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Plan a Trip to Italy

Ciao! So, you’re planning a trip to Italy soon? Allora…On this page you’ll find everything you need to start planning your trip to this enigmatic and enchanting country. Everyone thinks they know Italy, but this spectacularly diverse country is so much more that its iconic cities and ancient sites. The country cannot be defined by one personality, but many. Search a little deeper, drive a little further, stay a little longer – you’ll be surprised just how different Italy can be than what you expected and just how much the really is to unearth.

Planning a trip to Italy? You’re in the right place! Welcome to Travel Planning and Itinerary design by Candy. Ciao! I’m an independent travel advisor living in Portugal (since 2016). I help people plan their dream trip to Portugal, Spain and Italy. You’re currently reading a post from my collection of travel guides. I also offer personal travel consultation and a bespoke itinerary service.

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Best Places to Visit in Sicily
Blue boat, clear water La Maddalena
Siena washing, Tuscany travel guide

I spend months each year exploring my favourite country – Italy (sshhh, don’t tell Portugal). Over the years I have been trusted to build itineraries for travellers all over the globe. I’ve built up extensive knowledge about this passionate country.

Italy Trip Planner

Think of me as your personal Italy trip planner. On this page I’ll guide you through the process of planning a trip to Italy and offer helpful tools, travel guides and resources too. Whether you are looking for reliable travel information & genuine suggestions to plan your own trip or you want to work with a travel planner who knows the country deeply, you’ll find it all on this website.

Procida, Corricella Marina

Travel & Photography by Candy : What you see is real. No images in any of my travel guides are AI. All photos in this travel guide are taken by me. I spend a huge amount of time photographing, editing and uploading all the photos on this website. Please do not reuse them without credit and a backlink to this page. Thank you.

Recent Italy Travel Guides

Regions of Italy

Italy’s big boot covers just over 302,000km2 (including the islands of Sicily and Sardinia) and can be split into 20 (yes, 20!) regions; each with it’s own culture and charm. If that’s not enough to show you just how many sides Italy has to its personality, I don’t know what is. The 20 regions of Italy are :

  • Abruzzo 
  • Aosta Valley 
  • Apulia 
  • Basilicata 
  • Calabria 
  • Campania 
  • Emilia-Romagna 
  • Friuli-Venezia Giulia 
  • Lazio 
  • Liguria 
  • Lombardy 
  • Marche 
  • Molise 
  • Piedmont 
  • Sardinia 
  • Sicily 
  • Tuscany 
  • Trentino-South Tyrol 
  • Umbria 
  • Veneto 

While I don’t recommend generalising Italian regions, for ease of planning and logistics, you can also split the country of Italy into 4 areas :

  • Northern Italy
  • Central Italy
  • Southern Italy
  • Islands (Sicily & Sardinia)
Man on bike, BarI, Apulia, South Italy
Amalfi beaches in winter, southern Italy travel guide
Pizza, Naples, best places to visit Southern Italy

Tips for planning a trip to Italy

  • Let go of the idea of “doing it all”.
  • Choose one region to explore at a time will give you a deeper experience.
  • Forget the overarching generalisations of Italy; the country differs drastically from north to south which is part of its beauty.
  • Eat everything but don’t just stick to the pizza and pasta. Italy has so many regional delicacies to indulge in like Tartufo di Pizzo (truffle chocolate ice-cream bomb) in Calabria and Stigghiola (intestines)in Sicily.
  • A road trip is great way to link together multiple regions, especially in the south.
  • Scooter trips are a fun way to explore but choose your location carefully and avoid very busy cities like Naples.
  • Do go off-grid ( a few streets back) when looking for restaurants. Don’t rely solely on Google reviews.
  • Learn some language. English is widely spoken in the main cities but less so in rural and lesser-known areas. Hand signals and a few words will help. Language is a huge part of culture and we should do our part to respect that. Even in places where english is spoken, a few words and phrases will be appreciated. Start with a friendly ‘buongiorno!’(good morning).

When to Visit Italy

This depends on many factors. Mainly – which part of Italy do you wan to visit and for what reason? Shoulder seasons May/June and September/October are universally good for comfortable weather wherever you are and avoiding the main rush of summer. The main cities like Rome, Florence, Venice, Palermo, Naples etc can be visited at any time as they never shut down. They are busiest during the mid-summer months. If you’re looking for snow, the Dolomites are best visited in Jan-March. If you’re looking for a beach getaway June onwards in the south pretty much guarantees sunshine until November. Archipelagos such as the Aeolians all but shut down in the mid-winter months. For road trips those shoulder months are best but if you don’t mind less options the winter can be rewarding for driving. If you’re in the north, winter tyres and snow chains are mandatory during winter.

The climate varies greatly from tip to toe as do the crowds and activities available.

Travel Guides for Italy

Sicily Travel Map

Sicily Trip Planning Map

Looking for the best places to visit in Sicily all in one place? The Sicily Travel Map has more than 150 pins to help you plan a meaningful trip. I created this map to inspire your itinerary and make planning easier. The map includes a food guide, authentic restaurants, trattorias and osterias, the best spots for aperitivo, road trip ideas, cities, islands, remote beaches, hiking trails and areas of natural beauty. Local activities and genuine experiences. Everything you need, for the cost of one pizza. Mamma Mia!

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Human Travel Planning. No AI here.

What you see & read here is REAL. I don’t use ChatGP or other AI to write my travel guides or design itineraries. Travel is a human experience that requires all of the senses. It is impossible for AI to replicate that. Working with a human travel planner means working with someone who understands that travel is a highly unique and personal experience, not a ‘copy and paste’ job. All travel guides have been written by me from my own personal experiences. All the photos on this website are taken myself during my own travel. Nothing has been created using AI so you can trust what you are seeing actually exists.

Candy 35 Parallelo, Lampedusa island
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