Three Monkeys Online

A Curious, Alternative Magazine

23 of the best places to vacation in Italy

From the TMO Italy Travel Guide

Where to go for the best Italian vacation? That’s an almost impossible question to answer, given that Italy is one of the most popular tourist destinations in the world (see some of the statistics from ISTAT, the Italian statistics office).

We’re up to the challenge, though, but with a small caveat. Instead of giving you the best vacation places in Italy, we’ll give you some of the best places to vacation in Italy – 23 to be exact (why 23? Why not!) . Our method is simple – we’ve chosen popular destinations alongside some of our own favourites. We take into special account where Italians themseleves like to vacation, and we’ve listed some of the pros and cons of each destination.

We’ve also tried to take into account different types of holidays when compiling our best places to vacation list. Italy has a huge range of different destinations, suitable for every type of holiday. Often one destination can pool together art, culture, food and gastronomy alongside sporting activities. There’s something for everyone! We’ve included cities, national parks, and specific areas in order to give you a wide range of options.

So, without further ado, here’s our top 23 best places to vacation in Italy:


Perugia - capital of the Umbria Region
Let’s kick off the list with a beautiful and often overlooked city in central Italy. Perugia is the regional capital of Umbria, the region between Lazio and Tuscany. It’s a vibrant hill-top town, founded by the Etruscans, with an important University and a world-famous Jazz festival(held each year in July, with a series of free and ticketed concerts by international acts). It has great food, including the famous Perugina chocolate factory!

Key reasons to visit Perugia: Central location makes it easy to visit other cities like Assisi, Arezzo, Florence, and Rome. Small size makes it easy to explore, and the Umbrian countryside that surrounds it is beautiful.

Disadvantages It really is a hill-top town, making accessibility an issue, though there is a massive escalator which brings you to the top of the town.


Matera, a provincial capital in the region of Basilicata is one of the oldest continuously inhabited areas in the world, with sites around the city dating back to the paleolithic period. Matera is a city like no-other, with the historic Sassi di Matera or stones of Matera, caves sculpted out of the rock. For much of its history the Sassi were considered a sign of the poverty of the city, with people living in caves that were certainly unfit for habitation. In more recent years though, these caves have been re-visited through the lens of tourism, and you can now find hotels and bars here too. The city and its harsh stones have inspired many, in particular film-makers with films like Mel Gibson’s The Passion of the Christ and Passolini’s The Gospel According to St Matthew. Amongst the Sassi are a wonderful collection of churches, which helped in the decision to declare the Sassi and Rupestrian Churches of Matera as a UNESCO World Heritage Site.

Advantages of Matera for a vacation: Matera’s tourist industry is growing,
but it’s still a relatively uncrowded spot, and the scenery is breathtaking.

Disadvantages Getting there. The nearest airport is in Bari, in neighbouring Puglia.


All roads lead to Rome, caput mundi, they used to say, and no trip to Italy is complete without a visit to Rome. Italians themselves flock to the city, despite it’s national reputation for corruption and chaos. The truth is that Rome is a great-value city to visit, easy enough to travel around, and offers an unchallenged wealth of artistic and historical attractions all within a relatively small area. It’s got great food, hotels and loads of events. Rome is one of the world’s favourite destinations, and there are many, many good reasons for this.

Best type of Holiday in Rome: Probably a combination of weekend or short, week-long vacation – so you have time to visit many of the sites, and sample the atmosphere, without getting fatigued. You simply won’t be able to see everything first time around, so plan to return.

Disadvantages: The city is loud and chaotic. That’s part of its charm, but not to everyone’s liking. During the heat of the summer, with tourist crowds, that can be a problem.


Napoli - one of our 23 Best Italian Vacation Spots

In the 18th Century the Grand Tour writers like Goethe would declare ‘See Naples and Die’. It was one of the richest and biggest cities in Europe under the reign of the Bourbons.
Since the Unification of Italy the city’s fortunes have slid somewhat, and for years it has become almost synonymous with organsied crime and micro-criminality.

Why on earth would you include it in your best vacation spots then? Well, because, like many other cities once plagued with a poor reputation (Marseilles and New York spring to mind), Naples is re-inventing itself, and tourists are rediscovering the huge amount of things it has to offer. Architecture and attractions aside, Naples’ food and culture are the beating heart of Southern Italy. The city, rightly, prides its contribution to Italian culture: its musicians and writers are amongst the most important in Italy. Authors like Elena Ferrante and Erri di Luca have used the city as a cornerstone in their writing. And the backdrop of Vesuvius against the bay of Naples is still, as it was in the 18th Century, a sight to take the breath away.

Advantages: Easy to reach, and a great base for discovering Pompeii, the magnificent Reggia di Caserta, Ischia, as well as the cities own attractions.

Disadvantages: It’s a huge city by Italian standards, with all that entails, and driving here can be a particularly stressful experience!

Continue on to the next page for more of our 23 Best Italian Vacation spots