Fantastic food, wonderful wine, amazing architecture, luscious landscapes… Italy is a country that was made for indulging. With so many cities, each with their own personality, it’s hard to choose where to go on Italian city breaks. Maybe you want to experience the glamour and history of Rome, with its colossal Colosseum; shop until you drop in Milan; or take a gondola ride in Venice. Perhaps you’re after the culture of Pompei and Naples in the south; dreaming of mountainous landscapes of the north; or want to traverse the streets of beautiful and artistic Pisa, Florence and Siena and Tuscany. Whatever your fancy, you’ll have plenty of history, culture and art to explore, as well as numerous gastronomic delights to enjoy on any Italy city break.

Italy City Breaks Ideas

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Italy City Breaks Guide

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Italy Testimonials

30 reviews
4.7 / 5
"Emily really understood what mattered to us and created a trip that felt completely personalised and thoughtfully organised. We had time to relax in Naples after each excursion, our transport provider was friendly and always on time, and it was a pleasure to be looked after by a local, who added an authentic touch to the whole trip. Visiting Herculaneum and Pompeii was a particular highlight - our guide was truly exceptional, making the visits truly memorable with an excellent command of English and an impressive knowledge of world history as well as the sites themselves."
L - UK
Published on 23rd February 2026
"Our Concierge was brilliant and super helpful - we'd recommend travelling with Original Travel based on her help alone! The Concierge was a new thing for us as previous travel companies did not have this feature, and we thought this was invaluable. We particularly enjoyed the food tour in Ragusa, seeing Mount Etna, driving in Ortigia and the sunset in Marsala. It is the first time we have used Original Travel and we were very happy with the service."
M - UK
Published on 29th September 2025
"Emily really listened and understood what I was looking for, and developed a fantastic itinerary based on that. The personalised tour of Siena was a real highlight - I had asked if we could see some James Bond filming locations, and our guide took a lot of time to review the films and take us to the exact streets, balconies, doorways and squares seen in the films. We all loved it, especially our boys, who are James Bond enthusiasts."
G - UK
Published on 29th September 2025

Short and sweet, a city break in Italy perfectly captures the cultural highlights and finest food spots of your chosen destination. Whether you’re in search of history, art, literature, fashion or food, Italy really does have a city for everything. Rome, the historic centre of the ancient world, is home to iconic sites such as the Colosseum, the Vatican City and Saint Peter’s Square. A guided tour of Villa Medici will take you behind the scenes of one of the city’s finest villas and this sightseeing excursion can be elevated with priority passes to the Sistine Chapel and the Vatican Museums.


Sun worshippers can escape to the UNESCO World Heritage sites of Syracuse, Ragusa and Val di Noto for a coastal city break. Located off the ‘toe’ of Italy’s ‘boot’, these Sicilian cities boast Baroque architecture, a juxtaposition of sea and mountain landscapes, and classic Italian cuisine. If you’re having trouble choosing a single place to aim for, our Italy city breaks can contain more than one stop. Travel to the Holy Trinity of Italy – Venice, Florence and Rome – by train, to experience each city’s own distinctive personality and artistic style at a relaxed pace.


Florence and Venice are the perfect artistic duo. As the birthplace of the Renaissance, the royal villas of Florence are not to be missed, while roads have been replaced by canals in Venice, and a gondola will be your main method of transportation. These cities also excel in the art of gastronomy and a guided tour of the San Lorenzo Covered Market will take you through the variety of regional specialities (cheeses, meats, focaccia and olive oil, to mention a few), ending with a tasting of the Chianti Classico red wine, which is produced nearby. Whether you’re after a whistle-stop visit or a leisurely long weekend away, our Italy city breaks are tailor-made to suit your specifications and our local Concierges will be on hand to offer recommendations.

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