The 30 greatest Italian holidays
Ah, Italy. It is a perennial favourite, of course, with its cradles of culture – Venice, Rome and Florence – attracting the bulk of tourists. But there is so much more to be discovered away from the big-hitting highlights.
This year, there’s an increased focus on outdoor activities, with hiking and cycling holidays popular choices. While Tuscany’s rolling hills have long been the go-to rural escape for British travellers, they are only part of the story. Hit TV series such as The White Lotus have put Sicily firmly on the tourist map, and there is a wealth of experiences to be had, including sailing the volcanic Aeolian Islands on a classic wooden windjammer.
And while we have listed some firm favourites in our list, we hope to inspire you with getaways that are not your conventional Italy holiday, too, from learning about Ladin culture in the German-speaking Alta Badia region to horse-riding through the wilds of Molise in central Italy.
Prices and temperatures soar in July and August so, if you can, try and visit outside these months. If you can only travel then, but don’t like the idea of overly hot weather, make for the mountains instead, where altitude will give you a welcome respite from the stifling heat further south.
Abruzzo
Wild wanders
This east-coast region is home to some of Italy’s wildest landscapes – the Gran Sasso and Majella are among the highest massifs in the country outside the Alps, with wild animals including wolves, endangered Marsican brown bears and chamois roaming the dense beech forests. This five-night tour combines e-biking and walking, taking visitors across the Majella and Gran Sasso National Parks along quiet paths that meander through forested valleys and high plateaus, stopping off to refuel with hearty mountain fare.
The five-night trip with The Slow Cyclist costs ￡3,250pp, and includes airport transfers, tour guides, accommodation, meals, all activities, e-bikes and helmet hire. Flights not included.
Umbria
Saints and sights
2023 marked the start of three years of celebrations to celebrate the life of Saint Francis of Assisi, who left an indelible mark on Umbria, with no shortage of monasteries, shrines and pilgrimage routes associated with his life. This trip includes Francis’s birthplace of Assisi, taking in the spectacular frescoes of the Basilica di San Francesco along with the Basilica di Santa Maria degli Angeli, where Saint Francis announced he would cultivate poverty, founding the Franciscan movement. The holiday also includes a wine tasting tour and a leisurely boat ride across Lake Trasimeno, where Hannibal famously defeated the Roman army during the Second Punic War.
Ramble Worldwide’s Sights and Delights of Umbria trip costs from ￡1,479 pp including seven nights’ half-board with one lunch, wine with evening meals, flights, transfers, local transport, guided walks, wine tasting tour and lunch at a local vineyard.
Molise
Horseriding heaven
Sleepy, mountainous little Molise, snugly tucked away in central Italy, remains well off the tourist radar – and there’s no better way to explore this rugged region than on horseback. A recently launched trail ride follows the region’s tratturi, ancient sheep and cattle-driving routes used by shepherds and herders to move their flocks from high pastures to the lowlands in winter.
The Tratturi Altomolise Trail with Far and Ride costs from ￡950pp including six nights’ accommodation in shared rooms, all meals, wine and beer with lunches and dinners, five days of riding and transfers to/from Isernia train station. Flights not included.
Positano
Boutique rooms
Franco Zeffirelli was one of Italy’s greatest opera and film directors, whose adaptations of Shakespeare tragedies brought him international fame. His former home is now a boutique hotel, set in in a dramatic location perched on a cliffside above Positano on the Amalfi Coast – all lush gardens, secluded terraces and hidden pools shaded by tropical plants. The villa houses Zeffirelli’s memorabilia and family heirlooms, with original sketches for his sets also on display.
Treville Positano (00 39 089 812 2401) offers doubles from ￡675 on a B&B basis. Plan the perfect holiday on the Amalfi Coast with our guide.
Pompeii
Astounding archeology
Earlier this year, artworks depicting scenes from Greek mythology were uncovered in Pompeii, while last year the site’s Casa dei Vettii reopened after 20 years’ restoration, revealing head-turning frescoes and offering an incredible insight into Roman domestic life. As well as Pompeii and nearby Herculaneum, this tour includes a visit to Paestum, an ancient Greek city on the Tyrrhenian Sea where you can admire beautifully preserved Doric temples.
Travelsphere runs eight-day trips from ￡1,424pp, including return flights, tour guides, accommodation and meals.
Rimini
On your bike
The 111th edition of the Tour de France is set to host its Grand Départ on Italian soil for the first time this year, with the opening stage from Florence to Rimini. To mark the occasion, a new self-guided cycling holiday in Emilia Romagna takes biking enthusiasts from Parma to Modena, with a leisurely itinerary (complete with luggage transferred ahead by road) designed to allow time to take in the sights and refuel with local specialities along the way.
Inntravel’s six-night Flavours of Emilia Romagna is priced from ￡1,065pp based on two sharing, including B&B accommodation, bike hire, route notes and maps, GPS navigation, luggage transfers, and a guided visit to a balsamic vinegar producer with tasting. Electric bikes available for a supplement of ￡33pp. Flights not included.
Verona
Operatic immersion
The Arena di Verona Opera Festival has an incredible programme of events taking place throughout the summer, from operas to other musical performances by world-renowned artists. Two dedicated arrangements offer a novel way of experiencing the event – one with backstage passes to soak up the vibes before performances begin, the other with a Michelin-starred meal on the Arena’s Star Roof before taking front-row seats.
A three-night trip with Citalia costs from ￡699pp, including return flights, three nights on a B&B basis, a night at the Arena di Verona and private transfers. The additional Michelin-starred dining experience is priced at ￡995 pp and includes a gourmet dinner with wine and front-row seats; the Backstage VIP pass experience is priced at ￡475 pp and includes stall seats.
Sicily
Nature and culture
Italy’s largest island has been in the spotlight recently, its arresting landscapes the setting for episodes of comedy-drama series The White Lotus. Its capital, Palermo, is abuzz this year as it celebrates the 400th anniversary of the Festino di Santa Rosalia, with scores of events held throughout the year. The central focus is the historical parade on July 14 and 15, when the saint’s statue is carried from the city’s Norman Palace to the seafront aboard a lavishly embellished handcrafted float. The parade culminates in a spectacular fireworks display over the city.
Villa Igiea offers rooms starting from ￡469 per night on a B&B basis. Plan the perfect holiday in Sicily with our expert guide.
Le Marche
Open-aired arias
Named 2024 Capital of Culture, the Adriatic coastal town of Pesaro in the Marche region has a long (and strong) musical tradition, with over 80 musical festivals held annually. The most prestigious is the Rossini Opera Festival in August (the city is the birthplace of the composer), although it’s not only Pesaro that excels in operatic tradition – the Marche’s Macerata Opera Festival celebrates its 60th anniversary this summer with Norma by Vincenzo Bellini, one of the first operas staged in the town’s open-air neoclassical arena.
Scott Williams’ latest addition to its portfolio is Casa Aria, set in the Marche countryside. Sleeping up to 10 in six bedrooms, it comes with a panoramic swimming pool, sauna and steam room, with prices starting from ￡8,685 per week.
Florence & Venice
Arts and crafts
A recently launched foundation helps visitors scratch beneath the surface of two of Italy’s greatest art cities, introducing them to Florence and Venice’s hidden artisans. The Place of Wonders seeks to safeguard and promote artistic craftsmanship, providing exclusive access to family-run workshops, from porcelain-making ateliers and historic workrooms producing luxury cashmere in Florence to lampwork and jewellery studios in Venice.
Experiences are based on voluntary donations that go towards funding full scholarships for Italian craft students. In Florence, visits can be organised through The Place Firenze, where rooms are priced from ￡580; in Venice, through Londra Palace Venezia, where rooms are priced from ￡555. Plan the perfect trip to Florence with our expert guide.
Puglia
Architecture in style
Occupying the heel of Italy, Puglia has increasingly been on visitors’ radars in recent years, and little wonder – its whitewashed villages, Baroque architecture and powdery beaches with turquoise waters are a major draw, as is the region’s cuisine, heavily influenced by the region’s former Greek and Spanish rulers. The Apulian masserie (farmhouses) and famous trulli, distinctive conical buildings built as temporary storehouses or dwellings, have been converted into chic guesthouses and luxury hotels.
In partnership with StayOne, Mandarin Oriental Exclusive Homes has launched a couple of new holiday homes in Puglia this season, including the ten-bedroom Masseria Pistola, which combines original architectural features, including conical trulli ceilings and gable-roofed arches. Prices start from ￡1,430 per night.
Tuscany
Family adventures
In the heart of Tuscany lies the WWF-affiliated Oasi Dynamo nature reserve, harbouring rare species of plants and providing a rich habitat for wildlife including deer and wolves. Children can swoosh across a lake on a zip line and get involved in hands-on sustainable activities from a new beekeeping experience to wildlife tours, paper workshops using plants, leaves and seeds, and sensory activities, including discovering the sounds of nature and learning how to obtain ink and colours from the natural environment.
The eight-day group trip with Large Minority is priced from ￡2,264pp based on two people sharing and travelling together in one Piaggio Ape, and includes breakfast and two dinners. Flights not included. Plan the perfect holiday in Tuscany with our guide.
Northern Italy
Three-wheeled foray
First introduced to Italy’s roads over 75 years ago, the iconic, three-wheeled Piaggio Ape has become a symbol of Italian way of life, its whirring and rumbling sound as distinctive as its shape. This adventurous tour is aimed at travellers, whether solo or in small groups, who want to explore the country behind the wheel of an Ape, combining adventure, fun and food in four of Italy’s northern regions. A little competitive streak is an optional bonus – there are challenges along the way – and there is the chance for teams to meet up at pre-booked hotels to share travel tales.
The eight-night group trip with Large Minority is priced from ￡1,500pp, based on three travelling together, including breakfast and two dinners. Flights not included.
Friuli-Venezia Giulia & Veneto
Ham and history
Tucked away in Italy’s north-eastern corner, hugging Slovenia and a little stretch of Austria, Friuli Venezia Giulia is often overlooked in favour of neighbouring Veneto. Along with some of Veneto’s highlights outside of Venice, this new trip takes in Friuli’s Trieste, an elegant Adriatic city that was once the Habsburg Empire’s only port. The trip also includes a visit to the town of San Daniele del Friuli, renowned for its soft, buttery prosciutto that some would say edges the better-known prosciutto di Parma for quality and taste.
Cox & Kings’ eight-day fly-drive Beyond Venice: Veneto and Friuli trip is priced from ￡1,975 and includes flights, accommodation, one dinner, car hire and guides.
Sardinia
Making a splash
Porto Flavia in southern Sardinia is an extraordinary sight: a 1920s port terminal carved into the rockface along the Masua coastline. You can admire it from the water as you take part in a diving or snorkelling tour, travelling by boat from the port of Portoscuso to Pan di Zucchero, a towering sea stack whose underwater white limestone reefs are coated in sponges and inhabited by rich marine life.
Sardinian Places offer holiday stays in Southern Sardinia, with seven-night B&B packages starting from ￡999 including flights and private transfers or car hire. A half day diving tour with Ajoo Dive costs from ￡90 (snorkelling trips from ￡43), and includes boat transfers, guide and all diving equipment. Plan the perfect holiday in Sardinia with our guide.
Tuscany
Fitness al Forte
Nearer to Corsica than Tuscany, Capraia is the remotest island of the Tuscan Archipelago, and its only volcanic island, with steep cliffs dropping into deep blue waters home to groupers, barracuda and amberjack – there’s great snorkelling and diving to be enjoyed. An exclusive new fitness retreat immerses visitors into the island’s rugged scenery, with open-air lifting, yoga, hiking and breath work, complete with organic meals prepared by experienced chefs.
Wild Fitness retreats start at ￡2,674 per person per week at Forte San Giorgio, a listed national moment that has been converted into a sleek island retreat with 11 bedrooms, terraces for sunbathing, and two infinity pools. The fort is also available for exclusive buy-out hire.
Rome
Roman Jubilee
It’s over 70 years since Audrey Hepburn and Gregory Peck zipped around the cobbled streets of Rome on a Vespa in the iconic rom-com A Roman Holiday. Now is the time to explore the Eternal City before pilgrims descend next year for the 2025 Vatican Jubilee. The beginning of the jubilee is officially marked later this year on December 24, with the opening of the Holy Door of St Peter’s Basilica.
Onefinestay offers a range of carefully curated holiday rental apartments and homes in the capital, with prices starting from ￡260 per night. A 24/7 concierge service is available to all guests, with services including private chefs and babysitting services. Plan the perfect trip to Rome with our expert guide.
Emilia Romagna
A foodie foray
This region is Italy’s foodie heartland, the home of Parmesan cheese, Parma ham, balsamic vinegar and lasagne. This gastronomic tour in the company of chef, broadcaster and food writer Valentina Harris includes a pasta-making class, visits to local markets, artisans and food producers complete with behind-the-scenes tours, along with cultural trips to galleries and museums, refuelling here and there with hearty meals at traditional restaurants.
Kirker offers the Italy’s Gastronomic Heart tour from ￡2,689pp for five nights, including return flights, accommodation on a B&B basis, two lunches and three dinners and all entrance fees.
Calabria & Basilicata
Scenic drives
Occupying the toe of Italy, sun-kissed Calabria remains well off the beaten track. A new self-guided road trip introduces visitors to the region’s rich heritage, driving along wild stetches of the rugged Ionic coastline, taking in historical sites, powdery white sand beaches and sweeping sea vistas before crossing into Basilicata, home to the otherworldly troglodyte settlement of Matera.
Wexas offers a 12-day self-drive trip from ￡3,995pp, including return flights, accommodation on a B&B basis, 12 days’ car hire, three half-day private guided tours and a private home hosted dinner in Bari.
Lucca
Concerts galore
This year marks the 100th anniversary of composer Giacomo Puccini’s death, with musical celebrations and events held in his honour in his native Lucca. The Puccini Festival, which celebrates its 70th edition, commemorates the occasion with some of his most loved operas, including Tosca and Madama Butterfly. If contemporary tunes are more your musical flavour, the Lucca Summer Festival hosts international big names, with an exclusive view of the main stage from the Champagne Rooftop of the Grand Universe Lucca.
Double rooms at Grand Universe Lucca, Autograph Collection start from ￡220, room only.
Turin & Milan
Eye for design
Turin’s Fiat Lingotto factory was inaugurated 100 years ago, its iconic rooftop track famously featuring in the harum-scarum police chase in ‘The Italian Job’. This trip traces the development of Italian design from the turn of the 20th century to the present day, with visits to iconic buildings and access to private collections. Tours are led by expert lecturer Dr Philippa Joseph.
Martin Randall Travel (0208 742 3355) offers the Modernism in Turin and Milan tour from ￡3,570pp and includes flights, accommodation, one lunch, four dinners, travel by private coach, all admissions and the services of the lecturer and tour manager. Plan the perfect trip to Milan with our guide.
Lake Como
Off-the-beaten lake
Lake Como’s iconic Villa d’Este remains open once again this year throughout the autumn and winter, paving the way for an extended lake season. December is a magical time to visit, with the gardens – listed as a National Monument – bedecked with fairy lights in a spectacular display, and a cosy winter glasshouse where you can sit back with winter-themed cocktails as you take in panoramic lake views. The hotel’s new Snow Dream adventure whisks guests by helicopter to some of the Alps’ best ski resorts for a day on the slopes accompanied by an expert guide.
Doubles at Villa d’Este start from ￡1,100. Prices for the Snow Dream adventure available upon request. Plan the perfect trip to Lake Como with our guide.
Trentino
Vie ferrate
Scenic high-altitude trails crisscross the Dolomites, many equipped with vie ferrate – mountain routes with rungs, ladders and steel cables that cling to steep rock faces, making for an exhilarating way to take in the mountain panoramas. Two to seven-day experiences in the dramatic Pale di San Martino massif take hikers along scenic trails through the Parco Naturale Paneveggio, crossing several vie ferrate and overnighting in traditional mountain huts.
Ferrata packages with Palaronda Trek cost from ￡156pp for two nights on a half-board basis. Flights not included.
Umbria
Sweet highs
The Umbria Jazz Festival yearly pulls in quite a crowd, with an exciting line-up of artists playing in the regional capital, Perugia (Lenny Kravitz is set to open this year’s festival). Jazz aside, Perugia is renowned for its exquisite chocolate, celebrated yearly during the Eurochocolate Festival, which this year marks its 30th edition. And if you’re seeking a way to burn off your energy, you can do so by walking Sellano’s new Ponte Tibetano, which stretches half a kilometre over the Vigi River valley at a record height of 175m – it’s said to be Europe’s highest suspension bridge.
The 10th-century Hotel Castello di Reschio northwest of Perugia offers rooms from ￡787, B&B.
Aeolian Islands
Making waves
The ruggedly beautiful volcanic Aeolian Islands can get exceptionally busy in summer, with prices hitting a peak in July and August. Experience all the beauty of the archipelago away from the crowds aboard a classic wooden windjammer sailing boat, with daily trips ashore to explore the islands. There are plenty of opportunities to swim and snorkel in secluded coves, and there are SUPs and kayaks for guests, too.
The eight-day Aeolian Islands sailing trip aboard Florette with VentureSail is priced from ￡1,095 on a half-board basis, including six meals, full crew and tuition, all tender trips during the voyage to and from the boat, and equipment.
Piedmont
Gourmet delights
The vine-clad hills of Piedmont’s Langhe-Roero and Monferrato are real foodie territory, with outstanding restaurants and some of the world’s best wines produced in the area, including fine Barolos and Barbarescos. Complete with 1920s wooden carriages, the historical food and wine TrEno rolls through the landscape, with a new itinerary added this year to enhance the experience. As well as wine tasting on board, gourmands will enjoy a traditional lunch Acqui Terme, renowned for its Brachetto, a lightly sparkling, sweet red wine.
Stay at La Villa Hotel, a 15-minute drive east of Nizza Monferrato, where rates start at ￡225. The TrEno experience costs ￡140.
Venice
Lessons on the water
In April, Venice was the first city in the world to introduce an entry fee for day-trippers. Big cruise ships, meanwhile, were banned in 2021, although it’s still possible to experience Italy’s greatest city on water aboard a boutique river cruise boat (complete with House of Fortuny fabrics, original Murano glass chandeliers and objets d’art). A new activity has been added to this year’s programme to support local traditions, with Venetian rowing lessons aboard traditional batele run by Row Venice, a non-profit organisation of female rowers.
Uniworld’s eight-day Venice and the Jewels of the Veneto starts from ￡2,799pp. Plan the perfect trip to Venice with our guide.
South Tyrol
Ladin culture
Alta Badia and Val Gardena are home to the Ladin people, who settled here thousands of years ago and share age-old traditions, customs and a common language in Ladin, part of the Romance family. Visitors can learn about a handful of new ‘Nos Ladins’ experiences on offer in Alta Badia, including time spent with a local luthier at her workshop, learning about the art of violin making – the instruments are handcrafted using pine wood sourced from the surrounding forests.
First opened in 1932, Pralongia is the oldest and highest mountain hut on the Pralongià plateau, and re-opens this year for its first summer season following a complete refurbishment, with double rooms starting from ￡127pp per night, half board.
Valle d’Aosta
New heights
It may be Italy’s smallest region but the Valle d’Aosta has no shortage of awe-inspiring scenery (it’s home to Mont Blanc, after all). Last July saw the Matterhorn Alpine Crossing go into operation, connecting the ski resort of Cervinia with Switzerland’s Zermatt, offering views of the Matterhorn from the moment you step onto the cable car until you reach the summit. In summer, over 400 kilometres of hiking trails crisscross the mountain peaks, with marmots and chamois a common sight.
Macs Adventure offers the self-guided, six-day Tour of the Matterhorn South for experienced hikers, with two glacier crossings with experienced guides. Ending in Zermatt, the tour is priced from ￡1,190 and includes B&B accommodation in traditional mountain huts and hotels, four dinners, a qualified guide, route notes and maps. Flights not included.
Mount Etna
Mastering culinary skills
The volcanic soils of Sicily’s Mount Etna are known to produce excellent wines along with outstanding agricultural produce, including plump lemons, olives and pistachios. You can get a flavour for the region’s rich cuisine at Palazzo Previtera, a centre for contemporary art with rooms on the slopes of the peak, with foodie experiences including foraging for hazelnuts and wild herbs at a nearby farm, joining a local shepherd to learn about Sicilian cheese making, and hands-on Sicilian cooking classes in the Palazzo’s kitchen.
Palazzo Previtera offers rooms starting from ￡153 on a B&B basis. Foodie experience start from ￡30 per person.
The article was first published in April 2023 and has been revised and updated.
