Introduction to Italy

It’s said that Italy is everything all at once: the romance-seeker’s oil painting, the music-lover’s symphony and a feast of gourmet proportions. Certainly, when it comes to luxury holidays, this beautiful, historic country has 1,001 reasons why you should choose it as your place in the sun.

This is your invitation to enjoy that elusive dolce vita. From Chianti’s world-famous wines to Florence’s breathtaking art and architecture; Umbria’s unforgettable landscapes to Puglia's charming trulli houses and gleaming Baroque cities, our luxury Italian holidays give you the time and space to soak it all in.

So choose your favourite from our inspiring collection of luxury villas and boutique Simpson Hotels, and know that you’ll be welcomed with open arms: part of la famiglia from the moment you arrive.


  • “Looks great on the web site and the reality was even better. Quiet location with truly beautiful views, and everything about the property felt spacious and well cared for. The owners went the second mile to make us feel at home.”

    Judy Morris, La Casa dei Mandorli, Tuscany 2017

  • “We had a lovely holiday at La Madonnina in Tuscany. The host was superb and the accommodation was a lovely rural Tuscan experience. Very peaceful and relaxing.”

    Audrey Riddle, La Madonnina, Tuscany 2017

  • “Villa owner and family members very obliging and most keen to ensure we had everything we needed. They also wanted to know how they could improve the villa and its surroundings. We like that, an eagerness to raise the standards even higher.”

    Sue Curtis, Casa dei Limoni, Liguria 2017

  • "Mille Desideri is set in beautiful, tranquil surroundings. The meals we had there were some of the best we've ever eaten in Italy. Nicolas, Sara and Rosa could not have done more to look after us and they clearly love what they do!"

    Ruth Guy, Mille Desideri, Tuscany 2017

  • "Casetta Carina near Gaiole in Chianti was a little piece of paradise… The pool has a stunning location and was a highlight of the holiday."

    Mr & Mrs P Livingstone, Casetta Carina, Tuscany 2017

Regions in Italy

Italy creates holidays that indulge the senses in every way. Bathing in sunshine on pristine beaches, slipping into city café culture surrounded by ancient splendour or walking through miles of green hills, vineyards and valleys – the luxury of choice is yours.

And wherever you stay, you’ll find yourself immersed in Italy’s rich and abundant traditions and culture, weaving together spiritual and secular. From the art galleries to thermal spas, magnificent cathedrals to wineries, this is your invitation to delve beneath the surface and be a part of what makes Italy unforgettable.


From Life is Beautiful to Under the Tuscan Sun, Tuscany’s charms have proved infinitely worthy of the big screen, its undulating landscapes, old town squares and Renaissance grandeur the stuff of cinematic masterpieces. And yet, it’s also a place of simple pleasures – good food enjoyed leisurely with that famous Chianti red.


The former home of St Francis of Assisi, Umbria’s expanses of largely uninhabited countryside are threaded with walking trails and pilgrimage routes. A visit to the ‘green heart’ is also an invitation to discover a host of art and architectural treasures, including vibrant Perugia’s national gallery and Orvieto’s magnificent duomo.


‘The Floating City’ is a dream destination: romantic, historic and atmospheric in equal measures. Its famous canals carry you below ornate bridges; within wandering distance of elegant squares, museums, art galleries and churches, and between the kind of architectural extravagances that have inspired artists, poets and writers for centuries.


Otherwise known as the Italian Riviera, Liguria is a meeting of spectacular coastline and UNESCO World Heritage Sites: Genoa’s magnificent Old Town and the pastel hues of Cinque Terre’s cliff-side villages. And throughout the summer, festivals across the region bring out the unique flavour this dramatically beautiful destination.


There’s a different side of Italy to discover on a holiday in Puglia – the land of the trulli, ancient olive groves and historic towns that take you on a journey from Byzantine to Baroque. And then there are the countless beaches and beach clubs that capture the diversity of this absorbing destination: unspoilt, unpretentious and full of creative flair, where the generosity of the locals is matched by the excellence of its cuisine.