A Life Well Traveled

I’ve been to Italy many times, and I can confidently say that I’m not done with it. The first trip was our honeymoon, when we did Rome, Sorrento, Positano, Capri, and Ravello. Years later, we went back with the kids and my parents, stayed in Tuscany, and eventually made our way back down to the Amalfi Coast.

That second trip made me realize there are places you can visit once and move on from but Italy is not one of them for me. There are places I would easily go back to tomorrow for the same restaurants, the same hotels, the same streets and the same coffee.

So no, this isn’t my list of the “best places in Italy.” I haven’t been everywhere but these are just the places that stuck with me enough that I’d plan another trip around them in a second.

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Lucca

Lucca was one of the best parts of our family trip to Italy and the main reason was how we did it. We went with our kids and my parents, which I would do again in a heartbeat.

Instead of staying in a hotel, we rented a villa in Lucca and it felt like something out of a storybook. In every corner there was another trinket, piece of art, and unexpected treasure. The whole place had so much history and personality that my dad and I were convinced we had lived there in another life.

There was something almost eerie about how familiar it felt and it felt like home. Everything in the villa was collected over time, like every detail had a story and every room had been lived in and loved.

Our host was incredible and made us feel like family. She arranged for a private chef, Francesca, who came to the villa for a cooking class one night and then returned to chef a private dinner the next night. It was one of the best meals we have ever eaten, and she was literally walking outside and picking herbs from the garden while she cooked.

Our host even arranged for an osteopath to come for massages one afternoon, and we spent the rest of the day around the pool, ate at the house and basically did nothing. I highly recommend doing nothing in Tuscany at least once in your lifetime. Twice if you’re lucky.

Because Tuscany is so spread out, we rented cars and it was definitely the right choice. Tuscany was surprisingly easy with kids because we had the freedom to drive where we needed to go whether it was Lucca, Forte de Marmi, Florence, or another village.

Lucca itself has everything I love in an Italian city: beautiful piazzas, churches, cobblestone streets and great restaurants, but without feeling overwhelming. Its Renaissance walls surround the historic center, and the top is now a wide, tree-lined promenade that makes the city feel so authentic, We ate so well here too but honestly, some of the best food of the entire trip was back at the villa, which was kind of the point.

Forte dei Marmi

One of the best parts about staying near Lucca was that we could have the whole Tuscan countryside experience and still get to the beach. Forte dei Marmi has a completely different vibe from the hill towns and olive groves people usually picture when they think of Tuscany. It’s very much celeb-central and is known for attracting some note-worthy people.

The luxury shopping is amazing, with beautiful boutiques, designer stores, Italian brands and gorgeous storefronts everywhere you turn. We did some damage in the Gucci store and bought authentic Italian leather bags and clothes that remind us of our time in Tuscany.

Italian beach clubs are just built differently. You show up, they set out your chairs and umbrella, you order a drink, have lunch, stay all day, and you never have to lug everything but the kitchen sink to the beach. In Forte dei Marmi, you can shop in the morning, head straight to the beach club, have a long lunch, and spend the rest of the afternoon doing absolutely nothing. That’s pretty much my ideal day.

It was such a fun contrast to Lucca: one day olive groves and a villa, the next luxury shopping and the sea. I wish we went back more but there was so little time and so much to see.

Sorrento

Sorrento was part of our honeymoon, so it will always have a little extra nostalgia for me. We stayed at the five-star, Bellevue Syrene, which is still one of the most beautiful hotels we have ever stayed in. It sits right on the cliffs overlooking the water, and you can go down through the cliff to the hotel’s private sea area. The views, rooms, service and food were all second to none.

We went to some amazing restaurants on that trip, including a few Michelin-starred meals but some of our favorite food spots were hidden along the cobblestone paths. One of my favorite experiences was our day at Villa Ida, a private family home that hosts cooking classes. We made fresh mozzarella, ravioli, zucchini flowers, and more and even saw the wine cellar where they make their own wine.

We also found Peppe & Italia, an incredible little boutique with beautiful shoes and menswear, which became a spot we still place orders even though we are back in the States. Sorrento is so easy to enjoy. Walking around, you’ll feel like a local grabbing a coffee, a croissant, or just moseying in and out of boutiques and cafes.

Positano

Positano feels like home to me. We went there on our honeymoon and then came back again with family and it’s one of the few places I’ve traveled where I never feel like I’m finished with it. Yes, it is popular. Yes, everyone has seen a million pictures of that cliffside view. And yes, there are tourists everywhere in summer, but I still love it.

We’ve stayed at the 4-star, family-owned Hotel Poseidon, which I will recommend over and over again. If you haven’t stayed there, you should. It is elegant, warm, and quintessential Positano. The terrace views are unlike anything I have ever seens and Il Tridente, the hotel’s famous restaurant, is one that we’ve returned to time and time again.

Also, read One Italian Summer before you go. Trust me.

On another trip, we rented a villa built into the cliff. It was gorgeous, with a full kitchen, beautiful interiors and ridiculous views, but the only catch was about 100 steps.

Which brings me to Positano with kids. Everyone assumes it is impossible with a stroller, but I actually found the main part of the town to be accessible. You do need to choose where you stay carefully because something that looks five minutes away on a map might involve an actual mountain climb, but once you are on the main pedestrian streets, it is very doable. You just move slower, which honestly is not a bad thing in Positano.

There is so much I love here: the coffee, gnocchi alla Sorrentina, ceramic shops I cannot walk past without going in, linen, handmade leather sandals, little boutiques, the people and, obviously, the food.

One of our favorite experiences was a cooking class at Il Ritrovo in Montepertuso, way up above Positano. They pick you up and drive you up the mountain and if cliffside driving makes you nervous, hold your breath. But once you get there, you’ll realize it was worth it.

The food was some of the best we had in Positano and the woman who owned the restaurant treated us like family. She was our nonna for the day and helped us cook up some of the Positano’s most popular dishes. We even found out that her niece and nephew own an Italian restaurant and pizzeria that we go to back home. Those are the meals that not always the fanciest place or the hardest reservation, but the places where nonna puts another plate in front of you because obviously you haven’t eaten enough.

There are plenty of great restaurants around Positano, including Il Tridente and the restaurants at Le Sirenuse, but I also have very strong opinions about the beach clubs. Don’t automatically go to the main beach just because it is the one you recognize from Instagram. The best Positano beach clubs are worth the hike. Trust me, you’ll feel like a local. Those spots deserve their own article. Stay tuned.

Positano is also where one of my favorite movies, Only You, was filmed, which probably did not help my obsession. I just love being there, grabbing coffee, walking down the hill, shopping, going to the beach, eating all the pasta, and doing it again tomorrow.

Rome

Rome is probably my biggest travel regret in Italy, not because I didn’t like it, but because I don’t think I realized how much I liked it until we left. We went on our honeymoon and there was so much to see that I think I spent most of the time trying to hit every spot in instead of appreciating where we were.

It is almost overwhelming. You spend your whole life seeing pictures of the Colosseum, the Pantheon and ancient Roman ruins, and then suddenly you are standing in front of them.

We stayed at J.K. Place Roma, and it was unmatched. Definitely more of an adults’ hotel and perfect for a honeymoon, the interiors were gorgeous, the service was incredible, a true quiet luxury spot.

And obviously, Rome was about the food too: cacio e pepe, artichokes, pasta, pizza, coffee and more pasta. One meal basically became a mission for me. Anthony Bourdain had eaten cacio e pepe at a restaurant in Rome without really revealing where it was, and this was long before you could open TikTok and figure something out in six seconds. I spent months researching and trying to find it, and eventually I did: Roma Sparita.

And yes, the cacio e pepe lived up to the hype.

The biggest thing I would change about Rome would be to stay longer. Rome needs time. You absolutely need to see the big sights but I wish we had also given ourselves more time to wander around. We packed too much into too little time, and I didn’t fully appreciate how amazing it was until we left.

Now that our kids are getting older, I cannot wait to bring them. They would lose their minds over ancient Rome and I think going back with them will make us experience the city differently anyway: slower, more curious, and probably with a lot more conversations about gladiators.

The Places I’d Choose Again

There are still plenty of places in Italy I haven’t seen. And at the same time, I don’t think every trip needs to be a repeat of the last one. But I’ve also never understood the obsession with always chasing somewhere new. Sometimes a place becomes part of who you are. You know there are a hundred other Insta-worthy spots you could go to, yet you still find yourself thinking about the same ones.

For me, it’s the villa in Lucca that felt strangely familiar. It’s Forte dei Marmi, where everyone and everything is so chic. It’s a hotel built into the cliffs in Sorrento, the streets of Positano I’d happily walk up and down for the hundredth time pushing a stroller, and a plate of cacio e pepe in Rome that took me months to track down and about five minutes to finish.

That’s the stuff that sticks with me. Not how many places we managed to check of but the ones that were hard to leave.

Those are the places I’d go back to.