezia — but you can’t go wrong anywhere in the region, since it’s one long curved slice of coastline. To keep things simple, base yourself in Genoa — it’s an underrated city of medieval alleyways, swaggering Renaissance palazzos and relatively few tourists. You already have coastline here. An easy 40-minute walk from the centre along Corso Italia, with belle epoque villas one side, the sea the other, gets you to the fishing village Boccadasse, where at GE8317 you can feast on fresh seafood netted that morning by the owners, the local fishing cooperative. In the suburb of Nervi, 15 minutes by train, the grounds of fancy villas have been turned into a beautiful seafront park, with restaurants and bars cantilevered above the water. Trains continue south along the Riviera di Levante — you can get to Cinque Terre and that other tourist hotspot Portofino for the day, but if you’re after something calmer, try Camogli, a peaceful fishing village tucked into the coastline on the other side of the Portofino promontory. Straddling the line between sleepy and chic, it’s a haven for Milanese weekenders.
Details B&B doubles from £100 (hotellenuvole.it). Fly to Genoa
Additional reporting by Julia Buckley
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