The best Italian winter destinations

Italy in winter is a masterpiece of elegance, with its snow-kissed mountains and historic cities that create an atmosphere of pure indulgence. Discerning travellers can imagine a dream Italian holiday spent gliding through chic boutiques, savouring gourmet truffle-rich cuisine, or retreating to the Alps for a ski vacation framed by five-star chalets for rent. Staying in Italy for the season invites tourists to slow down, linger over a glass of velvety red wine by a crackling fire in a private villa rental, and embrace the art of the la Dolce Vita lifestyle. A luxury villa stay allows guests to enjoy exquisite meals prepared in-house or catered, turning every dining experience into a celebration of Italian flavours, comfort, and style. As the temperature drops, the warmth of Italian hospitality becomes irresistible. From the romantic terraces of the Amalfi Coast to the unique beauty of the Tuscan landscapes, the charming retreats of Umbria, or the sunlit streets of Ortigia in Sicily, every detail transforms a simple vacation into something truly extraordinary.

Cozy moments in your private villa

Here are our top picks for winter destinations in Italy.

Italian Alps, skiing and alpine wellness
No introduction to Italy’s winter escapes feels complete without beginning in the Italian Alps. Draped in immaculate snow, the region offers exceptional skiing, elegant snowshoeing trails and sweeping alpine panoramas. Refined villages with timbered chalets and artisanal markets create the charm of a cinematic retreat during the colder months. After exhilarating hours on the slopes, guests can relax in sumptuous mountain chalets for rent in the Dolomites and enjoy the indoor pool and the exclusive wellness facilities of their private chalet rental. The Italian Alps present a rare balance of adventure and discreet seasonal sophistication.

Italian Alps

Siena and Val d’Orcia area, Tuscan slow luxury
Tuscany unfolds in a harmony of muted light and rolling hills while the Val d’Orcia’s iconic cypress avenues rest in tranquil stillness. Hilltop villages and traditional villas for rent in Tuscany invite unhurried exploration and reflective wanderings. Siena enchants with its medieval streets, grand piazzas and the quiet elegance of historic architecture. Local trattorias offer the warmth of Tuscan cuisine perfectly complemented by generous regional wines in a luxurious frost-kissed tasting experience. In the depths of the colder season, Tuscany reveals an intimate charm that feels effortlessly refined.

Siena, Tuscany

Amalfi coast, scenic wonders and winter lemons
The Amalfi Coast in winter reveals a quieter, more intimate side of its legendary beauty, where sun-dappled cliffs and colourful villages shimmer against the tranquil Tyrrhenian Sea. Positano’s cascading terraces, Amalfi’s historic cathedral, and Ravello’s hilltop gardens offer breathtaking vistas without the summer crowds, creating an atmosphere of refined elegance. Luxury villa rentals provide a private sanctuary to savour exquisite seafood, local pastries, and celebrated regional wines, all while gazing out over the sparkling coastline. In the cooler months, the coast’s mild climate and enchanting towns make it the ultimate Italian winter destination, a place where sophistication, natural beauty, and cultural richness blend seamlessly into an unforgettable escape.

Amalfi cathedral

Umbria, sparkling winter soul and quiet elegance
The season in Umbria is one of quiet enchantment, where mist-covered hills cradle medieval towns in an ethereal glow. Gubbio shines with its famed Christmas tree, bathing the town in festive radiance while Castelluccio di Norcia and Mount Subasio rest beneath pristine blankets of snow. Orvieto comes alive with the intimate ambience of Umbria Jazz Winter, filling storied piazzas and palaces with soulful melodies amid serene streets. Assisi adds a profound sense of spirituality, where sacred sites invite reflection and contemplation. Hilltop retreats and luxury villas for rent invite indulgence in hearty Umbrian dishes and expressive regional wines. In the colder months, Umbria becomes a graceful, romantic and spiritual sanctuary where culture, nature and tradition blend with distinctive elegance.

Charming medieval streets

Escape to Sicily's golden festive season
Sicily unveils a gentle radiance where sun-washed coastlines meet the calm Mediterranean horizon. Siracusa, with the charm of Ortigia, offers a glimpse into the island’s rich heritage. At the same time, the dramatic landscapes of Mount Etna, the ancient ruins of Selinunte, the baroque splendour of Noto, and the timeless Valley of the Temples in Agrigento showcase Sicily’s cultural wealth. Luxury villas for rent provide private havens to enjoy authentic Sicilian cuisine, regional wines, and cherished moments of togetherness with family or friends. As winter unfolds, Sicily transforms into an intimate and enchanting retreat, where history, gastronomy, and the unique spirit of the South create unforgettable experiences.

Noto, Sicily

Contact us to craft your last-minute winter getaway and wander through our curated selection of exquisite villas. Let our villa specialists guide you to the perfect retreat while our top-notch concierge service ensures every detail is flawlessly arranged. Experience effortless luxury and make your seasonal escape truly unforgettable