In this section...

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. Wherever you go you’ll be welcomed with open arms: part of la famiglia from the moment you arrive.


  • "We book with Simpson Travel as we know what we will get – out of the ordinary in every way, great locations, fabulous hosts and kindred spirits."

    Martin Sims, Solatio Cottage, Tuscany 2018

  • "Villa Passione is an absolute gem of a villa with some of the best facilities and pool we have ever experienced on holiday. Its location for all the main sights and cities of Tuscany was perfect."

    The Carraretto Family, Villa Passione, Tuscany 2018

  • "Who could ask for more? Villa Donatella is beautiful, quiet and peaceful with fantastic views. Nooks and crannies to explore and an excellent pool."

    Hala F Soegaard, Villa Donatella, Umbria 2018

  • "Thank you for our holiday in beautiful Villa Flavia. We enjoyed every minute. Puglia is a gorgeous region and this villa is in the perfect location to explore the nearby towns, villages and countryside."

    The Law-Keens, Villa Flavia, Puglia 2018

  • "We had an extremely memorable stay in Casa dei Limoni in a place which felt special and off the tourist beat. We were very well looked after by the owner and her mother."

    Mr & Mrs R Simpson, Casa dei Limoni, Liguria 2018

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.


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.