6 tips I learned traveling to Italy in July 2021

July 21, 2021


  • Keep your trip expectations low.
  • Take photos of everything.
  • Visit smaller towns.
  •  Triple check entry/exit requirements.
  • Create backup plans.
  • Allow for spontaneity

Keep your trip expectations low

Why would I lead with this? Well, simply put, if you have low expectations it’s easy to surpass them. To give you a bit of background, my wife and I weren’t necessarily planning on taking a trip to Italy in early July until a just a few months prior. Normally, for international travel, we often book 4-6 months in advance and do quite a bit of planning. Obviously every thing is different with pandemic international travel, and we don’t have that luxury anymore. Going into this trip, I told Sarah that we should and will expect it to not be a perfect trip. That we will run into problems. That we may have trouble getting into Italy, or even returning to the U.S. Keeping your expectations in check and really just having a low bar for vacation success really helped us in our perspective and everything that did end up being a challenge was simply expected or ‘par for the course’. Here’s a few things that “went wrong” or were really just small challenges:

  • Chaotic boarding process at JFK to Italy. We had to fill out a ‘self declaration form’ at the airport gate, take our temperature and have our ticket stamped by the temperature taker guy, and wait in two different lines to have our documents checked by gate agents. There was little to no signage, and it was a hot mess of people simply wanting to board a plane.
  • Landing in Italy was an absolute breeze. Rolled right through customs or whatever it was – barely checked any documents. I think since there was so much clearance on the flight over they figured it was fine..
  • We overshot our train ride going from Milan to Lake Como by a stop. If we went 1 or 2 more stops, we would have been in Switzerland and there were all of these signs that said you couldn’t come back into Italy from that route. Who knows if that was the case, but we didn’t want to find out. We ended up getting off the train at the last stop before Switzerland, switching over platforms, not paying for the ticket because we were going back 1 stop to Lake Como. In our defense the electronic sign in the train malfunctioned and showed the wrong stop and the next train was arriving. So outside, I knew we were at Como. But inside the train, it said we weren’t there yet…
  • Rest of the trip was mostly a breeze.
  • Unexpected covid-19 test required for re-entry (oops, didn't see about that one!)

Waiting to board the plane at JFK!

Take photos of everything.

Your covid vaccination card. Your self declaration forms. Your passport. Your drivers license. The rental car. Some of the receipts you might throw out for big purchases, like from hotels. Your insurance card. We took photos of almost everything, and I’m glad we did. Because some of these forms you have to pull up using the internet and either a browser or your email – and can’t always rely on it. You might lose the forms of course. It’s just good practice I feel. Of course some folks might think it’s an identity and security issue, but I felt more comfortable doing so. I feel it was better to be safe rather than sorry. I only have 1 single vaccination card, and its of questionable material with hand written ink. It could easily wash out some of the numbers and letters and god forbid some gate agent try to tell me they won’t accept something. Well I have proof!

And I couldn't resist taking photos like this amazing single shot of espresso and a chocolate croissant. Courtesy of Milan. It was fantastic!

Visit smaller towns.

Everyone always wants to visit Rome, Florence and Venice when they go to Italy. Sure, those are great to check off the bucket list. But the reality is that these places are often the most crowded, least local, and highest cost. You might as well go to Disneyland. Well maybe not quite, but you get the idea. I think in normal times heading to the big cities, especially if it is your first trip to Italy makes a lot of sense.

Who doesn’t want to see where Gladiator took place? But the reality is that these cities are where most of the tourists who do come to Italy will flock, and there’s still an aspect of health and safety to care about. There’s still a lot of unknowns with COVID-19 and things mutate and change, and efficacy of vaccines and how long they last aren’t exactly known down to the date – so head to smaller cities. You’ll have a better experience, and get a more local flavor. And oftentimes save a lot of money too. You can do what you will, but we had such a great experience going to small towns like Cortona and Orvieto.

Pictured above the quaint Tuscan town of Cortona, on a hill in a picturesque area.

Triple check entry/exit requirements.

This is a big one. Before you even think about booking a flight or hotels and activities, triple check whether you’re even allowed to enter that country or destination and what the rules and restrictions are. Beyond just being let in, it’s important to get a sense of the ‘on the ground’ situation. Is transportation going? Are restaurants open? Are masks required? These types of questions will help you decide whether you even want to visit somewhere in the first place and will also help dictate what you should bring.

Sarah and I used a free Google Chrome extension called Peanut, that simplifies the COVID-19 travel rules and displays them directly on top of Google Flights, Booking.com and Expedia. Peanut also showed me that I did not need a visa, which was helpful, and that the flight I was looking at wasn’t likely to be delayed. Of course, I still wanted to check other official sources and cross check, but at least Peanut gave me a sense of the ‘on the ground’ situation before booking. It showed me that restaurants were operating, transportation was working, and masks were required indoors. Highly recommend installing it now yourself if you’re planning any sort of trip, whether domestic or international soon. It can’t hurt and will work on top of the regular booking websites, so you don’t need to do anything special.

Peanut was a lifesaver. I still had to double-check and triple-check everything, but I booked my flight more confidently.

Create backup plans

What happens if Italy doesn’t let us out of the country because we contract covid-19 somehow, with a breakthrough infection or the DELTA variant? We would have to quarantine in a hotel for 14 days minimum. What would happen if we lost our passport or vaccination card? Or we weren’t able to get into the country at all? These were just some of the questions that we wanted to answer, or at least think about, before traveling. We made sure that our cat sitter would be able to stay longer in case of some emergency. We took our work laptops in case we needed to stay longer and had to start working past our vacation allotted time. We generally just planned a bit for the worst-case scenarios. I was mostly worried about who would take care of our cats and how the house would fare at home.

Allow for spontaneity.  

Every trip should bake in time for spontaneity! But traveling to Italy during the pandemic, it’s important. There may be places you visit that just don’t feel right, or activities you wanted to do that you may not be able to do. Or new activities that you didn’t realize you could do, that is now open. We strategically left several days without a hotel booked, which I’ll admit is a bit risky, but we felt it gave us the flexibility we needed to make decisions on whether to stay in certain cities longer or shorter depending on the vibe and how much we liked that city.

For example, instead of staying a night in Parma we decided to head straight from Lake Como to Cortona. It ended up being a super long day, but 2 nights in Cortona was absolutely magical. And we were thankful the amazing hotel we stayed at had availability. It was probably one of my most favorite hotel experiences anywhere in the world. And take one of the last nights for example – I was supposed to spend 2 nights in Naples. I drove in, and the vibe just felt off. It was completely different than the rest of Italy, and not in a good way in my personal opinion. So I made the decision to drive down to Sorrento, and had the most wonderful time at a villa overlooking the coast for the remaining two days.

Above all, the biggest recommendation is to savor the moment when you’re there, in Italy or anywhere. If there’s anything we have learned on this trip is that it was so nice to get out of the house, off the phones and social media and just experience another culture, another way of life again. It was refreshing to be crammed into a tiny seat in coach and stepping on sticky pee in an airplane bathroom. It was refreshing to experience the magic of airplane constipation and jetlagged naps. It was refreshing to forget to grab the highway toll ticket and have to pay the max highway toll of over $100 instead of the $8 it should have been. Most of our snafus were self-inflicting and we had a great time. And 6 things everyone probably already knows about Italy: The food was outrageously good, the people were warm and friendly, the scenery and outdoors were breathtaking, the history was old and intriguing, the gelato was way better than ice cream and the espressos way better than any coffee. What are you waiting for?

Drove a ferrari. It cost $350 for 20 minutes. Worth every penny!

The Duomo in Orvieto, Italy. How empty is that? 
Cortona, the most amazing small town. This is my favorite place in Italy, ever!
Infinity pool at the Hilton in Lake Como. Pricey, but worth it!

What are you waiting for?!

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