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How to Spend 20 Days in Italy

I’ve wanted to go to Italy for as long as I’ve known I was Italian. So, pretty much always.

When I was deployed last year, my now ex-boyfriend & I started talking about trips to take after the deployment. He’s Italian. I’m Italian. We’d both always dreamed of visiting Italy, so Italy it was.

We spent the next few months trying to decide where we wanted to go. We wanted to experience different parts of Italy, but we didn’t want to feel too rushed. So we spent months – actual months – deciding on an itinerary and then, in May, we spent almost three weeks exploring Italy.


DAY 1-2: JFK > FCO || Overnight & direct. Beautiful, except for the terrible child who screamed for 67% of the flight.


// Rome is huge and there’s so much to see. We spent four nights in Rome, longer than we spent anywhere else, and it was just the right amount of time to get a generous introduction to the capital city. I’d definitely visit again, but I’d spend my time further away from the main tourist attractions.

THE BEST: Eating Cacio e Pepe & Spaghetti Carbonara. Testing out our Italian language skills. The Colosseum. Walking up 500+ stairs to the top of St. Peter’s Basilica. Pizza. Walking across the Tiber and around Trastevere. The Pantheon.


// Umbria is beautiful. It’s wilder than its neighboring cousin, Tuscany, but just as lovely. Assisi gets busy during the day with bussed-in tourists, but the nights tend to be more mellow. We had one of our best and most authentic meals in Assisi.

DAY 8 SIDE TRIP: SPELLO || We had a car, so we wandered south to Spello on our middle day in Assisi, just to get a feel for another city within Umbria. It was a Monday, typically a slow day in Italy, so the city was eerily quiet. We walked around. Met some cats. Drank some wine. And left.

THE BEST: The Basilica di San Francesco. Dinner at Trattoria Da Ermino. Walking up an actual mountain to Eremo delle Carceri, a sanctuary visited by St. Francis of Assisi. Our beautiful Airbnb.


// On our way to San Gimignano, we pit-stopped in Siena for a few hours and it was magical. I really liked the way Siena felt. It was cool and trendy and had a modern feel while still being this incredibly beautiful Old World city.

THE BEST: The Siena Cathedral. Shell-shaped Piazza del Campo. The Palazzo Pubblico. The escalator from our parking area up to the city center.


// When we found our B&B we starting freaking out. It was beautiful, overlooking the grape-vined hills of Tuscany. We both just started laughing, thinking there was no way our home for the next three days could be so beautiful. But it was. Plus, it was just a five minute walk into San Gimignano.

+ DAY 11 SIDE TRIP: FLORENCE || You guys. I didn’t like Florence. Maybe it’s because we didn’t spend much time there, or because we didn’t spend a night there, but I just didn’t like it. It was hot, crowded and everything we wanted to see required waiting in a stupidly-long line.

THE BEST: Our B&B, because really – beautiful views, a comfy bed and fresh-made breakfast every morning. Seeing the David. Wandering around San Gimignano after all the other tourists left for the day. Gazing at the Tuscan hills.


// We smushed in a day trip to Cinque Terre toward the end of our planning process. We wanted to see the coast, and Cinque Terre made the most sense. We stayed in La Spezia, which saved us a ton of money, and were right next to the train station so we could get to Cinque Terre in less than half an hour. First, we trained to Monterossa, hiked to Vernazza, then trained to Manarola. All the cities are beautiful and they’re all different too. But crowded. SO CROWDED.

THE BEST: Hiking from Monterossa to Vernazza, even though the trails were packed with people. Watching the sunset in Manarola. Exploring the coastline.

DAY 13-15: MILAN

// Milan was primarily on our list because my ex had family there. In researching where to go, we read mixed reviews about Milan. But we both really liked it. It was beautiful, full of art and good food, and it had a unique mix of modern structures and ancient history.

THE BEST: Going out with local Italians to experience the city & getting an impromptu tour at midnight. Visiting the Duomo and climbing to the top to see the city laid out around us. Walking around the city without much of a plan. Peeking onto ancient Roman ruins hidden beneath a modern square.


// We pit-stopped in Verona on the way to Venice, stowing our bags at the train station. I could have spent a few days in Verona, I think, eating and drinking and wandering around.

THE BEST: Seeing the Arena, built in 30 A.D. Checking out Juliet’s House. Lunch and prosecco at Terrazza Bar Al Ponte, with an incredible view of the river.


// We probably spent whole weeks debating Venice, but ultimately, we were so glad we went. We avoided the crowds, for the most part, and hid from the major tourist attractions, opting to get lost on side streets instead.

+ DAY 16 SIDE TRIP: NAVARONS || We rented a car for a day to pop north to visit the birthplace of John’s mother and grandmother. It was magic, both exploring a tiny Italian village and watching him discover it. He was able to stand in the place his grandparents were married and it was just very, very special.

THE BEST: Getting away from cities and visiting Navarons. Eating a stupidly amazing meal in Meduno, at La Stella. Getting lost on Venetian side streets. Eating cicchetti.

On the 18th day, we went to the airport. We checked our bags and went through security and got in line to board the plane. But then our flight was cancelled, about five minutes before it was supposed to take off. So instead of flying home, we spent two or so hours waiting in line to rebook our flight home, took a taxi to our hotel and napped like champions and did absolutely nothing for the rest of the day except for eat our provided dinner at the hotel.

Since we originally booked a direct flight home, that’s what we wanted. The next direct flight JFK wasn’t for two more days, we ended up with a bonus day in Italy.


// We didn’t want to go back to Venice, since we’d already said goodbye to it once, so we hopped on a boat and headed to Murano and then, later, to Burano. They’re both beautiful islands with their own unique culture. I’d highly recommend a side trip for anyone with a spare day in Venice.

DAY 20: VCE > JFK || There were only eight of us on this plane, all displaced from the earlier cancelled flight. Even though the plane was empty, Delta still wouldn’t let us sit in first class, but we each had a few rows to ourselves and – best of all – there were no kids on the plane.

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