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Tailor-made holidays to Italy

Italy is one of Europe's most endlessly rewarding destinations. From the grandeur of Rome and the romance of Venice to the vineyard-covered hills of Tuscany and the sun-drenched shores of Sicily, every region offers its own distinctive character, flavours and traditions.

Our tailor-made Italy holidays are designed around your personal interests, whether you're seeking world-class culture, exceptional gastronomy, luxury beach escapes, scenic rail journeys or multi-centre adventures that showcase the country's remarkable diversity.

With first-hand expertise, carefully selected luxury accommodation and access to extraordinary experiences both on and off the beaten path, we'll craft a seamless journey that reveals the very best of Italy in style.

 


What to expect on an Italy holiday

Italy combines unparalleled history, artistic treasures and culinary excellence with some of Europe's most beautiful landscapes. Ancient ruins sit alongside Renaissance masterpieces, while vineyard-draped countryside gives way to dramatic coastlines, glittering lakes and picturesque islands.

Travel here is as much about experiences as destinations. Mornings might be spent exploring UNESCO-listed landmarks, afternoons enjoying long lunches overlooking vineyards or the sea, and evenings savouring regional cuisine in atmospheric piazzas.

Whether you're travelling for a romantic escape, family holiday, honeymoon or grand tour, Italy offers endless opportunities to embrace the country's famous way of life.

Special Italy Holiday Experiences

  • Explore the Amalfi Coast aboard a private boat
  • Arrive in Venice aboard the Venice Simplon-Orient-Express
  • Explore Pompeii and Herculaneum with a private guide
  • Sail through the Aeolian Islands on a traditional tall ship
  • Tour Northern Italy in a classic sports car
  • Search for truffles alongside local experts in Abruzzo
  • Enjoy exclusive after-hours access to iconic landmarks
  • Learn traditional recipes during a local-led cooking experience
  • Charter a private yacht along the coast of Sardinia
  • Experience wine tastings in Tuscany, Piedmont and Sicily
  • Discover hidden medieval villages with expert local guides


Why visit Italy?

Italy's appeal lies in its remarkable diversity. Few destinations offer such an extraordinary combination of culture, cuisine, scenery and luxury. One day you might be admiring Renaissance masterpieces in Florence; the next, relaxing beside Lake Como or cruising past the colourful villages of the Amalfi Coast.

  • Explore world-famous cities including Rome, Florence and Venice
  • Indulge in some of Europe's finest food and wine
  • Stay in historic palaces, luxury villas and boutique hotels
  • Discover more than 50 UNESCO World Heritage sites
  • Experience the glamour of Lake Como and the Italian Lakes
  • Relax on the beaches of Sicily, Sardinia and Puglia
  • Journey by luxury rail, private yacht or chauffeured car
  • Visit iconic landmarks with expert guides and exclusive access
  • Embrace the timeless pleasures of La Dolce Vita

"What makes Italy so special is its extraordinary variety. You can enjoy world-class art, exceptional food, spectacular scenery and beautiful hotels all within a single journey. Whether you're visiting for the first time or returning to discover somewhere new, Italy never disappoints."

Matthew Grubb, Italy Destination Specialist

Italy Destination Experts

Our specialists know Italy intimately, from the iconic highlights to lesser-known regions that offer authentic local experiences. Whether you're dreaming of a villa in Tuscany, a luxury coastal escape on the Amalfi Coast or a multi-centre journey between Italy's cultural treasures, we'll design an itinerary tailored entirely to you.

Italian food

Discover the delights of Italian food on a cookery course

The canals of Venice

Take a gondola through the canals of Venice

Lake Como, Italy

Discover grand villas and scenic beauty on the shores of Lake Como


Luxury accommodation in Italy

Italy offers some of Europe's most varied and distinctive luxury accommodation. Spoil yourself with a stay in old-world Venetian glamour at the iconic Hotel Cipriani or base yourself in a private Roman residence. Take time out in a traditional Tuscan farmhouse or restored fort, experience life in a converted Franciscan monastery or traditional Puglian masserie and immerse yourself in a restored alberghi diffusi in the Abruzzo. Indulge yourself with vintages available at your hilltop winery retreat or bask in the luxury and privacy on offer at your private lakefront Como villa or stunning coastal escape. Ask us too about travelling on the Venice Simplon-Orient-Express to experience the golden age of travel in serious style on a great rail journey across Europe.

Historic Palaces & Grand Hotels

Stay in landmark properties that blend heritage, elegance and world-class service.

Luxury Villas & Private Residences

Ideal for families and groups seeking privacy, flexibility and exclusive surroundings.

Boutique hotels

Characterful properties offering personalised service in Italy's most desirable destinations.

Coastal resorts & beach retreats

Enjoy exceptional dining, sea views and direct access to beautiful coastlines.

Wellness & spa escapes

Luxurious resorts dedicated to relaxation, wellbeing and rejuvenation, located in some of Italy's most beautiful and historic locations.

Unique travel experiences

From luxury train journeys to converted historic properties, Italy offers unforgettable stays that are destinations in their own right.

View all accommodation


When to go to Italy

From autumn harvests to snowy winter scenes and the sheer beauty of an alpine spring, Italy is a wonderful option at any time of the year. Of course, the most popular spots can get busy the height of summer, and you might have to book several months in advance, particularly regions such as the Amalfi Coast.

Ask us about how to explore the country in the shoulder seasons, travelling to the cities, countryside or coast in spring or autumn instead, when the weather's warm and there are fewer crowds. Indeed, the beaches of Sicily and Puglia are arguably at their best in June or September. Otherwise, look out for annual events such as the Venice Carnival in February or the Palio in Sienna in July and August and plan ahead to secure the best bases from which to experience these exceptional events.

Italy in spring (April to June)

  • Sightseeing and city breaks
  • Walking holidays
  • Wine-tasting experiences
  • Amalfi Coast and Lake Como escapes
  • Mild temperatures and fewer crowds

Summer (July to August)

  • Beach holidays
  • Coastal cruising
  • Island escapes
  • Outdoor dining and festivals
  • Long sunny days

Autumn (September to October)

  • Harvest season in Tuscany and Piedmont
  • Food and wine experiences
  • Warm weather across southern Italy
  • Excellent sightseeing conditions

Winter (November to March)

  • City breaks with fewer crowds
  • Venice Carnival
  • Festive escapes
  • Alpine skiing in northern Italy
  • Cultural and culinary experiences

Best places to visit in Italy

From iconic cities and rolling vineyard landscapes to glamorous lakes and sun-soaked coastlines, Italy's regions each offer their own distinctive character. Whether you're drawn by culture, cuisine, history or scenery, there is an Italian destination perfectly suited to your style of travel.

Tuscany

Synonymous with rolling hills, vineyard-covered landscapes and Renaissance splendour, Tuscany embodies the romance of rural Italy. Explore Florence's world-famous art collections, wander through medieval hill towns such as Siena and San Gimignano, and enjoy private wine tastings in Chianti's renowned estates. From luxury country retreats to historic villas, Tuscany offers an irresistible blend of culture, cuisine and natural beauty.

Explore Tuscany holidays

Puglia

Occupying Italy's sun-drenched heel, Puglia is celebrated for its whitewashed towns, olive groves and idyllic Adriatic coastline. Stay in beautifully restored masserie, discover the unique trulli houses of Alberobello and wander the charming streets of Ostuni and Lecce. With its relaxed pace of life, outstanding cuisine and growing collection of luxury boutique hotels, Puglia is one of Italy's most appealing emerging destinations.

Explore Puglia holidays

Amalfi Coast

One of Italy's most iconic destinations, the Amalfi Coast combines dramatic scenery with effortless glamour. Colourful villages cling to rugged cliffs above the Mediterranean, while winding coastal roads reveal breathtaking sea views at every turn. Explore Positano's chic boutiques, discover the historic charm of Amalfi and enjoy the refined atmosphere of Ravello, all while staying in some of Italy's most spectacular luxury hotels.

Explore Amalfi Coast holidays

Sicily

Rich in history, culture and natural beauty, Sicily offers a fascinating blend of influences shaped by centuries of Greek, Roman, Arab and Norman rule. Discover ancient temples and archaeological treasures, explore vibrant cities such as Palermo and Syracuse, and relax beside beautiful Mediterranean beaches. From Mount Etna's volcanic landscapes to exceptional food and wine, Sicily rewards travellers seeking authentic Italy with a distinctive character.

Explore Sicily holidays

Italian Lakes

The Italian Lakes combine spectacular alpine scenery with timeless elegance, making them one of Italy's most sophisticated holiday regions. Encompassing the glamorous shores of Lake Como, the tranquil beauty of Lake Maggiore and the charming waterfront towns of Lake Garda, the region is ideal for relaxation and exploration alike. Expect grand villas, historic palace hotels, private boat excursions, exquisite gardens and breathtaking mountain views, all paired with exceptional cuisine and a distinctly refined Italian atmosphere.

Explore Italian Lakes holidays

Venice

Built across a network of picturesque canals, Venice is one of the world's most enchanting cities. Admire Byzantine architecture in St Mark's Square, glide through hidden waterways by private gondola and stay in legendary hotels overlooking the Grand Canal. Away from the crowds, you'll discover artisan workshops, atmospheric bacari wine bars and a timeless elegance that has captivated travellers for centuries.

Explore Venice holidays

Rome

Italy's captivating capital is a living museum where ancient history and contemporary culture exist side by side. Wander through the Colosseum, Roman Forum and Pantheon, discover masterpieces within the Vatican Museums, and savour long lunches in elegant piazzas. Beyond the iconic landmarks, Rome delights with stylish boutique hotels, Michelin-starred restaurants and hidden neighbourhoods that reveal the city's authentic character.

Explore Rome holidays

Italy Holidays: Frequently asked questions

When is the best time to visit Italy?

Spring and autumn are generally considered the best times to visit, offering pleasant temperatures, fewer crowds and ideal conditions for sightseeing.

Which part of Italy is best for a luxury holiday?

Italy offers luxury experiences throughout the country, from Lake Como and Venice to Tuscany, the Amalfi Coast, Sicily and Sardinia.

How many days should I spend in Italy?

We recommend between seven and fourteen days for a multi-centre itinerary, although shorter city breaks and longer regional explorations work equally well.

Is Italy suitable for a luxury honeymoon?

Absolutely. Italy is one of Europe's most romantic destinations, offering beautiful hotels, exceptional cuisine, spectacular scenery and unforgettable experiences.

Can I combine several regions in one trip?

Yes. Many of our tailor-made holidays combine destinations such as Rome, Florence, Venice, Tuscany, Lake Como and the Amalfi Coast in a seamless itinerary.

Is Italy a good destination for food and wine lovers?

Italy is one of the world's premier culinary destinations, with each region offering distinctive food, wine and gastronomic traditions.

When is the best time for an Italian beach holiday?

June and September are particularly appealing, offering warm temperatures and quieter beaches than the peak summer months.

Can you arrange private experiences and exclusive access?

Yes. We can arrange everything from private guides and wine tastings to after-hours cultural visits, yacht charters and bespoke culinary experiences. Just ask our Italy experts.

Why book with The Luxury Holiday Company?

Whether you're dreaming of cruising the Amalfi Coast, staying in a Tuscan villa, exploring Rome's ancient wonders or relaxing beside Lake Como, we'll create a journey tailored entirely around your interests.

When you book with The Luxury Holiday Company, you can expect:

  • Tailor-made itineraries designed exclusively for you
  • Expert destination knowledge
  • Handpicked luxury accommodation
  • Exclusive experiences and insider access
  • Financial protection and complete peace of mind
  • Seamless planning from start to finish

Start Planning Your Tailor-Made Italy Holiday

From the vineyard-covered hills of Tuscany and the glamour of Lake Como to the sun-soaked shores of Sicily and the timeless allure of Rome, Italy offers endless possibilities for an unforgettable escape.

Speak to our Italy specialists today and let us create a tailor-made Italy holiday that perfectly matches your interests, pace and style of travel.


Suggested itineraries

Sorrento

Sorrento & the Amalfi Coast

8-day tailor-made holiday from £2,685 pp excl. flights

Based in Sorrento, this is the perfect introduction to Italy’s Amalfi Coast. Across one memorable week, you'll relax, dine in style and join expert guides to explore the region's storied highlights.

Taormina, Sicily

Best of Sicily

8-day tailor-made self-drive from £2,085 pp excl. flights

This luxury road trip takes in the best of Sicily's ancient cities, pristine coastline and vineyard-studded interior, linking together the likes of Palermo, Cefalù and Taormina.

Hotel Hassler Roma at the top of the famous Spanish Steps in Rome

Roman Holiday by Hassler Roma

4-day tailor-made holiday from £2,615 pp excl. flights

A Roman Holiday-inspired escape, combining a stay at the Hassler Roma with private tours of Rome’s highlights and Tivoli’s villas and gardens.

Otranto, Puglia

Best of Puglia & Matera

11-day tailor-made self-drive from £2,510 pp excl. flights

Combine the historic treasures of Matera with an in-depth exploration of Puglia’s urban and rural delights, including a visit to the trulli houses of Alberobello, a cheese tasting experience and a stay on the gorgeous Adriatic Coast.

L'Albereta

Luxurious Lombardy Escape at L'Albereta

5-day tailor-made holiday from £2,385 pp excl. flights

Experience an unparalleled escape in Franciacorta, where world-class spa indulgence, exquisite culinary delights and exclusive vineyard tours converge. Enhance your journey with captivating day trips to Bergamo, Brescia, and the serene shores of Lake Iseo.

Tuscany

Florence & the Tuscan countryside in luxury

8-day tailor-made self-drive holiday from £1,620 pp excl. flights

With luxury stays in a riverside hotel and historic country house, this curated itinerary showcases Florence and Tuscany at their very best.

View all itineraries


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