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In 2020 the world was smacked in the face by COVID-19. Freedoms we took for granted on a daily basis – the ability to see friends, eat out at restaurants, attend live sports, and especially, travel – were limited. As much as I love post-apocalyptic fiction, I don’t ever want to live through that again. My life needs to be full of trips to Italy.
When I say Italy needs to be your first trip post-COVID-19, that’s honestly a bit tongue-in-cheek. I would love for Italy to be your first trip you take, but I’ve learned over the past year that even a trip to a mid-western city 3 hours away can be a delight. So I encourage you to use Google Flights, monitor Spirit’s $9 Fares, watch Frontier’s Discount Den… do whatever you need to do to find cheap flights, and take them.
Once you are ready to travel internationally, Italy should be at the top of your list… if not, I highly recommend London, England and my London in 24 hours itinerary.
Why Travel to Italy?
Simply put: Italy has something for everyone. Food, architecture, history, religion, art, even beaches. And I’m sorry to the French out there, but Italian wine is the best in the world. Chianti must be experienced with every meal.
The Colosseum, Sistine Chapel, the Vatican, the Spanish Steps, Pantheon, Trevi Fountain and so many more. It’s hard to look around Rome and not see a famous landmark. For this reason, you can also hit the main sights in just a few days. My suggestion:
- Take the Colosseum underground tour. The guides are excellent, and do a marvelous job of painting what it would’ve been like to enter the Colosseum 2,000 years ago. Later, hear the stories of Romulus and Remus as you tour Palatine Hill.
- Tour the Vatican with a Skip the Line Ticket. Look, even if you’re not religious, if you’re in Rome, you need to tour the Vatican. Note, that prior to COVID the Pope would give mass on Wednesday mornings in St. Peter’s Basilica. This meant tours would skip that portion. If St. Peter’s is a must, you’ll want to avoid booking the tour on a Wednesday.
- Spend your 3rd day seeing the rest of the sights. The Spanish Steps, the Pantheon and Trevi Fountain are all within walking distance of each other.
Venice is my second favorite city in Italy. And that’s as a single guy. Venice is actually much more easy to do as a self-guided tour than Rome. First if you’re unaware, Venice is made up of several different islands. I suggest taking one day to visit each one. Outside of the main island, you’ll love the glass making in Murano. The colorful houses of Burano.
Next, explore the main island – “Centro Storico.” Piazza San Marco is beautiful, and St. Mark’s Basilica is 79 years older than Paris’ Notre Dame. Climb the bell tower for me, please. I was too
hungover lazy to do so and I regret it now.
Look, I’m going to be honest. My favorite part of Florence was the wine, and gelato. But there is actually a lot to see and do in Florence. And, I really don’t think you’ll have a better meal anywhere else in the world.
Florence, Firenze as it’s known to Italian speakers, has the Statue of David. The Piazzale Michelangelo is well worth the hike – and I promise you, one of the best meals I’ve ever heard in my life was at the nearby Bastioni di San Niccolo.
The odd thing, I know I’m supposed to find the architecture in Florence so incredible. But it just didn’t do it for me. Roman, Flemish… I’m in. Florence, not so much.
OK, if you flew into Milan. Check out the Duomo di Milano. Purchase the tickets to climb to the rooftop. If you love shopping, you have even more to do. Unfortunately, outside of that Milan really doesn’t have a lot going on, and I didn’t feel very safe in Milan. For that reason, I suggest using Milan for one thing… going somewhere else in Italy.
Note: If you are into art, you can see Da Vinci’s Last Supper at Il Cenacola.
Cinque Terre, Italy
The highlight of Italy. The destination I day dream about. If I ever go silent mid-conversation, it’s because I’m pretending I’m in Cinque Terre.
Cinque Terre means five lands, and is located in the Italian Riviera. It’s five villages that are only accessibly by train. Each city is linked together by trains or by hiking trails. And it’s beautiful. It’s incredible. It’s everything you dream of in a vacation.
Hiking. Beaches. Gelato. Wine. Fresh oranges, lemons, and absolutely delicious food.
You can purchase a ticket to hike the trails linking each of the cities. Note, that for preservation not all trails are always opened. Some will be shut down due to too much traffic, recent rainfall… etc.
The five cities are as follows.
I recommend spending a day hiking and visiting each of the cities in Cinque Terre. If you want to really relax, and see the villages, spend two. You won’t regret it. Each village has its own feel. Lonely Planet has an excellent write up on each one, so if I’ve convinced you to give Cinque Terre a try, I’ll let Lonely Planet describe each village in better detail!
Other Italian Cities
Of course there’s many more cities in Italy that you could travel to. Honestly, Pisa – the leaning tower is beautiful, but there’s not much else to do there. Lucca is a fun stop if you do visit Pisa. Bike around the ancient city wall. However, neither are absolute a must-see.
… and there’s Bologna, Sardinia, Lake Como, and so many more. Unfortunately I can’t speak of them, as I’ve yet to see them. The Amalfi Coast is high on my list, but I can’t comment on it yet. I hope to do so soon!
Italy Trip FAQs
If booked ahead, Italy’s train system is affordable, and easy to navigate. I suggest flying into either your favorite destination or the most affordable. If you need a place to start, Milan and Rome are the two largest airports in Italy. You could also investigate Florence.
For the most part Italy is a safe country to travel to. You’ll run into some beggars, and scams on the street, especially in Milan. Just keep only your credit cards and cash absolutely required on you, and keep everything else in your hotel safe. Don’t show any extravagant signs of wealth and don’t walk down back alleys at night.
If you want my opinion: Rome and Cinque Terre. Nothing else matters.
Yes, use public transit. When I visited Italy in 2017 and 2019, they did not allow for Ubers. This meant that cabs were incredibly expensive. I suggest using bikes, public transit or my favorite – purchase a day pass on the city sightseeing buses.
No, nor should you expect them to. Most will try, but you may need to use body language and/or point to what you need. With that said, I wouldn’t anticipate this ever being a problem. There are enough English speakers in the country that it shouldn’t take away from your trip at all.