With a handpicked villa portfolio spanning Northern Italy to the Amalfi Coast, we can curate longer stay holidays for guests seeking to experience Italy with greater depth and at a considered pace. From Tuscany’s wild beaches to the canals of Venice, our Villa Specialists will help you find the perfect place to call home in Italy.
The possibilities of an extended trip in Italy are endless – and nowhere is more evident than in Tuscany, Umbria, Veneto and beyond. Two weeks or more allows travellers to truly switch off and slow down. Long-haul visitors to Europe often want to experience at least a couple of places at a time, with a reliable base to return to. Italy’s diverse landscapes offer a rich and varied experience, whether you’re a beach person or a city seeker with a soft spot for nature.
Our handpicked portfolio of luxury villas in Italy ranges from restored farmhouses to stately homes and sprawling countryside estates. Some of them are located moments from the glittering coastline of Amalfi, others are nestled in the depths of the Chianti countryside.
For those who prefer culture on their doorstep, we also offer exceptional properties within easy reach of historic cities such as Florence, Venice and Perugia. The benefits of an extended stay mean that you can hop from town to town, and from villa to villa with ease.
To whet your appetite, here below are a few exquisite villa duos for longer, multi-destination stays across Italy.
TABLE OF CONTENTS
The perfect villa duo for beach lovers and city seekers
Charming villages, lakeside views and idyllic countryside immersion
Ancient landscapes, wild beaches and the treasures of Florence
Tick off Florence’s treasures the pristine lakes of Lake Garda
Live Italy’s rich heritage close to two of the country’s art capitals
Venture off the beaten path in Umbria
The authentic Umbrian experience
Coast to coast along Italy’s sparkling shores
The perfect villa duo for beach lovers and city seekers
Start your holiday on the coast of Tuscany with a stay at Agrumeto Dell’Isola, a spectacular stone farmhouse perched on the unpopulated western coast of the Monte Argentario peninsula. Days here are spent lounging by the beach in the sun, completely immersed in nature. Then move on to experience the immersive pleasures of Fontegaia for a culture fix, a spectacular villa within close proximity to Florence and all its treasures.
Charming villages, lakeside views and idyllic countryside immersion
Ideal for small groups or families, Ca’ Corniolo Maggiore offers the idyllic Italian Lakes experience in a charming village setting. Once you’ve explored Piedmont’s superb wine and food scene and Lake Maggiore, a stay at Ca’ Dogaressa offers the idyllic countryside experience amidst Colli Euganei’s rolling hills. The surrounding countryside is dotted with family-owned wineries and some of the oldest thermal spa centres in Europe.
Ancient landscapes, wild beaches and the treasures of Florence
This villa duo takes you from the countryside to Tuscany’s wild, rugged beaches. Start with a stay at Il Sogno di Leonardo, which is nestled among the picturesque olive groves above Vinci and Tuscany’s ancient landscapes.
The villa’s prime location in Tuscany means that you are only an hour from the treasures of Florence, Pisa and Lucca by car. Then make your way to Sartomare, which is just a short drive from the wild beaches of Maremma, Monte Argentario and the high-end beach clubs of Versilia.
Tick off Florence’s treasures and the pristine lakes of Lake Garda
Begin your Tuscan adventure within close proximity to Florence with a stay at The Estate of Petroio, set within a 650-acre Chianti wine and olive oil estate, ideal for family reunions. Spend a week sipping wine from the estate, dining on local delicacies like mouthwatering Bistecca alla Fiorentina, and marvelling at masterpieces in the Uffizi.
For the second week, set your sights on Villa Sigurtà to live like royalty for a week. Lake Garda, a short 25-minute drive away, beckons you to discover its picturesque lakeside towns, including Sirmione, where you can charter a boat for the day or enjoy the therapeutic thermal spas. By night, the Arena di Verona welcomes you for a night of opera or ballet before returning to a turn down service from your personal butler.
Live Italy’s rich heritage close to two of the country’s art capitals
This villa duo is one of the best ways to tick off a few spectacular towns, cities and small villages in Italy, and live like nobility all at once. Start with Ca di Lista, a splendid 16th-century Venetian villa still owned by the same family who can trace their origins to the founding of Venice. Its prime location in the Colli Euganei hills near Padua and Venice gives you a superb blend of countryside-to-city immersion. The property has lived a few lives since its heyday, evolving from a hunting lodge built by Dario Variotari – a Renaissance architect – to an elegant country retreat set within an award-winning wine estate.
After a week in the north, Villa Tinaccio offers easy access to nearby Florence, San Gimignano, Siena and the wider Chianti region. This renaissance-style villa has been in the same family since the early 15th century, offering guests a rich cultural experience close to some of Italy’s finest museums.
Venture off the beaten path in Tuscany and Umbria
For those seeking a highly personalised escape in Tuscany, Pieve di Ponsano’s secluded location in the countryside is a good place to start. Here, time slows down and the days are shaped around the rhythms of the seasons and landscape.
Bespoke wellness experiences can be organised by the pool, including sunrise or sunset yoga and in-villa spa treatments. Beyond the villa, enjoy scenic horseback riding, guided hikes through the Berignone Nature Reserve, private wine tastings and wildlife-life spotting walks.
Then make your way to the lavish Villa Clara just 7km away from Umbria’s hilltop town of Orvieto for further pampering overlooking the golden city. Our local concierge can arrange day trips to Terni, Viterbo and Todi, while the in-villa staff take care of all the details.
The authentic Umbrian experience
Begin your journey near Orvieto in Umbria with a stay at Loliondo, a private villa immersed in a 30-hectare olive estate in the Monte Peglia UNESCO Biosphere Reserve. Days here unfold at a slower pace, with authentic Umbrian experiences right on your doorstep.
Then drive to I Ruderi for your next stop to experience what it’s like to stay on the edge of a charming Italian village. San Gemini is a lively medieval town in Umbria steeped in history, largely untroubled by mass tourism. Visit 13th-century churches and dine at local trattorias before retreating to your private villa.
Coast to coast along Italy’s sparkling shores
Planning a longer-stay holiday by the sea? Beach enthusiasts will find plenty to tempt them along Italy’s coastline. In Positano, the iconic cliffside town famous for its colourful houses and sweeping Amalfi Coast views, Fraloga offers a peaceful base above the water. Further north, Castello di Punta Ala — built in the mid-16th century by Cosimo I de’ Medici — overlooks the Tyrrhenian Sea and the glamorous coastal town of Punta Ala.
This villa duo offers a superb coast-to-coast experience, stretching from the Amalfi to Tuscany’s Maremma. Both villas sit within walking distance of the sea, yet each offers a distinct perspective on Italy’s coastline: Positano delivers the iconic glamour of the Amalfi Coast, while Punta Ala remains a cherished local secret, beloved by Italians in the know.
Contact our Villa Specialists
Whether you’re hoping to tick off Florence, Venice, the Tuscan coast, or all three, our handpicked portfolio of luxury villas caters to longer-stay holidays. From restored farmhouses in the Chianti countryside to cosy villa stays in authentic Tuscan villages, each villa in our portfolio is selected for its character, charm and comfort. Tell our Villa Specialists what your ultimate villa holiday in Italy looks like, and let them take care of the rest.