How many trips to Italy is too many? I ask because, while putting together this list of 15 brilliant Italian holidays for 2026, I spoke to someone who had just returned from her first: to Puglia. It was wonderful, she told me, but she had “done Italy” now. There was no need to go again.
I could take every one of these trips this year — from sailing a tall ship in the Aeolian Islands to hiking in the Dolomites or just chilling on Sardinia’s best beach — and it still wouldn’t be enough. This is a country that requires a whole lifetime of exploration. I hope you’ll agree.
Lace up your walking boots to explore Italy’s most celebrated coastline the way locals have done for centuries. Accompanied by spectacular views, self-guided adventurers will hike the trails up into the Lattari mountains, avoiding the 31 serpentine miles of the SS163 — the coast road that nobody loves. You’ll walk along ancient mule tracks — the Sentiero degli Dei really is heavenly — through vineyards and lemon groves, to villages from pretty Positano to gorgeous green Ravello, exploring cliffside monasteries and nature reserves along the way. There’s a chance to visit the wonders of Pompeii, or stay local, eating in tiny agriturismi (don’t miss the delicious La Tagliata, in the hills above Positano; latagliata.com) and beachside stalwarts (Lo Scoglio always delivers; hotelloscoglio.com). The Amalfi Coast never fails to make the heart race — although this time, that’s as much about the ascents as the glorious blue views.
Details Seven nights’ B&B from £1,458pp, including luggage transport and some extra meals (inntravel.co.uk). Fly to Naples
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2. Eat your way around Emilia-Romagna
Tortellini comes from Emilia-Romagna
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With Italy’s national cuisine recently recognised by Unesco as an “intangible cultural heritage”, a trip along part of the ancient Roman route from Piacenza to Rimini, promising 60 miles of the finest food and wine, couldn’t be more timely. Taking in the historic Parma, Modena (home to Massimo Bottura’s world-beating Osteria Francescana restaurant) and Bologna, gastronomes can visit makers of Denominazione di Origine Protetta (DOP) classics that include parmigiano reggiano and grana padano cheeses, prosciutto di Parma and culatello di Zibello cured meats, balsamic vinegar and olive oil, plus the 50-plus Denominazione di Origine Controllata (DOC) wines in which the region delights (foodvalleytravel.com). There are trips to food markets, pasta-making classes, endless tastings and the opportunity to chat to dedicated producers — with the help of one of the tour operator Food Valley Travel’s knowledgeable guides — while staying at four-star hotels along the route. Combine it with a stay at the deeply stylish Casa Maria Luigia hotel (owned by Bottura and his wife, Lara Gilmore), in the Emilian countryside, for maximum indulgence.
Details Four nights’ half-board from £1,140pp, including daily guided excursions. B&B doubles from £350 (casamarialuigia.com). Fly to Bologna
3. Uncover the history of ancient Rome
The ruins of the Roman Forum
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Rome with a guidebook is fun, but to get the most out of this ancient city it’s worth splashing out on a real-life expert. Valeria Lenuzza and Paul Beston lead Peter Sommer’s group tour of the ancient city, unearthing the layers of history and legend behind the monumental architecture and the backstories behind pieces in the world-beating galleries and museums. They will introduce you to the Scipios, to Pompey and Cicero, to Julius Caesar and Mark Antony, and walk you through the works of Augustus, Claudius, Trajan, Hadrian and more. You’ll glimpse the lives of the Borgias, the Medici, Raphael and Michelangelo. Even the hotel — the four-star baroque Donna Camilla Savelli in Trastevere — has a rich history, and it’s all brought to life on this trip.
Details Seven nights’ B&B from £4,825pp, including daily guided tours and some extra meals (petersommer.com)
4. Cycle in southeast Sicily
Fans of Camilleri’s irascible Commissario Montalbano will already know — and love — Sicily’s baroque southeast, where eight gloriously overblown towns make up the Unesco world heritage site of the Val di Noto. This is a chance to get on your bike (electric or pedal-powered), riding up to 31 miles a day in a small group with Exodus to explore locations from Ragusa Ibla, rebuilt to dramatic effect after the great earthquake of 1693; to Modica, home of a deliciously granular type of chocolate produced to an ancient Aztec recipe; and Scicli, frequently used as a film set. There’s time to relax on the wild beaches of the Vendicari nature reserve before ending up in seaside Siracuse, described by Cicero as “the greatest Greek city and the most beautiful of them all”. You’ll stay in simple hotels and agriturismi along the way.
Details Seven nights’ B&B from £1,759pp, including tour leader, vehicle support and luggage transfers (exodus.co.uk). Fly to Catania
5. Rent a family villa in Puglia
Villa Mea has undergone an extensive restoration
SIMPSON TRAVEL
Once the holiday home of a noted northern industrialist, Villa Mea has undergone a five-year restoration project to emerge as a deeply stylish family rental with acres of veined marble and creamy linen, frescoed ceilings and Crittall windows. There’s entertainment for all, with an 18m outdoor pool, tennis court and ping-pong table, plus a pool house with a kitchen, gym and music system. With space for 12 (and a generous six bathrooms), Villa Mea can host multigenerational groups with a varied holiday wish list, whether that’s hanging out in the shade of the landscaped gardens, a trip to the beach at Porto Cesareo on the Ionian coast, or a visit to the glorious baroque towns of Gallipoli, Nardo and Lecce. Salento is a region still largely unknown to UK visitors — though the proliferation of new boutique masserie hotels (fortified agricultural estates) and the renown of its primitivo red mean that won’t be the case for much longer.
Details Seven nights’ self-catering for 12 from £8,124. Fly to Brindisi
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6. Soak up the history of art in Florence
The Palatine Gallery in Florence’s Pitti Palace
ALAMY
Florence is the cradle of the Renaissance, packed with work by the biggest of big hitters. The art and architecture of Michelangelo, Leonardo, Raphael, Giotto, Brunelleschi, Donatello, Masaccio and Botticelli were all nurtured here, and are the focus of Martin Randall’s group tour of the city, led by Dr Flavio Boggi and Desmond Shawe-Taylor, both experts in the Rinascimento. Accommodation is in the four-star Hotel Santa Maria Novella, with views onto the famous basilica, whose elaborate façade was completed by Leon Battista in 1470. Special access to hotspots including the Uffizi and Palazzo Pitti means visitors can dodge the crowds, and guides will direct you to locals’ favourite restaurants including Cibreo Trattoria — the sensibly priced but equally delicious sister to the fine-dining Cibrèo next door — and Trattoria Cammillo, a Florentine institution serving classics such as ribollita (a delicious Tuscan bean stew) and the hefty bistecca alla Fiorentina.
Details Six nights’ B&B from £3,060pp, including guided tours and some extra meals (martinrandall.com). Fly to Florence
7. Sail a tall ship in the Aeolian Islands
VentureSail’s Florette has plenty of watersports gear for exploring
The Aeolians, in the Tyrrhenian sea off Sicily’s northeast coast, are a volcanic group of seven sisters — Lipari, Vulcano, Salina, Panarea, Stromboli, Filicudi and Alicudi — of exceptional beauty. The best way to see them (avoiding the inevitable flight, train and ferry grind) is by boat. In this case, the classic wooden windjammer Florette, crewed by Ron and Nicole Haines, with their Spanish water dog, Lucy. You can enjoy the laid-back Aeolian lifestyle at your own pace, with sailing in the morning — Florette also has kayaks, stand-up paddleboards and snorkelling gear for guests — and afternoons free to explore the islands. Check out Lipari by Vespa, shop the upmarket boutiques of Panarea, book a tour and tasting at one of Salina’s excellent vineyards, or hike up to Vulcano’s sulphurous crater.
Details Seven nights’ half-board from £1,685pp (venturesailholidays.com). Fly to Palermo
8. Live la dolce vita on the Orient Express
Inside a cabin on La Dolce Vita Orient Express
The ritziest train in the world has launched a luxury Italian model, La Dolce Vita Orient Express — with design by the Milan-based Dimore Studio that celebrates 20th-century greats such as Gio Ponti and Gae Aulenti, and catering by the acclaimed chef Heinz Beck using ingredients local to every stop. Its apex offering is the Grand Tour (alternatives include the Truffle Route to Piedmont and the Northern Greens for the ultimate in golf), a five-day round trip from Rome, taking in the canals of Venice, the ancient cave dwellings of Matera, the coastal beauty of Taormina and the dark energy of Palermo. Stopping off in Italy’s most sensational — and sensual — locations, passengers will have time for free exploration, or a guided itinerary. It’s a luxurious way to travel, and that’s reflected in the ticket price.
Details Four nights’ full board from £14,500pp (orient-express.com). Fly to Rome
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9. Hike in the Dolomites
The famous Three Peaks of the Dolomites
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In the run-up to the Winter Olympics 2026, which will be part-based in Cortina d’Ampezzo, the Dolomites have come into focus. Yet in summer the mountains of this Unesco world heritage site are equally beautiful, with the enrosadira — an unearthly glow as the sun goes down — a particular treat. On this small group trip with Intrepid, walking up to nine miles a day on easy to moderate routes with a maximum elevation gain of 800m, you will experience the sheer peaks, deep green valleys and flower-filled meadows of this limestone mountain range in Italy’s northeastern corner, staying in the pretty town of Dobbiaco, close to the Austrian border. An experienced guide will lead hikes around the Tre Cime di Lavaredo, three peaks skirted by the most scenic trail in the Dolomites, and the Piramidi di Plata, a huddle of unearthly pyramids. You will refuel in village inns on hearty mountain food and picnic on local specialities.
Details Seven nights’ B&B from £2,115pp, including guided hikes and transfers (intrepidtravel.com). Fly to Venice
10. Sunbathe on the beach in Sardinia
Hotel Cala di Volpe
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Cala di Volpe tops the list of best beaches for many a Sardinian visitor, and no wonder: it’s a gorgeous little cove on the Costa Smeralda, one of the most beautiful (and costly) stretches of coastline in Italy, with water that’s a dazzling blue and sand an expensive white gold. The nearby Hotel Cala di Volpe has hosted entertainment royalty from Beyoncé and Jay-Z to George and Amal Clooney, but the waters are open to all — you don’t need to be a guest of the hotel to swim there. Nearby the Spiaggia del Romazzino is a family-friendly stretch of fine white sand with views out to the archipelago of La Maddalena, a designated national park and a haven for wildlife.
Details B&B doubles from £520 (marriott.com). Seven nights’ B&B from £2,769pp, including flights (elegantresorts.co.uk)
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11. Check into Italy’s best new hotel in Milan
A room at Rocco Forte’s Carlton Milan
Rocco Forte’s Carlton Milan, which opened in November 2025 after a £53 million refit, joins a handful of exceptional new hotels in this urban hotspot. No longer simply a destination for finance and fashion, the Lombard capital has shaken off its sombre image in recent years to become the second-most-visited city in Italy. The director of design Olga Polizzi has worked with the interior architects Paolo Moschino and Philip Vergeylen to create 71 sublime suites and rooms in contemporary deco style, while Fulvio Pierangelini — named the best chef in Italy by the Gambero Rosso guide — is at the helm of the fine-dining restaurant Spiga. The Carlton Bar, overseen by the super-mixologist Salvatore Calabrese, serves 1970s-influenced cocktails with a twist. Piña colada alla Milanese, anyone?
Details B&B doubles from £1,140 (roccofortehotels.com). Fly to Milan
12. Take a city break in Turin
Turin has gorgeous baroque architecture
ALAMY
The one-time capital of the unified Italy, Turin is a baroque beauty that gets more glamorous with age. It’s ideal for a winter break — eminently walkable, with 11 miles of elegant arcades to keep off the snow, more than 40 world-class museums, including the Museo Egizio (with the finest Egyptian artefacts outside Cairo) and the Museo Nazionale del Cinema, housed in a towering former synagogue. The city has given us not just Fiat, Juventus and Lavazza, but also the slow food movement: here you can feast on local truffles and bagna cauda (a dipping sauce made from anchovies and garlic), and drink barolo and vermouth — check out Michelin-starred Cannavacciuolo Bistrot for a modern take on Piedmontese cooking. The centro storico — an elegant sweep of Savoyard-style palazzi, curious churches, regal squares and art nouveau flourishes — offers caffè culture at its finest in the jewel-box Al Bicerin and Mulassano too. Stay at the stylish at the NH Collection Torino Piazza Carlina.
Details Two nights’ B&B from £274pp, including flights
13. Dive into little Lago d’Orta in Piedmont
Orta San Giulio sits right on the lake
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A kind of Como in miniature — and to my mind, infinitely lovelier — Lago d’Orta offers all the spectacle of the northern lakes without the crowds. A favourite with weekenders from Milan (who call her La Cenerentola, a Cinderella to her uglier sisters, Maggiore and Como), Orta has all the watersports you could wish for — kayaking, SUP, sailing, waterskiing, wakeboarding and windsurfing — along with a medieval lakeside piazza in Orta San Giulio lined with faded frescoes and atmospheric bars. In the centre of the lake, Isola San Giulio is a tiny island once — apparently — ruled by a dragon. It is now home to a handful of cloistered Benedictine nuns whose singing on misty Sunday mornings is audible on the mainland. Hire ebikes in Omegna for a lightning tour of the lake, and stay at La Darbia, self-catering apartments on the hillside in the middle of a nebbiolo vineyard.
Details Apartments from £430 (ladarbia.com). Fly to Milan
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14. Cruise the Venetian lagoon
A cabin on the Luxury Holiday Company’s Verona and Northern Italy cruise
UNIWORLD RIVER CRUISES
Venice is best seen from the water — and not just in a gondola. The SS La Venezia, at 110m in length and with 126 berths, is one of the privileged few allowed into the Venetian lagoon — and La Serenissima’s drama is reflected in the boat’s recent refurb, which doubles down on gilding and glamour. A seven-night cruise starts on land in Shakespeare’s fair Verona, staying at the five-star Due Torri hotel before boarding, when all the wonders of the lagoon are laid out before you: the Basilica di San Marco in an after-hours tour, the vineyards of Mazzorbo, the lace-makers of colourful Burano and the glass-blowers of Murano. The glories of Torcello — where the mosaics in Santa Maria Assunta are deciphered by an art historian — and the markets of lively Chioggia are for another day, while trips to Vicenza and Padua are also on offer, as well as on-board dinners with the captain, daytime classes and entertainment.
Details Nine nights, with seven full board on the SS La Venezia and two in Verona, from £3,654pp (theluxuryholidaycompany.com). Fly to Verona
15. Island-hop in the Pontines
The fishing harbour of the island of Ponza
ALAMY
The tiniest dots on the map in the Tyrrhenian Sea, the six Isole Pontine are the classy Romans’ holiday islands of choice. Ponza, the largest, where Odysseus was bewitched by Circe on his way home from burning Troy, still retains a kind of trippy magic. It lures you down hundreds of steps to its tight crescents of beach, or into the purple sea caves where divers search for treasures lost by long-ago pirates. Away from the ritzy boutiques of Piazza Carlo Pisacane, Ponza has a raw allure that is replicated in the wild coves and soaring rock formations of its neighbours, Palmarola and Zannone. Rent an outboard from Divaluna in Ponza’s colourful port, or take the hydrofoil to Ventotene, one of the greatest scuba spots in Italy, populated by friendly barracudas and giant groupers. Stay at the charming cliffside Hotel Chiaia di Luna.
Details Room-only doubles from £101 (hotelchiaiadiluna.com). Fly to Naples
Have we missed your favourite Italian destination? Let us know in the comments below
