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Top 10 Italian holiday destinations to visit for an adventure

Italian holiday destinations can provide you with the opportunity to surround yourself with rich history, culture and character in every corner of the country. You can relax on beautiful beaches, capture incredible cityscapes on camera, walk within the wine region or discover the land of the motors!

Whatever you wish your Italian adventure to look like – if travelling with a companion or by yourself – read on for a little inspiration and information. Sure to get you longing for a Latin adventure!

First, let’s pick one of these top 10 Italian holiday destinations to visit. Did you know that Rome is older than Italy itself? It’s a top destination for a European city escape…

Italian holiday destinations for a city break


Go back in time during a city break in Rome. You don’t need us to tell you about the abundance of ancient Roman décor and architecture you can enjoy while sightseeing. There are many archaeological sites, such as the Colosseum and Pantheon to explore. Make sure you also have your change ready to make a wish at the Trevi Fountain.  Enjoy photography? Capture views of the city at dusk from the top of the Spanish Steps. Before leaving, don’t forget to taste what Italy is famous for –  authentic stone-baked pizza and gelato ice cream.

eat pizza in Rome



Milan holidays offer the opportunity to embrace a cosmopolitan lifestyle while appreciating Italian culture and tradition. To gather your thoughts first, visit Milan’s unique, Gothic cathedral. Then stroll around stylish stores such as Prada or shop within independent boutiques for clothing and furnishings. Want inspiration for an outfit? Hit pause and people watch while dining at a superlative restaurant in Centro Storico (the historical centre). Here, a blend of old and new cuisine, from pizza to magical, molecular meals can be tasted.

an Italian holiday in Milan

While you are in Milan, head just to the North to visit Lake Como, an idyllic Italian holiday destination for a villa holiday within the Alps.


Back towards Rome you will find the carefree city of Florence. We recommend spending time here to take in all of Florence’s hidden beauty. It’s also worth visiting if you’re a fan of the arts. Found on the banks of the River Arno – Florence holidays provide a serene setting for sunset walks and picnics. Full of colourful renaissance architecture, the Uffizi Gallery, and luxury boutiques, Florence may be small but has lots to offer. Despite its cultural reputation there is great shopping to be found just across the medieval Ponte Vecchio Bridge. From Florence, you can take the train a short distance to visit Michelangelo’s birthplace – Caprese Michelangelo – a small village within rolling hills, situated in the High Tiber Valley. The perfect place to begin a walking holiday in Italy



Italian Holiday destinations for Walking


Tuscany is a region in central Italy, with an idyllic, rolling landscape full of cypress and olive trees. With plentiful vineyards, it is naturally home to one of Italy’s most famous exports – wine. Taste it for yourself during a wine tour, or follow a wine trail within the wine region of Chianti. The trail runs between Florence to Siena. Stop on route at pretty villages and towns like San Gimignano (known as the city of beautiful towers) for lunch or wine tasting. Have lunch with locals and learn more about Italian culture. From here, you can travel south to relax on an award-winning sandy beach.

Tuscany Italian wine tour


For dramatic coastal scenery and a hint of luxury, visit Sorrento, situated in Italy’s ‘Neapolitan Riviera‘. Stay in a pink or yellow townhouse, with views of Mount Vesuvius and Sorrento’s two marinas. Chiesa di Sant’Anna is one with plenty to experience, including shops, bars, and a church. For a day trip via ferry, visit the charming island of Capri, to ride the Monte Solaro chairlift and view the whole of the island. For a self-guided walking holiday over one week hike along the Siren coast from Amalfi to Sorrento.  In the sun and heat get too intense during the middle of the day, you can always dip into the Mediterranean Sea to cool off.

Another Italian holiday location to discover beautiful beaches is Sardina…

Italian walking holidays


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Italian Holidays for the best beachside break


An Italian beach holiday on the island of Sardinia could be for you if you’re missing the sound of the sea and the feeling of warm sand between your toes. Try a setting like Porto Istana. However, if you want a little more from your Italian holiday than time on the dunes, Sardinia can assist. Take a break from the sun at the National Archaeological Museum of Cagliari to study artifacts, tour the towers and medieval city walls in Cagliari Quartiere Castello, or take up a water sport at Santa Teresa Gallura’s city beach. Divers will be delighted to discover the marine life in the Protected Marine Area of Capo Caccia.

Italian holiday by the sea


A picturesque paradise, Naples is the place to spend your time capturing panorama photos, of the Tyrrhenian Sea and its trio of islands Capri, Ischia, and Procida. This ‘bay with a view’ is also the gateway to the only active volcano in Europe – Mount Vesuvius. Just as old as the volcano are the inhabitants. A city whose streets were carved out over 4000 years ago, there are many alleyways and courtyards to wander along. Go in search of the best seafood platter and try an Italian pastry called sfogliatella.

Naples and mount Vesuvius


Romantic Italian Holiday destinations


For a romantic Italian holiday, Venice is the most obvious choice. Described as one of the world’s most mysterious cities, Venice covers 100 small islands within a vast lagoon. Why not take an escorted tour to Venice to learn about Venetian history inside the Doge’s Palace, explore cobbled streets, and sample inventive and popular traditional cuisine. You can book a tour via river cruise, land, or even by boarding the luxurious Venice Simplon-Orient-Express. Love travelling by train? View our great train holiday blog for more ideas…



Another hideaway for a romantic escape is Sicily, the largest island within the Mediterranean Sea. Not just a distinguished seaside destination but a home of many historic sites and both Greek and Roman ruins. Great examples can be seen in Syracuse. Not seen a live volcano before? Mount Etna is one to visit to see its incredible cones and craters that vent steam. Also, you should add the ancient city of Palermo to your Italian holiday itinerary. It’s where you can visit extraordinary chapels, a grand cathedral as well as the Palace of the Normans – a fine example of Arab-Norman architecture. Also, known for its historical architecture is Bologna…



Bologna – an Italian holiday destination for petrol heads

Bologna is the home of fresh pasta! A city that’s retained most of its authenticity through medieval and 16th-century architecture. However, it’s not just a historical Italian city with buzzing markets. Its well-known title is ‘the land of the motors’. Bologna holds this name, due to the number of motor companies and manufacturers that were established in the surrounding area, such as Maserati. To plan the perfect Italian holiday for petrol heads take the motor valley tour. It includes visits to the Museum Ferruccio Lamborghini in Funo, as well as the venue for the most important motor races in Italy.

a fast car


Travel insurance for an Italian Holiday

Have we given you enough destinations in Italy to plot and plan an Italian adventure? Maybe you’ll visit one destination, take the opportunity to venture to more, or go last minute! Either way, discover Italy’s true culture and character with confidence with Free Spirit Travel Insurance. With Coronavirus Cover included with all policies – from single to multiple trips throughout the year – we’re happy to give you the freedom to travel when you’re ready to do so.

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