two weeks in italy

We went to Italy for 14 days days in July/August 2023 and had the best time. Here’s a rundown of where we went and where we ate:

Day 1: Flew into Rome

We spent just one night in Rome, choosing to keep our time short because we were there in 2013 and it felt less urgent to allot limited days towards. We stayed at the Westin Excelsior, which was lovely but please note for this and almost all hotels I mention that we choose hotels where we can apply credit card points to cover our stay, thus your calculations will be different.

We headed to Trastevere for dinner, but without having planned ahead, our options [next time, Da Enzo, Cesare ala casaletto!] were a little limited. We ended up with a solid suggestion from Rachel Roddy (thank you!) at Proloco Trastevere; we liked the pasta alla gricia a lot. I had hoped to get back to our favorite gelato from 2013, Gelateria del Teatro, but jetlag set in. It all worked out; we went to Gelateria La Romana and I will dream about the espresso whipped cream they dolloped on top for a long time.

Day 2: Rome to Tuscany

While my husband went to pick up the rental car, I took the kids on a quick zigzag tour by the Trevi Fountain to get one of my favorite things on earth, the espresso granita from La Casa del Caffè Tazza d’Oro (plus pastries and orange juices, fresh squeezed, for them) then more pastries for the road from Antico Forno Serpenti.

We stopped for a beautiful lunch outside, our first real Tuscan meal with wine and relaxed courses, at Podere Il Casale in Pienza, then headed to our rented house in Gambassi Terme, Florence. We had a fantastic dinner at La Vecchie Mura in San Gimignano (a dreamy carbonara, perfect melon and prosciutto, and more) and then gelato at Gelateria Dondoli — I loved the salty, intense pistachio.

Day 3: Panzano, partly

As a rule, if the house where you’re staying has a gorgeous pool, a pool that you chose because you travel with five children and four adults, you’ll need to write in some pool days. This was one. I made lunch and to nobody’s surprise, yes, the basic grocery store mozzarella, tomatoes, prosciutto, and pasta are better in Italy. We briefly stopped in Sambuca along the way and hit a playground, and had dinner in Panzano at Officina della Bistecca, the upstairs of Dario Cecchini’s butcher shop. My husband and I decided to share one vegetable and one meat menu and we were so glad we did; it was impossible to eat all of the meat one alone, and honestly even shared.

Day 4: Florence

I spent a full week in Florence in the early 2000s with my mother and I am convinced we visited every museum so between that and the number of kids with us, we decided to save art-gazing for another trip. We walked around on a very hot day, failing in a few ways: the Sant’Ambrogio market closed just as we arrived at 2pm (whoops), Vivoli Gelato, which had made me swoon with that viral affogato, was closed on Monday, as were several other gelato places on my list (heartbreaking), but we stumbled onto a fantastic lunch at Cibrèo Caffè, with perfect salads and pasta. [I also loved the chicken liver toasts, which I ordered because the cibreo/chicken liver toast at Via Carota back home is one of my favorite things and my gut instinct, that they were distant kin, was correct. Gelato from Perché no! was essential on such a hot afternoon and was where my daughter discovered granita dolloped with cream, which is served with a straw. She then asked for it at every gelato shop for the rest of the trip.

We had dinner at Osteria Pepó, having, as per usual, not planned more than 12 hours ahead, but it was wonderful and they were so hospitable. I loved the carbonara and another pasta with truffle sauce, two things I never order back home where they always taste too heavy. In Italy, they’re perfect, as they should be.

Day 5: San Miniato

We went to the small market and walked around this adorable town in the morning, following recommendations from Emiko Davies helpful guide, then picked up groceries to make lunch at home. We languished in the pool that afternoon, had a not-worth-mentioning dinner near our house, and then some restorative Ma Ke Gelato.

Day 6: Forte dei Marmi and Pisa

We headed to the beach for part of the day, reserving chairs and umbrellas the night before at Bagno comunale Ponente “Le Dune del Forte,” which was less expensive than many others in the area. We had lunch at their cafe first which everyone agreed was one of our favorites of the trip — unfussy but perfect. I had the linguine alle vongole and an espresso granita and decided to never leave Italy.

We got gas on the way back from the beach and I have a tremendous number of questions about the full bar at the gas station, including espresso (in real cups with saucers, naturally). There was also what could only be described as a keg of Nutella with a pump on top; it’s all over for me if my kids find out those are available.

Every child wanted to see the Leaning Tower of Pisa, so we adults spent a lot of time Googling “Can you Tower of Pisa in 30 minutes? 15?” From experience I will say if you’re looking for a very quick in and out and photos, give it an hour total (we parked in a lot a couple blocks away), but also it’s quite stunning and I’m glad we saw it.

We had dinner from a restaurant we saw mentioned on Emiko’s website, Osteria di Golpaja. It was gorgeous and the food was great.

Day 7: San Gimignano

We went back to San Gimignano for a few more hours the next morning, plus more Gelato Dondoli. [We may or may not have promised the kids a two-gelato day.] After an afternoon of pool time, we had a gorgeous dinner outside La Locanda del Gobbo Nero. It was very kid-friendly; we liked some dishes (the eggplant parm in particular and a buttery truffle pasta) and others less so but had a nice evening with a great view.

Day 8: Siena

We spent the late afternoon in Siena. The duomo is gorgeous and I’ll make sure to tour it next time. We ducked inside for aperol spitzes and snacks when it rained, and then had a fancy dinner at the cozy La Taverna di San Giuseppe, which is lovely and probably our fanciest meal of the trip.

Day 9: Headed to Emilia-Romagna

We said goodbye to our house and stopped at Italiano Pasticceria Scarselli for pastries along the way, some of my favorites of the trip and possibly ever. Flaky turnovers with cream and almond (still warm), little sandwiches with prosciutto, and my current obsession, frozen coffee from an Illycrema machine, which I will make it my life’s mission to convince coffee shops in the US to install. [That and Zumex machines, please.]

We stopped at the popular Mò Mortadella Lab for sandwiches for lunch, and it is not even a tiny bit overhyped. We loved every bite. We walked around Bologna for the afternoon, got gelato from Cremeria Cavour, and had dinner later at Antica Trattoria. We loved the lasagna bolognese. We stayed at the AC Hotel Bologna for two nights.

Day 10: Parma

You cannot go to Emilia-Romagna- without learning about Parmigiano-Reggiano, Prosciutto di Parma, and Balsamic Vinegar of Modena (Aceto Balsamico di Modena) but were daunted by trying to arrange all three experiences separately. Enter: food tour guides! I reached out to Elizabeth Minchilli, who put me in touch with Alice Rossi, who put me in touch with Angelo Fanzini, who was absolutely wonderful; you must reach out to him if you want to do the same. We met in the morning at the Specialità la Traversetolese parmesan maker and got to see every step of the process up close, and of course, try all the things. Next we visited Piazza Peppino Prosciutti and got to see every part of the aging process while plotting to sneak one in our suitcase (kidding!). When we joked we couldn’t finish the last two slices of prosciutto, we learned the term “the shame” (la vergogna), which is not, for once, about eating richly but about wasting food. Italy, I love you.

We had an unbelievably excellent lunch at Agriturismo Al Vigneto, a favorite lunch of the whole trip. I’ll dream about the chef’s summer take on tortellini en brodo, made with little eggplant ravioli in a tomato water-like broth, forever.

Our final stop was Tenuta Medici Ermete, where we learned about their balsamic vinegar and the aging process, and tried them from thin and more acidic to thick like honey and sweet.

Later we ditched our kids and went out for drinks and snacks after a few failed destinations, at Tigelle & Vino. Tigelle (also known as crescentine) are small bread rounds popular in Bologna, and they were served warm in a basket along with fillings of our choice, allowing us to make quick, small, perfect sandwiches. We had gelato at Gianni. where I am now obsessed with the ricotta and chocolate chip semifreddo. My kids are going to be livid when they hear we had gelato without them, so please don’t tell them.

Day 11: To Venice

We got sandwiches to-go at Salumeria Simoni. The whole area is full of food and specialty shops — heaven but I didn’t want to buy too much before having our belongings heaved onto a boat. We dropped off our rental car and took a water taxi (the stand is right across the street from where most rental cars are dropped) to the gorgeous JW Marriott Venice Resort & Spa, on its own island. We took the hotel’s transport boat back to Venice later and walked around for a bit. I was last in Venice in the first three days of this millennium, when it was empty and cold and we had about $20 to spend each day. Needless to say, it’s a little different in August but we knew to spend as little time in the most crowded parts as possible. There’s so much more to see. I fell head-over-heels in love with Venice and am already plotting a return trip.

We had a great dinner at the cozy Osteria alla Frasca, followed by Gelateria Suso. I did not get the halvah but regretted it, even though my cherry cheesecake and salty pistachio were worth the wait in line.

Day 12: Venice

We spent a few hours at the hotel pool. Later, at the lobby bar, we ordered a limoncello spritz, only to be told by the waiter that he prefers the less bitter citrus liqueur called Italicus, and now we do too. We’re definitely tracking down a bottle now that we’re back in NYC.

Once back in the main part of Venice, we grabbed the kids some cookies from Pasticherria Marchini, because it was there and they were absolutely over the walking, but the cookies were great. It didn’t help that their tour guide (me), didn’t pay attention to the map when looking for Olbi Paolo, a bookbinder who is known as the keeper of centuries-old Venetian bookbinding tradition I cannot read enough about, and ran out of time to get there.

We instead pivoted to L’Isola di Pinocchio, which was one of the most special experiences on this whole trip. Please read more about Roberto and his shop online; there’s too much to fit here. I had been told he was “the sweetest man” and “basically Gepetto” and I was, in fact, undersold. He showed my kids his shop, which includes a swing that takes you from the earth to the moon, and couldn’t have been more of a pleasure to meet.

We had dinner at the highly-recommended by almost everyone I spoke to La Zucca, which is not vegetarian but very vegetable-centric. We loved the lasagnas.

Day 13: Venice

For our last day in Venice, and in Italy, we were very torn about whether we wanted to go Murano to watch glass-blowing, Burano, to learn about lace-making and linen, but in the end let our very tired children (Venice is a 10K+ step a day town, many little stairs for bridges, and they’d been troopers) guide us: a morning at the pool with french fries and gelato, and then a promise of a gondola ride (touristy, yes, but I’m also only planning on taking them to Venice once so we might as well “do it all”). First, however, I dragged everyone to the Gianni Basso Stampatore, only to find him (understandably) closed for most of August.

A family we’d met on our balsamic tour told us they’d hired a photographer in Venice to take family pictures, and we — people who never, ever remember to take family photos and are harassed by friends and family for never sending out photo holiday cards, lol — decided it was now or never. By the time we were done, there were no gondolas free anywhere (sorry kids) and we headed instead straight to dinner at Al Vecio Forno, a favorite in Venice of the trip, with a seafood-heavy menu and casual, friendly atmosphere.

Day 14: Back to NYC

“Your ride to the airport is here,” when that ride is a boat, is definitely a fun thing you can only hear in Venice. It was my husband’s birthday and when we went to board our flight, the Delta gate agents surprised him (no, nobody told them) with a personalized birthday card and a gift — a box of cookies from Burano — plus cheering. It was so sweet and a very nice way to treat even those of us in steerage class. [Yes we watched Titanic on the way home; can you tell?]