Italian holidays with Simpson's in Tuscany, Umbria & Chianti, Sorrento & the Amalfi coast, Sicily, Venice, Rome & Florence

Simpson Travel's team of Italy specialists have hand-picked the finest selection of villas, apartments and hotels in Italy’s most sought-after destinations.

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Information about Italy

Italy Property
Villa Verderama
Villa Verderama Find out more about ItalyTraditional 5 Bedroom Villa
Le Filigare
Le Filigare Find out more about ItalyRomantic Apartments
Hotel La Collegiata
Hotel La Collegiata Find out more about ItalyPrestigious 4* hotel

Your perfect holiday in Italy

Whether your are looking for the very best of luxury villas with private pool, family villas within walking distance of a glorious beach, hotels and villas overlooking the Mediterranean, luxury hotels and rural retreats in the heart of walking country, cookery lessons, spa hotels in Italy, or charming rustic Italian simplicity, we can find the perfect base from which to discover Italian culture, Italian cuisine and her abundant natural beauty. To ensure our Italy Specialists can help you find the right holiday for your needs, they have personally visited every villa, holiday cottage, apartment and hotel in our Italy portfolio. As well as helping you choose the accommodation best suited to you, our Italy specialists will be able to make suggestions for activities accessible from the location of your chosen holiday in Italy. The Simpson Difference

Tailor made holidays

Our flexibility allows you to tailor-make your holiday in Italy to your specific requirements, including accommodation-only holidays allowing you to make your own arrangements for travelling to Italy and multi-centre holidays so you can experiance more of this wonderful country. All our Italy specialists need is a brief and we'll create a bespoke itinerary that will be uniquely yours.

Italian Holiday Destinations – something for everyone

Simpson Travel has hand-picked some of the most exclusive villas, holiday cottages, hotels and apartments in Italy to bring you a comprehensive selection in the most desirable destinations. Italy has something for everyone. The quaint but chic fishing villages of the Amalfi Coast, the intoxicating landscape of Sicily and the remnants of so many different cultures; Tuscany and Umbria awash with great architecture amid gentle green hills, olive and fruit orchards, and the peerless treasures of Venice, Rome and Florence. In the Sicilian city of Ragusa the streets come to life with artists’ performances during October at the ‘Ibla Buskers’ festival. Whilst the people of Modica celebrate Easter Sunday with the ‘Madonna Vasa-Vasa’, a very old and traditional Easter procession. There is a wide variety of romantic retreats, relaxing beach-side hotels and villas, and elegant hideaways in cultural hotspots to choose from. 


The weather in Italy – when to go

There is no “right time” to visit Italy, and even in the colder months in Britain, the climate is relatively mild in Simpson’s Italian holiday destinations with plenty still to discover. Sicily has an exceptional dry and hot Mediterranean climate between April and October and is still relatively mild in the winter months. Sorrento and the Amalfi Coast are sun-kissed in the summer between April and October, and the temperature rarely dips below 50 degrees in the autumn and spring. Tuscany and Umbria share the same balmy summer and, when the crowds abate, Venice, Rome and Florence are perfect for Christmas gift shopping. 

Italian coast holidays

For those who enjoy a beach holiday in Italy, Simpson's selection of Italian holiday destinations offers a wide choice to suit every taste. As you would expect, the island of Sicily has a coastline of great beauty, with wild untamed shores in spectacular nature reserves, small coves and even a beach at the edge of a city in Cefalù, whilst the gorgeous rocky coves of Sorrento and the Amalfi Coast are sheer bliss where the taste of the sea is served up in the many fish restaurants at the water’s edge. Southern Tuscany has its “White Beaches” and whilst Umbria is land-locked, even here you can bathe from the shores of Lake Trasimeno. Luxury hotels with private beaches, Mediterranean villas ideal for romantic breaks or families with children and cosy coastal apartments – Simpson’s Italy specialists will be delighted to help you choose the holiday which is right for you.

Romantic breaks and holidays in Italy

Italy probably has more than its fair share of romantic destinations, and when these are combined with a passion for food and for life in general, there is no doubt that Italy is a winning choice for a romantic break or holiday. We have a selection of fabulous hotels and properties ideal for honeymooners or couples who want to get away from it all and relax.

Activity holidays in Italy

Walking in Italy offers much for the enthusiast and the gentle stroller alike. The coastal paths of Amalfi, exploring the slopes of slumbering volcanoes, the flora and fauna of nature reserves, the ancient sites in idyllic spots on Sicily and inland hikes between the hill towns of Tuscany and Umbria – there is a lot to see! Many hotels offer boat trips to the small islands off the Italian coast – Capri and the Egadi Islands to name but a few - and cycling on these islands and the mainland is a good way to really enjoy your surroundings. Cookery lessons are available in many of our Tuscan hotels, where you can get to grips with delicious regional recipes using fresh, local ingredients. There are a number of Italian hotels where wine buffs will find plenty of opportunities for tastings of local and prestigious Italian wines. At Simpson Travel we are happy to tailor your holiday in Italy to match your interests, and we can also help arrange guided tours, which we hope will enable our clients to discover more about the real Italy.

Off-the-Beaten-Track in Italy

Whilst the regions in Simpson’s Italy programme are familiar, there is still much undiscovered territory well off the beaten tourist trail. In Tuscany, the 15 tiny chapels in the woods of San Vivaldo and ancient, treasure-laden hill-towns; along the Amalfi Coast, Sant Agata del Golfo nestling above Sorrento far away from the hustle and bustle, and in Sicily, rich in antiquities, the site of Eraclea Minoa looks out across the white cliffs of Capo Bianco and a fragrant pine wood. 

Italian Cuisine

The key to Italian food is fabulous, fresh ingredients and simplicity. Each region has its own specialities, but sampling the range of cheeses, cured meats, fish and of course pasta and ice cream is an opportunity not to be missed. There are a choice of hotels in Tuscany where you can enjoy cookery lessons and try your hand at re-creating delicious local dishes and Italian classics, and many more which provide wine tastings.  Our Italy specialists will be happy to advise you.

The regions of Italy – with Simpson Travel


Sorrento

This is the land of the sirens, a taste of the real Italy. The town descends steeply to cliffs looking across the Bay of Naples to Ischia and Capri. It has an excellent climate, beautiful beaches and chic boutiques; a charming base from which to explore the Amalfi Coast and Pompeii. Simpson Travel have put together a tempting selection of glamorous and elegant Villas and hotels in Sorrento. Nearby Vico Equense sits in a richly fertile area and is known for its pizza a metro – pizza cut by the metre and, in the hills, Massa Lubrense is surrounded by vineyards, olive and lemon groves. 

Amalfi

Awash with winding alleys, pretty squares, seafood restaurants and boutiques, this famous resort has great beaches and a medieval architecture, including the Cloister of Paradise. Just along the coast, Conca dei Marini is a quaint, authentic fishing village amongst lemon groves with wonderful views and a tranquil atmosphere.

Positano

This little town has been a favourite with artists and writers since the 1950s. Tiers of pastel-coloured houses, winding steps and car-free lanes, a pretty bay and smart boutiques grace this romantic coastal resort. 

Ravello

Ravello is well-known for its gardens at Villa Cimbrone and the lovely Villa Rufolo, which inspired Wagner’s Parsifal and where in the summer, classical concerts outdoors are a feast for the eyes and ears. Ravello sits high up above the Mediterranean, elegant and tranquil.

Praiano

One of the lesser-known towns of the Amalfi Coast, Praiano is a pretty retreat with a little bay sheltered by high cliffs and well-situated between Positano and Amalfi. It is a taste of the Amalfi coast as it was in the 1950’s.  In August, a candlelight festival, the Luminaria, is held in honour of San Domenico.

Western Sicily

The wild, western portion of Sicily has a taste of Africa, left behind by Arab invaders, and the ancient remnants of Phoenician and Greek settlers. Examples can be found in the remarkable sites of Segesta and Selinunte. From Trapani there is easy access to the lovely Egadi Islands.

Palermo and Mondello

Palermo has belle époque villas, grand architecture and charm aplenty. Don’t miss the opulent spectacle of the Basilica of Monreale, the local markets, and Palermo’s Riviera, Mondello; once a little fishing village and now a bustling hideaway for Palermitani.

Cefalù

This old town has it all; a dramatic mountain backdrop, a sandy beach, and a mighty cathedral on the main square. Its central location along the north coast of the island makes Cefalù a good choice for those who want to explore east or westwards.

Agrigento and Enna

The south-western town of Agrigento is of course blessed with the wonderful Valley of the Temples, idyllically positioned on a picturesque stretch of the Sicilian coast. The pretty town of Enna is in the mountains, within reach of the coast and interesting inland towns including Nicosia and Piazza Armerina.

Taormina

Mount Etna presides over Taormina, and out to sea in the Aeolian islands, Stromboli and Vulcano emit sulphurous plumes into a clear blue sky. The views from Taormina’s Greek theatre are breathtaking and the town below has lively cafés and a furnicular to Taormina Mare.

Siracusa and the South East

A stepping stone to the Baroque towns of the South East – Noto and Ibla di Ragusa among them – Siracusa is within striking distance of the lovely beach at Fontane Blanche and of the Vendicari Nature Reserve. Siracusa has notable Greek and Roman sites to explore.

Southern Tuscany

Cortona is close to the Umbrian border, with views over the hills and plains of Tuscany and Umbria. A walled town, its slopes are graced with medieval buildings and narrow alleys. Here you will be able to see Fra Angelico’s Annunciation in the Museo Diocesano. Another fortified town of the region, Montepulciano,  sits atop a narrow limestone ridge, and there are many interesting buildings to see, including Palazzo Bucelli and the magnificent Duomo.  In Siena, don’t miss oval, where the Palio horse races are held in July and August.  In the countryside which surrounds it, the rich red earth produces some of Italy’s finest wines and the restaurants are a gastronome’s paradise. Simpson’s properties in the region will allow you to soak up the peace and tranquillity well away from the tourist trail.

Umbria

Umbria is less well-known than Tuscany, an intensely Italian region with art-filled towns, craggy forests and undulating green pastures. Assisi remains a quiet and pretty  country town, but one where you can gaze upon the frescoes of Giotto, and discover an olive grove among the chaotic pattern of rooftops. Umbria is land-locked, but you can bathe in Lake Trasimeno, a beautiful stretch of water edged with small towns and forgotten castles. Spoleto is dominated by  its 13th century fortress, and the long, arcaded bridge of Ponte delle Torri.  It has inspired many authors, including Goethe and Hesse.  

Chianti

The wine country of Chianti is full of lovely medieval hilltowns where you will stumble across great art and architecture which would not be out of place in Florence. San Gimignano is famed for its 14 lofty towers, and is a UNESCO World Heritage Site. Take time to taste wild boar salami and the local white wine, Vernaccia di San Gimignano. Volterra is a must; with six city gates, romantically castellated medieval ramparts, Roman baths and a Teatro Roman, it has a wonderful atmosphere. Thirty minutes’drive away is Montaione, with vistas of cypress and vines, and woodland. Here you can visit the 15 tiny chapels in the woods of San Vivaldo. It is possible to visit the house of the poet Boccaccio in Certaldo, approached by a winding, cypress-bordered road.

Venice

Unique and unchanging, Venice breaks have always been a popular option for romantics.  But alongside the gondolas, St Mark’s Square, the Grand Canal and the Bridge of Sighs, there are quiet squares and delightful corners which merit a longer stay.  Simpson’s Venice hotels have been hand-picked to offer something for everyone.

Rome

Energising, fascinating and bursting with treasures, a holiday in Rome is a truly Italian experience.  Momentous architecture and sculpture, great shopping and fabulous food make this a year-round city.  Beat the crowds and take a Rome break or holiday in the winter, early spring and late autumn. 

Florence

Refined, sensuous and surrounded by the Tuscan hills, Florence is a feast for the senses.  This pearl of the Renaissance is an art-lover’s paradise.  Don’t miss the magnificent striped marble Duomo, the Ponte Vecchio and of course, the Uffizi gallery. Its proximity to the Tuscan countryside makes Florence a perfect base for an unforgettable holiday. It also has a lively nightlife and wonderful shops and bars. 

Simpson Travel - The Road Less Travelled
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