Luxury Holidays & Villa Vacations In Italy - 2026/2027

Winter in Italy

Winter in Italy (November – February) is a season of cultural discovery, festive traditions, delicious food, and mountain adventures. With fewer visitors in many historic cities, this is a particularly rewarding time to explore Rome, Florence, and Venice. You’ll be able to enjoy the country’s best museums, galleries and historic sites at their very quietest, as well as taking advantage of world-class shopping. Northern Italy experiences cooler temperatures, typically around 2C to 10C (36F – 50F), while the south remains milder and drier. Temperatures here range from 8C to 16C (46F – 61F), though it can sometimes feel even warmer in Sicily. December brings atmospheric Christmas markets, beautifully decorated streets, and elaborate nativity scenes. If you’re drawn to the mountains, the Dolomites deliver fabulous skiing with a distinctively Italian flavour.

Where are the best places to visit in Italy?

The diversity of Italy is enormous, ranging from ancient cities, vineyard-covered hills, mountain lakes, and volcanic islands. Our knowledgeable specialists will help you narrow down the best places to visit in Italy for a luxury vacation, but these are some of the highlights:

• Rome – Italy’s capital rightly sits on the podium of the world’s great cities. Legendary sites such as the Colosseum, the Roman Forum, the Pantheon and the Vatican are reason alone to visit, but such is the wealth of cultural treasures here that you can return again and again and still find plenty to do. Just as enjoyable as visiting Rome’s exceptional museums, galleries, and historical sites is allowing time to simply stop and absorb the beauty all around you. The marble columns standing beside café terraces. The Baroque fountains. The narrow streets that open suddenly onto piazzas alive with trattorias, ochre façades, and the living history all around you.
• Venice – As popular as Rome but with a different character entirely, Italy’s ‘floating city’ possesses a theatrical beauty. Iconic vistas greet you at every turn, with palazzi reflected in blue-green water, arched bridges crossing narrow canals, and gondolas moving silently past weathered brick and marble. The water is ever-present. Misty mornings soften the lagoon, while the evening light makes the Grand Canal glow in shades of gold and rose. Beyond St Mark’s Square and the Doge’s Palace lie artisan workshops, island churches, glass workshops, and labyrinthine alleyways where you can sample delicious cichetti bites alongside your signature Spritz.
• Tuscany – For quintessential Italy at its very best, Tuscany is unmatched. In the countryside, scenes of rolling vineyards, cypress-lined lanes, and hilltop towns appear straight out of the pages of glossy magazines. Adventure is there for those who seek it, but just as important is slowing the pace with long lunches under the shade of olive trees, and wine tasting in Chianti’s acclaimed vineyards. Beyond rural Tuscany, a cultural treasure trove awaits. Renaissance Florence usually steals the crown, but there is plenty more besides. Siena’s Piazza del Campo always makes an impression, even outside the legendary Palio, while Lucca holds centuries of history and art within its fortified walls.
• Lake Como – Surrounded by wooded hills scattered with strikingly beautiful villages and grand villas, Lake Como always makes an impression. Italy’s third largest lake has long attracted writers, artists, and film-makers, drawn by its combination of captivating scenery, ornate gardens, and architectural grandeur. It remains one of Italy’s most glamorous corners. Bellagio, often referred to as the Pearl of Lake Como, sits in a luxuriant setting with enchanting views across the water. You can explore the lake in timeless style aboard a wooden Riva boat, pausing to admire celebrated spots such as Varenna, Menaggio, Cernobbio and Como. In the hills above the lake, luxury villas provide the utmost privacy.
• The Amalfi Coast – Rivalling Lake Como in the glamour stakes, the Amalfi Coast clings dramatically to the cliffs and is another preferred hideaway of the European A-List. Its popularity is no wonder. The coastline is unashamedly beautiful, with lemon groves, terraced gardens and pastel villages descending towards a glittering sea. Positano tumbles down the hillside in layers of colour, Ravello looks out from its high gardens, and Sorrento’s beach clubs extend out from its buzzing marina. Boats trace the coastline between sea caves and tiny coves. They also whisk visitors out to Capri for a further dose of Amalfi glitz.
• Sicily – Just a few miles offshore from Italy’s southernmost tip, the island of Sicily is a land of intensity, history, and great beauty. Greek temples look out to sea, Norman mosaics glitter in dark chapels, and the volcanic slopes of Mount Etna rise above vineyards and citrus groves. Palermo’s markets spill over with seafood, spices and street food, while the Baroque towns of Noto, Modica and Ragusa glow honey-gold in the sun.
• Sardinia – Edged by water of improbable clarity, Sardinia’s white-sand beaches and wind-sculpted islands feel at times closer to the tropics than the Mediterranean. Along the coast, polished resorts, discreet marinas, and empty coves sit within easy reach of diving sites and glorious venues for luxury yachts to drop anchor. Yet Sardinia’s character runs far deeper than its shoreline. Inland, Bronze Age nuraghi rise from the landscape, while mountain forests, citrus groves, wildflower meadows and pastoral villages reveal a fiercely individual culture marked by centuries of history and tradition.
• The Dolomites – In striking contrast to Italy’s cities and coastlines, the stunning limestone peaks of the Dolomites are one of the best places in the country for outdoor adventures. Surrounded by pristine meadows and clear alpine lakes, in summer the Dolomites offer fresh mountain air and exceptional hiking. In winter, they transform into one of Europe’s most picturesque and stylish ski destinations.

If you have already visited Italy and are returning for new discoveries - or are simply looking to explore beyond the big hitters – there are countless other fascinating places we can recommend. In the north, Umbria delivers peace in nature, replete with olive groves, wooded valleys and medieval hill towns. In the south, Puglia’s sun-bleached hill towns are scattered with distinctive trulli houses. Here, the Baroque city of Lecce bursts with cultural wealth, while the Adriatic and Ionian seas converge on Puglia’s long, luminous coastline. For further inspiration and assistance in planning a personalised Italy vacation, contact our knowledgeable specialists.