When a Longtime Backpacker Goes on a Luxury Cruise

Returning to Italy 17 years later: Notes on style and nostalgia

Sunsets came fast, around 4pm. I slept in cold hostel dorms for about €20 a night and subsisted mostly on sandwiches and gelato. I wandered around quiet and eerie streets for days on end, getting lost (I wouldn’t get a smartphone for two years) as fog rose from dark canals. I learned that a gondola ride cost €80, which seemed like $1,000 to me then.

It was December 2008, and I’d just graduated with a journalism degree into the throes of the Great Recession. So I answered an ad for an au pair job in Barcelona. My employers were visiting family for a month, and I took the opportunity to see Italy, beginning in Venice.

I watched extended families dressed up for the evening passeggiata as they paraded down main thoroughfares and spotted a glowing window where a family celebrated shabbat. I was so lonely yet overcome by the beauty of it all.

I took this snapshot with an actual digital camera.

Fast forward 17 years to last week, when I found myself back in Italy under entirely different circumstances. I was with my husband, having scored a last-minute invite to a coveted company cruise.

This time, I only had a few hours in Venice, and we splurged on the gondola. Those 45 minutes felt surreal.

Here are a few other highlights from our whirlwind tour, along with action shots of some outfits I packed in my carry-on.

In Rome at the Fontana delle Tartarughe (Turtle Fountain), where I remember taking a grainy photo in 2008.

An Evening and a Morning in Rome

After dropping our bags at our assigned hotel by the airport and changing in the gym bathroom, we took a taxi to the Colosseum. We walked around in a daze, stopping for a pistachio affogato and then strolling past the Trevi Fountain and the Pantheon on our way to Trastevere, the meeting point for the food tour I’d signed us up for a couple of days prior.

City parks are one of my life’s pleasures.

In the morning, we called another taxi to take us to Piazza del Popolo. I had a cappuccino, and we climbed the Spanish Steps up to the gorgeous Villa Borghese park (all the kids on roller skates made me excited to return with my girls) and ordered paninis on a long walk around Rome’s “Upper East Side,” Parioli.

I consume everything by Elena Ferrante, author of the Neapolitan Novels.

A Day in Naples

On my last trip to Italy at age 23, I took the train to Naples for one thrilling day. The city was dealing with a garbage crisis and scary mafia drama. I was too nervous to even carry a purse, instead stashing my ID, Nokia, a few euros, and some torn-out guidebook pages deep in a pocket of my heavy coat. I explored a magnificent archaeological museum decorated with cobwebs, ordered the Eat-Pray-Love pizza, and ventured about two blocks into the Spanish Quarter before getting spooked.

I’m making my way through Gabriela’s entire Local Style archive as “research” before our upcoming family trip to Italy (planned long before the cruise invite).

This time around, we started with a walking tour (Galleria Umberto blew my mind, again), and when that wrapped up early, the first thing I did was pull up Gabriela R. Proietti’s guide to her adopted hometown. (We’d already sprinted off the ship first thing that morning to grab an espresso and pastry at Augustus Napoli based on her recommendation.)

We ventured deep in the Centro Storico, taking in all the hanging laundry, graffiti, lawless motorbikes, and altars, and stopping at Caffè Mastracchio for caffè caldo freddo (sort of like an affogato).

Wearing the skirt I bought at Retrophilia in Naples to dinner on the ship.

Then we found a few moments of peace in a somewhat hidden courtyard at the Cloister of Santa Chiara before finding Retrophilia, where I bought a fun silky pleated skirt from Luigi (and am still regretting not buying his handmade silver Mary Janes).

Gabriela’s artful stack inspired my necklace selection at Salvio Gioielleria. (Image courtesy Local Style)

On our way back to the port, we swung by Salvio Gioielleria, where I picked out a couple of colorful necklaces, which I’m already wearing on repeat to add some flair to my San Diego outfits.

I pre-booked the Dubrovnik Pass, which gave us access to the city walls and several other sites in the Old Town.

A Day in Dubrovnik

We got an early start to walk the city walls, which felt like entering a fairy tale (fitting, as I was reading the novel Lady Tremaine).

Probably my favorite vacation outfit

Next we did a self-guided tour of the pristine old town (I picked up a table runner with traditional Croatian embroidery and a cute print at a market stall along the way) before catching a ride to the nearby resort town of Cavtat.

I joined the sunbathers on the rocks by Beach Bar Little Star in Cavtat.

We walked along a shady seafront promenade to a secluded beach bar, where I indulged in an Aperol spritz and dipped my toes in the Mediterranean.

The Sea Organ in Zadar creates the most atmospheric soundtrack.

A Day in Zadar

We started with a guided hike in Paklenica National Park (45 minutes by car), which turned out to be a climber’s paradise and a nice reprieve from all the city-hopping. In the afternoon, we sat down for lunch at Bistro Pjat (I ordered the cuttlefish on a recommendation, mind over matter) before strolling around the old town, exploring a park built atop the city walls, and listening to the haunting notes of the Sea Organ on the breezy waterfront. I noticed (here and in Dubrovnik) all the groups of kids running around town unsupervised after school, hoping that one day that level of freedom would be acceptable in our California neighborhood.

Venice really looks different from down in the canals.

An Early Morning in Venice

The official trip agenda had us disembarking at an isolated, industrial port and transiting straight to the Venice airport for our 1:30pm flight, but I couldn’t fathom being so close to the city without seeing it. I convinced my husband (and boy, did it take some convincing) to sneak off the ship early. We found a cab to take us to Piazzale Roma, where we found a luggage storage operation. And then we were winding our way along the Venetian streets and bridges to Piazza San Marco before 8am. A thrilling success!

En route, we ducked into an elegant, standing-room-only cafe that looked like it hadn’t changed in about 100 years, queuing behind the locals for an espresso and pistachio cornetto (a fellow patron corrected my pronunciation, demonstrating a “k” sound in pistakio).

After our gondola splurge, we hustled back for our luggage and caught a shared bus to the airport at 11am, because I’m still a bit of a backpacker at heart.

She would fit right in on the Roman streets. (Image via Pinterest)

First Impressions: Spring Style in Rome

While my time in the Italian capital was brief, I took careful mental notes on the outfits I saw on the streets. One of my favorite things about European style is that no one’s worrying about looking like they’re “trying too hard” when they get dressed.

Here are my initial observations on what Italian women (and all the visitors from around Europe) are wearing right now.

Footwear: ALL the ladies were wearing sneakers, mostly low-profile styles by Adidas or Veja, but chunkier New Balance types were also still going strong. I saw a couple loafers, and some boots came out at night, but I was an anomaly in my sandals, though that might change come summer. (Sneakers just wouldn’t work with all the barrel-leg bottoms in my suitcase.)

Outerwear: Jackets were mostly tailored and often cropped. In the evening, I saw countless leather jackets (I fit right in) and some trenches. Blazers were common, both day and night. (Blazers are one of the things I miss most about the corporate world, but I can’t for the life of me figure out how to wear them in San Diego without looking like I’m going to a business lunch.)

Bottoms: I observed mostly wide-legged or otherwise loose pants, cropped or full length, and the occasional skirt.

Accessories: Designer sunglasses and bags punctuated many of the outfits. The latter were often structured leather and worn crossbody, though shoulder bags were also common. I also took note of some softer, crescent-shaped crossbody bags that would work well for my cargo-bike-mom life. Finally, there were plenty of scarves worn in every way imaginable. Europeans are just so chic!

xx Rachel

Up next week: Everything on my summer mom bucket list — pool days, skorts, camping trips, and more.

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