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What I Wore & More in Italy
My husband and I celebrated our 10th wedding anniversary in August 2020. We had grand plans to travel to Italy to celebrate. COVID had other plans for us. Our trip was put on pause and we were finally able to travel to Italy last summer instead. We spent 10 days in Italy—divided across Rome, Florence and Tuscany—and had a travel day on either end of that
If you traveled at all last summer, especially internationally, you may recall that there were issues with luggage at many airports due to a lack of baggage handlers and masses of people traveling once again. I didn’t intend to carry on my luggage but I was so paranoid about my bag getting lost that I was determined to make it work. Carrying on 11 days’ worth of clothing and shoes was easier than I thought! We did check a mostly empty piece of luggage (and threw an Airtag in it for good measure!) in the event that we would buy things in Italy and need more space to get everything home, but everything I planned to wear was in my carry-on bag. This is one of my proudest packing feats!
My type A personality made this a little bit easier for me and there may or may not have been a spreadsheet involved… but the top things that helped were things I’ve shared here previously, particularly strategizing what I was going to wear each day based on what sights we were seeing, being willing to repeat clothes throughout the trip and limiting myself to packing only pieces I knew I would absolutely wear. Because travel was in full force last summer, seemingly for the first time since COVID, I also booked all of our attractions well in advance of the trip, so I knew exactly what we’d be doing each day (and in some cases, where we’d be dining).
What I Wore
Everything you see here was in my carry-on bag, with the exception of the hat (which I literally carried in my hand) and the stacked-heel sandals; I packed those in the one piece of checked baggage because I wasn’t sure if I was going to wear them (I didn’t) so I wasn’t too concerned if they were in a bag that got lost or delayed. I wore every single piece of clothing you see, some pieces way more than others.
My strategy for the mix-and-match pieces you see on the left was to focus on neutrals that could easily be paired, along with stripes and a print for some variety. I wore the grey Chaser linen-blend raglan top, the black and white Madewell Whisper cotton v-neck tank tops and the beige and white striped flutter-sleeve top from Target the most. Because the tank tops are so lightweight, I was able to easily hand wash them in our hotel room sink and air dry.
I intentionally went heavy on dresses because I knew it was unusually hot in Italy (and paired them with Thigh Rescue or Cooling shorts). The olive, blue and red dresses are all linen-blend (and from Target) so they were obvious choices. The black dress is one of my beloved H&M kaftans (which sadly, is no longer available because they seemingly only have oversized kaftans this year which is a whole other topic) and although you can’t tell, it is kind of a silky, slightly shiny fabric which lent it to being dressed up a bit. Plus, I appreciated the roominess for carb-loading. I wore those four dresses most frequently. The botanical Johnny Was Strass wrap maxi dress is a piece that I only wore once and as much as I love this dress, I regret taking it as it just wasn’t practical and because it’s a maxi dress, it took up a decent amount of space in my luggage (even rolled). I got a bit more wear out of the cheetah-print Velvet by Graham and Spencer Amaury wrap dress but it was another piece I just didn’t wear quite as much.
As you can see, I only took three pairs of shoes and ultimately only wore two of them! While it might have been nice to have more options simply for variety, I didn’t need more shoes, and chances are, I wouldn’t have worn them anyway as we did so much walking and I really needed comfort. My Veja Urca sneakers and Birkenstock Arizona sandals in metallic copper were all I wore all over Italy. Lastly, I packed a straw fedora which I wore a lot. It was so hot and my hair was in a ponytail most days, so the hat added a little style and kept a bit of the sun off my face.
That’s it! This experience definitely solidified “less is more” when it comes to fashion for me. Although I did get a bit tired of wearing the same things, it made it easy to get ready because I didn’t have too much to choose from and I could focus my energy on important things—like where to get our next bowl of pasta. I relied on jewelry to add interest, too.
… And More
Want to know more about my trip beyond the fashion? Read on for where we stayed, what we did and where we ate in Italy.
Day 1 | Rome
We had an overnight flight from the U.S. and arrived in Rome early morning. We took the regional train from the airport (FCO) to Trastevere station since that’s where our hotel was, and then we made the very unwise decision to walk from Trastevere station to our hotel; it was about a 30-min. walk. It was hot. We had three pieces of luggage plus two backpacks. 10/10 do not recommend. I’m sure we were quite a sight when we arrived at the hotel! Because it was too early to check in, we stowed our bags, quickly changed in the bathroom and forced ourselves out and about to adjust to the time difference. We walked across the Tiber River to Campo de’ Fiori where they were having a big Friday market with lots of pasta, limoncello, hats, linen clothing and fresh fruit. We walked through Piazza Navona and then towards the Pantheon mainly to get our bearings since we had a Pantheon tour scheduled for the next day. We crossed back to Trastevere and had lunch at a pizzeria—the first of many prosciutto and melon plates and pizza! Oh, and an Aperol spritz for me and Peroni for my husband because… vacation. We made our way back to our hotel and took a much-needed respite in the AC before showering and heading downstairs for aperitivos in the gorgeous courtyard.
We chose to stay in Trastevere because of its location (extremely walkable), restaurants and neighborhood feel. Some online research led me to Donna Camilla Savelli, a beautiful former convent dating back to the 1600s. It was uncharacteristically hot for Rome, even in late July, and luckily the AC in our room was pretty powerful. We had breakfast daily as well as aperitivo (along with the resident pigeons) in the courtyard every day, plus there was a terrace that offered picturesque nighttime views of Rome—something that pairs beautifully with an after-dinner limoncello.
I did a lot of restaurant research before our trip and knew I had to try the cacio e pepe in a parmesan crisp bowl from Roma Sparita; it didn’t disappoint, and we were quickly reminded how affordable it is to eat good food and have a bottle of wine in Europe. We skipped dessert at the restaurant and walked to Otaleg (“gelato” spelled backward… see what they did there?) because I read it was the best gelato in Rome. I’m sure there are countless “best” gelatos in Rome but we decided to see what the hype was all about. There was a line out the door and while I’m not one to wait in lines… when in Rome… It was worth it.
Day 2 | Rome
Our first full day was dedicated to sightseeing. We started with a self-guided audio tour of the Pantheon which I would recommend. It was roughly an hour and gave me just the right amount of info I wanted—not too much, not too little. We booked our tickets online weeks in advance but they weren’t strict about the start time; we went about an hour before our actual reservation and it was no problem. From there we walked to the Trevi Fountain for the obligatory photo but failed to get coins by that point so we weren’t able to make a wish(!). The area was filled with tourists so we didn’t linger but instead headed to the Spanish Steps which were also crowded—both as to be expected. We walked to the top and took in the views before ducking into the Keats-Shelly Memorial House next door. Admittedly, the museum AC was an added bonus. We walked back to Trastevere and had an unremarkable lunch at a place I can’t remember before retreating to our room for rest and AC. Although I live in Austin where it’s brutally hot all summer long, I don’t spend those hot summer days outside walking miles and exploring, so it was draining. We couldn’t resist aperitivos at our hotel before walking just around the corner to Zia for dinner. We wanted to have one really nice dinner while in Italy and Zia checked that box.
Day 3 | Rome
It was another hot day, so I was glad that our three-hour walking tour of the Colosseum and Roman Forum was in the morning. Even still, there’s not much shade to be had in the Roman Forum which is where the tour began. Our tour guide was very passionate about the Colosseum and Roman history and he had a lot of opinions on things; well-suited for his job. For me, it was too much and I was ready for lunch and a cocktail when the tour ended. It was my second time seeing the Colosseum and Roman Forum but my history-buff husband had never been and absolutely needed to see it.
We didn’t want to eat somewhere right next to the Colosseum but we didn’t really know where we were going and we were hot and tired, so we ended up nearby at Benso. And you really can’t go wrong with prosciutto and melon or caprese!
That evening we didn’t have plans for dinner so we walked around Trastevere casually and stumbled upon Dar Poeta. There was a slight wait for a table but when you can sit on the curb with a beer in hand and people-watch, time goes quickly. We had the best pizza of our trip there which was a nice way to round out our time in Rome.
Day 4 | Florence
It was time to move on to Florence. We took a taxi to Termini Station to catch the Trenitalia (booked in advance). The train ride from Rome to Florence was about an hour and a half. We arrived at Santa Maria Novella station around lunchtime and it was a very short, easy walk to our hotel, Hotel Spadai, which was just around the corner from the Duomo. We stowed our bags and walked to Trattoria Marione for lunch which felt like a beloved local spot; the day’s menu was scrawled on a piece of butcher paper and posted outside the door and it was packed inside with what didn’t feel like tourists. I had a very memorable plate of pasta piled with truffles.
We had booked tickets in advance that gave us access to the Cathedral, Baptistery, Duomo, Giotto's Bell Tower and Opera del Duomo Museum for three days, so we decided we’d start with the Bell Tower. We weren’t too far up the ~400 steps and it was incredibly hot and stuffy. I started to get extremely claustrophobic so I aborted the mission and left my husband to climb it on his own! It was so hot that by the time he finished, we didn’t have energy for much else, so we retreated to our hotel for a little rest followed by aperitivos. That night we walked up to Piazzale Michelangelo which was worth the hike; it was so picturesque. We knew we’d be back before we departed Florence.
Day 5 | Florence
We took in the Uffizi which was our first taste of art in Florence. But really, the city itself is a work of art. It was both incredible and overwhelming and by the end, we joked, “There they are again,” in reference to yet another painting of the Virgin Mary and Jesus. Amongst my favorites, though, was Piero Del Pollaiolo’s seven virtues. After the museum, we walked across Ponte Vecchio to Gelateria Santa Trinita. It would be the first of several visits. Then we went to the Cathedral to see the Duomo from the inside (we did not climb it) and strolled around a bit before stopping at Enoteca Alessi for lunch—a delicious meat and cheese board along with a glass of rosé for me and a beer for my husband.
We had plans to walk to the Boboli Gardens that evening and then have a later dinner, only to find out that the gardens closed about five minutes before we arrived. As we started to make our way back to the other side of the river we stumbled upon Tuscan Taste, a little shop with beer, wine, meat and cheese which also offers cooking classes. We sat and enjoyed food and drinks and spoke with one of the owners; it ended up being one of the more memorable evenings of our trip. We made our way back across the river and stood in line at All’antico Vinaio, the famed sandwich shop, and got one to share. Ours had prosciutto, honey, pecorino and of course truffle. We sat on a curb and ate it while listening to a symphony perform at Palazzo Vecchio. Florence was alive.
Day 6 | Florence
Our last day in Florence started at the Galleria del Accedamia. It felt much more manageable than the Uffizi and seeing Michelangelo’s David was a highlight. Because we were still dreaming about the gelato we had the day before, we made another trip to Gelateria Santa Trinita. It was just what we needed to fuel us for a stroll through the Boboli Gardens. It was so hot and had been for some time, not to mention there hadn’t been much rain in Florence recently so there wasn’t too much in bloom. We walked back closer to our hotel for lunch and I wish I could remember the name of the place where we ate. We had the nicest server who treated us to limoncello to finish our meal. Since it was our last night in Florence, we chose to visit Piazzale Michelangelo one more time for sunset. We stopped for aperitivo before making the trek up the hill and once there, enjoyed drinks and a one-man band. It was very crowded. We were in no rush so we leisurely strolled to find a spot for dinner and ended up at Coquinarius, which ironically was across from where we had eaten lunch. It was extremely busy at the popular 9:00 dinner hour but our lengthy dinner was okay with us so that we could linger on our last night.
Day 7 | Tuscany
We took the train from SMN to the Florence airport to get our rental car which could not have been easier. Then we drove about two hours to Tuscany stopping first in San Gimignano. It was such a cute little town and we had the best lunch at Spizzicheria Le Chicche Toscane. More prosciutto and melon and bruschetta (with prosciutto because can you ever have too much?). We wished we had more time to explore San Gimignano but we had plans to visit a winery called Tolaini, which produces chianti, before heading on to our hotel. It was off the beaten path but we’re happy to have visited as we learned there are some chiantis that we enjoy. After our tasting, we made our way to Locanda in Tuscany, the inn we stayed at in Val d’Orcia. We were upgraded to a junior suite which was both rustic and luxurious and offered plenty of space. It had a gorgeous fireplace which we of course didn’t have the opportunity to use. That night we had our first meal at the property’s restaurant, Taverna di Mozart; I had steak tartare, deconstructed lasagna and tiramisu that we continued to talk about after we checked out a few days later.
Day 8 | Tuscany
Our full day started after breakfast when we drove to Arezzo. We walked around the city a bit and popped into a few shops before heading to Anghiari for an olive oil tour and tasting at Ravagni 1421. We met Francesco Ravagni at the olive oil mill; there were two other couples/families there for the tour, though they had been before. Francesco showed us the equipment they use and told us about preserving the traditional process for olive oil-making; they don’t want to be the best olive oil in Italy but they want to stay true to the craft of making it. The tour itself was relatively short, then we all got into our cars and followed Francesco on his motorbike up a seemingly never-ending mountain. We eventually ended up at his home which overlooked the valley and Lago di Montedoglio. It truly looked like a postcard. The dining table on the patio had been set and included a variety of olive oils and balsamic vinegars. We sampled them as well as Francesco’s wines (and eventually, grappa). His wife prepared what was described as a “light” lunch which was anything but! It was filling and delicious—pasta, garden fresh vegetables and bread. We spent hours on the patio eating, drinking and talking with Francesco’s other guests. It was such a memorable day and a highlight of our entire trip. Francesco was so knowledgeable, friendly, hospitable and entertaining. We managed to find our way back down the mountain and made a somewhat quick stop in Montepulciano where we had planned to do a wine tasting but by that point in the day the wineries were closed, so we opted for aperitivo at the first spot we found.
Day 9 | Tuscany
It was our last day in picturesque Tuscany and we opted to make it a slower, more relaxing day. We slept in and spent some time at the pool after breakfast. The resort arranged a wine tasting for us in Montalcino, so we had lunch first at Belvedere Bar which overlooked the valley. After lunch we went for a tour and Brunello tasting at Podere Le Ripi. The wines were tasty and pricey! We relaxed with more pool time and aperitivo before our last dinner that evening at Taverna di Mozart. We could’ve easily spent a week just in Tuscany itself!
Days 10 & 11 | Tuscany to Rome to Home
Our journey back to the U.S. was really a two-day process. In Tuscany, we got up early to drive to Florence to return the rental car, then took the train from the airport back into the city to SMN. We had a few hours before our train departed so we parked ourselves at a cafe near the train station and had brunch. Once we got to the train station we found that our train had been delayed, so there was quite a bit of waiting time at SMN which was very hot, crowded and chaotic. The train back to Rome was very crowded, too, and so was the taxi stand when we arrived at Termini Station.
Our last night in Rome we stayed at Le Meridien Visconti which wasn’t too far from the Vatican or Trastevere, but we really chose it because we could use Marriott points for our room. Since it’s a Marriott property, there were a lot of Americans there! It was fine for a night. We had aperitivo–the last of our trip–at the hotel and then walked to Pizzeria Malaterra for dinner.
The next day we only had time for a café and one last quick stroll before heading to FCO to return to the US.
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