Italy Travel Planning

Here are my tips on planning a trip to Italy. When I start planning my own trip I think of it in steps each time and I want to share that process for any who might be thinking of planning their own. In fact, I may host a bespoke trip in 2022 for a small group of people who want the historical/modern experience married along with all the secrets I’ve discovered during my 8 trips there over the past 10 years.

  • When to go
  • Needed documents
  • Itinerary choices
  • Apps and spreadsheet advice
  • Internet and data plans
  • Packing
  • Final thoughts

When to go? My personal preference is to go off season so that places are not as crowded and prices are lower. Peak season is basically from Easter to Labor Day (American holiday at the beginning of September). August is Ferragosto and Italians ALL go on vacation so the popular destinations will be packed. Also the summer can be HOT & HUMID depending on whether you’re in the mountains or alpine regions vs the southern area and islands. I recommend visiting during Carnevale (Mardi Gras), before Spring Break, or after Sept 1. This gives you optimum opulence and festivities during Carnevale or times that are cooler and less busy but still usually sunny. This means especially perfect weather in Emilia-Romagna during my typical Sept 20-Oct 10 visit.

The documents you need are your passport, driver’s license (for car rentals), proof of vaccination and – at the time of writing this article – recent negative COVID test results (check the US Embassy in Italy website for the latest requirements). US citizens can stay up to 90 days in Italy without a visa but you must have 6 months validity on your passport. More info on travel advisories and documents needed can be found at the US Dept of State website for Italy.

When starting to develop your itinerary the first thing I do is choose where I’m going to fly into. I usually choose Venice Marco Polo (VCE), Milan Malpensa (MXP), or Bologna Marconi (BLQ). Taking the train into Ferrara, where I usually base my travels, is quick/easy from all of those airports. I also consider deals flying into Rome Fiumicino (FCO) because my nearest US airports typically have prices that are very low during the fall to fly there. Use Google flights and Skyscanner to search for the best combination or direct flight option for you. You could set up an alert on Skyscanner when you decide on the month you wish to go and wait for the price to drop. Use a private browser setting to search for flights because ticket sites tag you as a user searching for a flight and will offer you increased prices the more you check for updates.

A good rule of thumb for traveling to the Italian Peninsula is to avoid packing too much in. Transit times and the distances from north to south in this country can complicate a packed itinerary. Italy is divided into regions, provinces, and communes (in order of largest to smallest). For a 4-5 day trip choose one comune to focus on. For a week to 10 days you could fit in up to 3 comuni across a province/ region or two. For my typical 2-week trip I cover 3-4 comuni across nearby regions. The one trip I stayed 5 weeks I comfortably covered 6 comuni resting in Ferrara in between.

Regions of Italy

I plan my trips using the items I’m researching and their archive/ library locations, blog recommendations, word of mouth from friends of friends, and guidebooks. My favorite guidebooks are published by Lonely Planet, DK Eyewitness, and Rick Steves. You should start making reservations for hotels, rental cars and flights 6-12 months in advance, for trains – if you want – I’d say book 1-2 months ahead (but I usually get my tickets at the station). Trenitalia and Italo offer basic, first class, and high speed trains across the country.

Look at reviews for hotels on TripAdvisor, Booking.com, and Airbnb when you are researching which hotels to reserve. Keep an eye out for agriturismo opportunities, which are offered by Italian farmers and provide a more intimate experience than staying at hotels or airbnbs.

If you are going to stay in major cities (comuni) and towns then train is the way to go. If you plan to visit the countryside I suggest you rent a car (rent the smallest you can fit your luggage in). Google maps and the Citymapper app both offer GPS directions and offline downloads so you can navigate without using data.

If you are interested in small tour companies to give you insight into one of the cities you’ll be visiting I recommend The Tour Guy and Walks. In Venice I like Monica Cesarato walking tours. In Romagna this company offers Caterina Sforza tours! Airbnb also offers “experiences” led by their hosts.

Apps and spreadsheets that use while in Italy are as follows:

Google sheets (be sure to ‘make available offline’) for itinerary info like venue, address, reservation number, open hours, etc.

Citymapper app for directions (driving, train, and walking directions!).

TripIt or Tripcase apps to save all my reservation and flight info direct from email.

Conversion app for Euro to dollar, miles to km, and gallons to liters.

Weather app like Dark Sky or Accuweather.

For phone data I get an international plan for unlimited texts overseas and rely on wifi at hotels to download any info I may need. Some of my friends buy a $40 sim card when they arrive in Italy at the Coop so they can swap it out in their phone and use data on the go.

When packing remember that elevators, escalators, and people movers do not really exist over there. You’ll have to get your luggage up (and down) various stairs at train stations, hotels, and airports. You will also have a TINY car (trust me, don’t go for renting a large car because you’ll either have no where to park or have to deal with hostile Italians sneering at you because you take up two car spots. Take the least you can, carry on site is recommended. Do not forget these essentials: travel plug adapter/converter, packing cubes for organization, taking a credit card that doesn’t charge Euro conversion fees or ATM fees & power bank for recharging on the go.

Finally, remember this is going to be fun. Prepare as well as you can and then let it go. Whatever happens over there can be handled by a trip to the Coop 🙂


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