How to Plan a Trip to Italy

By | Senior Writer
Last Updated: April 29, 2020
How to Plan a Trip to Italy: Step by Step Guide • Winetraveler

Italy was one of the most visited countries in the world.

Then coronavirus hit.

One of the first countries outside of China to have a major coronavirus outbreak, Italy was also one of the first to completely shut down. But we know that it will open up and receive tourists eventually and when that happens, Italy will desperately need your tourism dollars. Here’s how to start planning a trip to Italy — you can even start daydreaming and researching from the comfort of home.

How to Plan a Trip to Italy: Step by Step Guide • Winetraveler
The eclectic nightlife of Venice.

Start With Ideas

Actually booking and paying for your trip may not be the best plan right now, but you can easily start thinking about where you want to go. From virtually touring the Vatican to deciding which wine region to visit based on your favorite Italian variety, start slowly organizing your dream trip in your head. Take note of those frequent flyer miles and start thinking about the best ways to arrive in Italy from your home city

When it comes to tours and activities, it’s best to wait to book, but you can start looking for ideas of what you’d like to do. Consider using local guides and tour agencies once you make it to Italy — these types of smaller businesses may need your help the most.

Book Cautiously

Proceed cautiously when actually booking or reserving travel. If you really want to lock in something now, plan to travel in late 2020 or even 2021. It’s important to choose airlines or fare where you can cancel and get a refund/voucher or have your airline miles redeposited.

When booking flights, book directly with the airline and avoid third-party online travel agencies (like Expedia or Orbitz) as it will be harder to cancel or make changes. For hotels, you can use OTAs, but make sure to book cancelable rates. For home rentals, carefully read the cancelation policy before reserving anything.

Winetraveler Tip: Most trip insurance cancelation policies don’t cover coronavirus unless you personally become ill. If you do decide to get trip insurance, make sure to get the “cancel for any reason” coverage and carefully read the fine print.

Ideal Itineraries / Don’t Overplan

Italy is best savored slowly — just as its famed wine and cuisine. You wouldn’t be in a rush to down your cacio e pepe pasta dish or chug your Nero d’Avola, so you shouldn’t rush around trying to visit as many spots as possible. Depending on the length of your trip, most visitors coming to Italy for a week or two should plan to explore two regions/areas to best maximize time. Of course, within those regions, you can always explore more. For example, here are some popular itineraries that might be a good fit:

Rome and Florence: Yes, it’s one of the most obvious itineraries, but you can easily take the train between the regions; this would be a great beginner trip for first-time Italy travelers as both areas are used to an influx of tourists. Stops in Siena and the Tuscan wine country are a must.

Milan and Cinque Terre: Train down from Milan to see the picturesque cliffside villages of Vernazza, Monterosso al Mare, Manarola, Corniglia and Riomaggiore.

Milan and Venice: This is a great itinerary for travelers wanting to visit Prosecco Road or the Italian Lakes (Como, Garda, Iseo and beyond). Bergamo or Verona are both ideal for day or side trips.

Naples and the Amalfi Coast: Here, you should also enjoy Sorrento and the historical towns of Pompeii and Herculaneum, as well as coastal towns like Ravello, Positano, Amalfi and more. Day trips to Capri or Ischia from Naples are a must.

Genoa and Turin: This may be best for those having already visited other parts of the country. Foodies and winos will be in heaven in these less-touristy areas of Italy.

Southern Italy: Regions like Puglia are a little more complicated to get to and move around in. Life moves slower and is less organized in Southern Italy (that’s the beauty of it), and things like buses and trains may not always arrive on time, so it may be best to spend all your time down there and simply explore as you go.

How to Plan a Trip to Italy: Step by Step Guide • Winetraveler
Cala Corsara, Maddalena archipelago on Sardinia island, Italy.

The Islands are Worth Visiting Too

Italy has some incredible islands, the most recognizable being Sicily and Sardinia. The aforementioned spots of Capri or the more local Ischia and even the tiny island of Procida are easily accessible from Naples. Ponza is an under-the-radar island off the coast of Rome, and the harder to reach but the gorgeous island of Lampedusa is off the coast of Tunisia. Nature lovers will enjoy the Tremiti Islands in the Adriatic Sea off the country’s Puglian shores.

The islands, besides having some of the best beaches in Europe (maybe even the world) are also the way to go if you really want to explore Italian culture, cuisine and lifestyle. Similar to southern Italy, prepare for a different way of life on many of the lesser-visited islands. Prepare for “island time,” low levels of English among the locals and limited public transportation.

Find the Closest Wine Region

Once you’ve decided on your main destinations, it’s time to involve wine. Luckily, vineyards grow all over Italy, so it’s easy to explore a wine region during your visit or taste specific types of locally-grown wine no matter where you go. Here are some ideas to get you started:

If you’re heading to Rome, visit Lazio or Abruzzo.

If you’re heading to Milan, visit Franciacorta.

If you’re heading to Florence, visit Chianti.

If you’re heading to Turin/Genoa, visit Barolo or Asti.

If you’re heading to Sardinia, visit Carignano del Sulcis.

If you’re heading to Naples, taste the Lacryma Christi (Tears of Christ) wine, cultivated on Mount Vesuvius.

If you’re heading to Sicily, taste Nero d’Avola.

If you’re heading to Venice, visit Prosecco Road.

If you’re heading to Puglia, taste Primitivo.

How to Plan a Trip to Italy: Step by Step Guide • Winetraveler
Mornings in Amalfi.

Use All of Winetraveler’s Resources 

The Winetraveler team has traveled extensively throughout Italy — while simultaneously drinking as much wine as possible. Make sure to check out all of our Italian content, which can help you make your itinerary, find the nearest wine region, or know what to do, see, eat and drink while visiting some of the country’s most popular spots. Also, download the free Winetraveler App to research, sort, save and create hundreds of itineraries to visit Italy efficiently.

A Wine and Food Lover’s Travel Guide to Central Italy

10 Authentic and Essential Things to Do in Naples

A Guide on How To Spend 3 Days in Rome

A Cinque Terre Travel Guide

10 Authentic and Essential Things to Do in Milan

Italy’s Best Kept Secret: Sicily

Discovering the Captivating Puglia Region

10 Charming Italian Towns to Visit if You Love Food and Wine

Get Articles Like These Directly in Your Inbox!

Subscribe to Winetraveler and receive notifications when new articles are published. It's free!

Leave a Comment, Ask a Question or Share a Review

One Comment

  1. In some ways it seems overwhelming to know where to start when planning a trip to Italy! I like how you’ve summarized some of the wine regions/types to explore from certain “jumping off points” in the country. Love how there are vines and wines to see no matter which direction you go!

Share to...