Italy Was Great, So Why Did I Come Home Craving a Do-Over?

I’m fresh off two weeks in Rome and Lucca with my husband, two little kids, and in-laws. I came back with a few treasures crammed in my carry-on, fresh style inspiration, and lots of musings on why this experience lacked the sense of ease and adventure of our other recent travels.

Last summer we visited Munich and the Bavarian Alps, and the year before that we stayed in Copenhagen. This year, the grandparents asked if we could all go to Italy. I’d had a longtime fantasy about spending a couple of weeks in a small town or two, living like an Italian family. But this was a once-in-a-lifetime trip for them, and they understandably wanted to get in all the highlights: Rome, Pisa, Florence.

I underestimated how high-pressure the sightseeing would be (even with a relatively short, flexible list of must-sees): setting alarms to book tickets, coordinating timed entries, and waiting in long lines. Everyone warned me it would be busy, but it wasn’t until I was milling against thousands of other hot bodies in the Colosseum with a toddler on my hip and Rick Steves playing in one earbud while trying to keep sight of my 6-year-old that this reality hit home.

The hardest part? As the designated planner, I felt responsible for making sure the experience was living up to everyone’s expectations. I took any complaints (the heat! the walking!) or lack of enthusiasm personally (yes, the pizza tastes different, but we have a plate of to-die-for melon and prosciutto on a dreamy Tuscan plaza!). I had trouble tuning it out and tapping into the sense of wonder and possibility that I count on travel to deliver.

While we’ve done home exchanges the past couple of years, we weren’t able to confirm one this time around. Home swapping is my preferred way to travel because it makes the stay feel more authentic and immersive, like trying on another family’s life. And in seven of the nine places we’ve stayed so far, the exchange homes have been more luxurious and convenient than the rentals in our budget.

I also missed cooking some of our own meals. I find pleasure in the novelty of perusing a foreign grocery store and finding my way around a sophisticated stranger’s kitchen. Sitting down to a simple meal at home, ideally on a patio, has been a way for us to wind down and connect after an active day.

This trip reminded me how I like to balance time in cities (I thrive on urban energy!) with quieter settings close to nature. One of my top days in Italy was riding the train for an hour to the town of Bracciano to tour a magnificent, remarkably well-preserved (and empty) 15th-century castle that overlooked a blue lake, where we swam afterward.

Another afternoon we settled in at a beach club in Viareggio on the Italian Riviera, where I splashed with my oldest in the gentle and clear Mediterranean waves, with the snow-capped Apuan Alps in the background. Driving into Garfagnana, a mountainous corner of northern Tuscany, where we stopped to wander around hilltop towns and walk across a medieval bridge of diabolic proportions, was the perfect antidote to the grit and clamor of Rome.

When I’m in the planning phase, I have to keep reminding myself that my most satisfying trips are less about doing it all (I just get so excited digging into a new guidebook) and more about marinating in the particular beauty and idiosyncrasies of a place.

As I organize our family itineraries, I’m learning what makes my older daughter light up when we travel. For one, she loves climbing a tower. We counted the 551 steps up to St. Peter’s Dome and the 230 steps up the brick Torre Guinigi in Lucca, to a tiny rooftop garden with trees sprouting into the sky.

She also loves a show. On our way to see the ballet A Midsummer Night’s Dream at the Teatro dell’Opera di Roma, she skipped in anticipation. And even though the puppet show at humble Pinocchio Park was in Italian, its antics had her and her sister shrieking and giggling. She even sat through 60 minutes of opera in the gorgeous Church of San Giovanni in Lucca (Puccini’s hometown), though she got a little squirmy.

Other surefire hits for my 6-year-old:

• Biking (this time it was the whole family cycling the loop atop the fortified walls of Lucca on a four-wheeler)

• Beaches

• Playgrounds

• Train and bus rides

• Carousels (the vintage merry-go-round in Florence’s Piazza della Repubblica was a lifesaver)

• Ornate church interiors (though Italy tested her stamina for these)

I don’t know if we would have made it through all the long, hot days of walking without a daily gelato break (the cones got progressively bigger) and a promise of ravioli or pizza for the next meal.

My daughter doesn’t enjoy museums unless they’re geared toward kids, despite my coaxing with scavenger hunts and sketchpads and promises to visit the gift shop. But on this trip, I found that listening to an audio tour makes her feel grown up. This got us through a quick visit to the Galleria Uffizi, where she was excited to spot paintings by Michelangelo, who she studied in her kindergarten IB art unit. Now she’s displaying a postcard of the Holy Family on her dresser.

While I didn’t make it to the flea markets and vintage boutiques saved on my map (the reality of family travel!), I was able to sneak away for a few quick purchases for myself. (My kids came home with an impressive collection of pressed pennies for their treasure box — a perfect souvenir.)

1. A candle in a fruity marine scent from the ancient Florentine perfumery Farmaceutica di Santa Maria Novella

2. A silk scarf and a bluebird-colored men’s linen button down from a couple of humble thrift stores in Rome’s Monti neighborhood

3. A pair of artisan-made peep-toe mules*

4. A handmade straw pouch from a multi-generational workshop*

5. A (very reasonably priced) bronze pendant necklace inspired by ancient Rome at a jewweler’s tiny workshop in Testaccio*

6. A pair of pajama shorts from Schostal Originals for lounging and beach days*

*Thanks for the shopping recs, Gabriela R. Proietti! You can influence me any day.

Studying the outfits women were wearing around Italy was just the palate cleanser I needed from the digital algorithm. Before we left, I had a few items on my mental shopping list. But this desire to purchase dissipated while I was away. I was reminded that there are a thousand ways to be chic, and all the “must-have” items that will complete your wardrobe are a marketing illusion. I came home less interested in shopping links and more excited to lean into the power of scarves, brandless basket bags, and creative outfit styling.

In my wanderings from Pigneto to Parioli, I didn’t notice anyone (at least over the age of 18) wearing the following: graphic tees, track shorts, crew socks, jorts, wire glasses, barrel pants, ball caps, matching sets.

What I did see: sneakers, delicate sandals, Mary Janes, scarves used in a gazillion ways (even twisted around handbag straps!), straw bags, loose pants, midi (often silk) skirts.

I’ll end by leaving you with a motley list of highlights from our two weeks in Italy:

1. The playground at Piazza San Cosimato in Trastevere: lively, shady, plenty of seating, and right in the middle of the neighborhood action

2. Giardino degli Aranci, a park overlooking Rome, where the girls danced to a street musician and I bought a sexy watercolor that I plan to hang in my bathroom

3. Poste Vaticane. My kid got a kick out of choosing a postcard, writing a note to her grandma, and dropping it in the box at the Vatican post office.

4. All the €2 cappuccinos I enjoyed throughout the day, especially at the glamorous bars with friendly staff, like Caffè Gilli in Florence.

   

5. Walking up to restaurants as a party of 6 and immediately being seated at a prime alfresco table (I’m still thinking about the cacio e pepe at Naumachia Ristorante) or getting a dinner reservation at a nice restaurant with 24 hours’ notice. (Why can’t dining out be this easy in Southern California?)

6. Villa Torlonia, a peaceful park on the outskirts of Rome

7. Admiring how Italian women of all ages and shapes wear bikinis without any hint of the self-consciousness that plagues American women. They just carry themselves differently.

8. Pistachio everything: affogatos, crispy filled aragostina pastries at Sant’Eustachio Il Caffè, and the purest tasting gelato at cozy Il Picchio Gelateria Naturale

9. La Roche-Posay Anthelios UVmune 400 SPF (not available in the U.S.), which melts into skin and disappears on contact. I’m religious about sticking to mineral formulas but made an exception because European products adhere to stricter consumer regulations.

10. Bernini’s Apollo and Daphne at Villa Borghese

Up next week: Five ways I’m finding more simplicity and adventure at home this July.

How do your trip visions line up with reality?

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