How to plan a trip to Italy

written by Joanne Owen

updated 26.07.2023

​Radiating vitality from its natty north to its stylish southern heel, there are plenty of reasons Italy attracts a remarkable range of traveller types. Given its fabulous food, sun-soaked coastline, picture-perfect panoramas, and all those extraordinary ancient sites, it’s no wonder Italy sparks a desire to return. There’s simply too much to see — and fall in love with — during a single trip, and planning a stay in Italy can be overwhelming.

That’s why we’ve created this guide to planning a trip to Italy - to help you make the most of your time in this perennial stunner. These simple steps will help you decide where and when to go, and where to stay. Crucially, we’ll also show you how you’ll stay connected while you’re away.

This article is inspired by our Rough Guide to Italy — your essential guide for travelling in Italy.

1. Decide where to go in Italy

Let’s start with the obvious. After honing in on what you most want to see and do during your trip to Italy, you’ll need to decide which destination(s) you’ll visit.

Maybe you’ve always wanted to explore world-celebrated ancient sites. In which case, say ciao to Roma, Pompeii and Herculaneum!

Alternatively, if you fancy indulging your appetite for la dolce vita (and we mean literally), head to the Amalfi coast for limoncello, gelato and seafood, Naples for pizza and buffalo mozzarella, and Tuscany for wine.

If, on the other hand, you’re looking to absorb awe-inspiring art, make your merry way to Florence or Venice.

Want to be charmed by lesser-visited villages and towns? Exploring Emilia Romagna — Tuscany without the-crowds — might be your glass of Romagna Albana (that’s one of the region’s star wines).

The good news is, many places in Italy offer a mix of ancient wonders, glorious grub, fine wine, and undeniably breath-taking vistas, which means you might not have to choose one over the other.

Still undecided? Dive into our gallery of the most beautiful places in Italy.

Riomaggiore of Cinque Terre, Italy © Shutterstock

Riomaggiore of Cinque Terre, Italy © Shutterstock

2. …or take a multi-destination trip

If you have the time and budget to visit Italy for longer (lucky you), you could look to plan a trip that takes in a few destinations.

Independent travellers will be delighted to discover that getting around Italy is pretty easy. Travelling by train is a veritable breeze, and beautiful with it. The Italian system is pretty efficient and remains one of Europe’s least expensive rail networks.

That said, be wary of trying to cover much. With a nod to the fact that Rome wasn’t built in a day, don’t try to see everything in a single trip.

What’s more, you’d also be wise to factor in time to seize the day and enjoy spontaneous experiences — more on that later.

3. Decide when to go

Choosing when to go to Italy will, of course, depend on what you want to do, and your budget.

As a general rule, it’s worth bearing in mind that August in Italy can be blisteringly hot. In addition, coastal areas, resorts, and historic cities like Rome, Venice and Florence will be packed, and much pricier.

If you’re not a fan of sweaty crowds and huge queues, better to visit between April and June, or in September and October.

Aerial view of famous medieval San Gimignano hill town with its skyline of medieval towers © Shutterstock

Aerial view Italy's famous medieval San Gimignano hill town © Shutterstock

4. Pre-book accommodation and tickets for attractions

Whichever you decide to go for — a multi-destination trip, or a single location break — it’s always a good idea to book transport, accommodation and tickets for top attractions in advance.

That’s especially important in high season, when demand for accommodation and flights are at a premium, and at premium prices.

It’s also worth pre-booking tickets for Italy’s major tourist attractions at any time of the year. For example, when it comes to the likes of Florence’s Uffizi and Rome’s Coliseum, folks without pre-booked, skip-the-line tickets can expect to queue for a couple of hours, even out of season.

In short, booking ahead will save you money, save you stress and save you time. Crucially, it will also save you from kicking yourself for missing out on special experiences.

5. Be prepared – pre-arrange data connection

Once you’ve sorted how you’re getting there and where you’ll stay, don’t forget another crucial part of planning your trip to Italy. Namely, figuring out how you’ll stay connected while you’re away — without hassle, and without breaking the bank.

Even if you’ve sworn off checking work emails during your trip (good for you), having access to affordable data will always enhance your trip.

For a start, it will make finding your way around much easier, and enable you to stay in touch with folks back home. Chances are, you’ll also want to post as-they-happen images of your trip. In order to do that, you’ll need instant access to data.

In all likelihood, you’re already very well aware of these benefits, but might have reservations about the cost — no-one wants to pay over the odds to stay connected while they’re away. Happily, if you get yourself an international SIM card or eSIM from SIMCorner, a trusted Rough Guides’ partner, you don’t have to.

Thanks to partnerships with leading telecom providers around the globe, SIMCorner has products to suit every traveller - and they’re perfect for those planning a trip to Italy.

In good news for those of us who are weary of hidden costs and don’t want to be tied to long-term commitments, SIMCorner’s generous data allowances and services are contract-free. This means you can use your SIM card or eSIM when you need it, and pause it when you don't. Simple.

View over the famous Village of Limone sul Garda, Italy © Shutterstock

View over the famous Village of Limone sul Garda, Italy © Shutterstock

6. Leave time to seize the day

Fittingly, the carpe diem (seize the day) maxim was coined by Roman poet Horace over 2000 years ago, and heeding his wise advice might just enhance your experience of his homeland.

As for what that means in practice, try to factor some flexibility into your schedule when planning your trip to Italy. That is to say, leave time to be spontaneous so you can enjoy unexpected experiences - and Italy promises plenty of those!

You might, for instance, hear about a pop-up event, gig or exhibition from fellow travellers or local residents. In addition, once you’re in situ, you may well find yourself wanting to pursue new-found passions for Italian culture.

We’re talking food-themed tours and cooking classes, getting the low-down on local traditions at a vineyard and soaking up contemporary culture on a street art tour.

On a practical note, being able to seize the day is all the easier if you have instant access to affordable connectivity that allows you to look up current events and arrange impromptu local tours.

Of course, connectivity also comes in handy when you want to share evidence of your envy-inducing experiences on your social platforms of choice.

In short, allow time to say yes to last minute invitations, and indulge the new-found amore that Italy is sure to inspire.

Cathedral of Saint Mary of the Flower in Florence © Shutterstock

Cathedral of Saint Mary of the Flower in Florence © Shutterstock

Take a trip designed by local travel experts

Our local experts can plan wonderful trips for you in Italy. Simply get in touch when you would like to travel. We will then create a personalized itinerary, which you can amend until you are totally happy with every detail of the booking. All of our planned itineraries can be tailored to meet your specific needs.

This article is brought to you in partnership with SIMCorner

We may earn commission when you click on links in this article, but this doesn’t influence our editorial standards. We only recommend services that we genuinely believe will enhance your travel experiences.

Joanne Owen

written by Joanne Owen

updated 26.07.2023

Joanne is a Pembrokeshire-born writer with a passion for the nature, cultures and histories of the Caribbean region, especially Dominica. Also passionate about inspiring a love of adventure in young people, she’s the author of several books for children and young adults, hosts international writing workshops, and has written articles on the Caribbean and inspirational community initiatives for Rough Guides. Follow her @JoanneOwen on Twitter and @joanneowenwrites on Instagram.

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