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The Anti-Optimization Guide to Rome

To prepare for a trip to Rome, you must prepare your psyche more than you do your suitcase.

As a food and travel writer, I am less interested in treating a travel itinerary like a laundry-list roster. The key to a meaningful and fulfilling trip is to leave room for surprise and spontaneity. In fact, research shows novelty slows down the perception of time and consolidates memories.

So for the sake of remembering stories for future loved ones (I picture myself as the fun aunt), my approach to a trip is to plan a few pillar places or experiences, then let curiosity nudge me the rest of the way.

This is a philosophy especially relevant in Rome, where rushing and rigidity are cardinal sins. To prepare for the city with rigidity would be antithetical to its spirit. Instead, I primed my psyche with art — the kind that’ll shift me into a disposition that matches that of the city: romantic, fluid, mystical.

I read Easy Beauty by Chloé Cooper Jones and made a playlist called Forever Roma. I dined at Frankie’s in Carroll Gardens and listened to this podcast about how Ancient Romans perceived sex.

This is Rome to me.

Nothing practical. All mystical, all want.

A solo trip to Rome does not require much of a ‘what to pack’ or ‘where to book’ interrogation, but rather a reckoning of what to feel.

So, what did I want to feel when I visited Rome alone for my second time?

Free.

I wanted to feel limitless. I wanted to feel light in my body, buoyant even — a small task for a mighty city. I wanted to feel connected. I’ve found the way to do that is to make myself uncomfortable for just two seconds by introducing myself to a local, then allowing those two seconds of discomfort to turn into two hours of pleasant conversation.

I also wanted to feel slow, as opposed to my usual inclination toward over-stimulation. Gratified and full, but not engorged. I wanted to be near sensory pleasure at all times, minus the hedonism.

Throughout my eleven days in Rome, I ended up feeling all of that — sometimes in the passenger seat of a vintage Alfa Romeo (surprise itinerary item!), sometimes under misty skies on a long run (novelty!), and sometimes in the warm buzz of Sardinian wine in a Sicilian’s home (memory making!).

If you’re interested in feeling any of the above, this is your guide to Rome.

In the age of recommendations and optimization, it’s hard not to succumb to the pressure of sucking every last lick of juice, every last bite of pulp from every fruit of opportunity. Tiktok makes sure you don’t miss any last thing.

I’d suggest treating this list more like a slow burn, where one single plan can unfold into an experience, or multiple experiences, that you couldn’t have ever planned for.

Pick a few pillars from below, start there, and let the city’s friendly, flirty spirit turn you toward the world.

14 Roman pillars to get you started:

1. Enjoy a long, slow lunch at Il Giardino, at Hotel Eden, and make sure Francesco pours you his favorite wine.

I am convinced Il Giardino has the best terrace view in all of Rome, particularly from the inside of the restaurant. This rooftop restaurant is on the tippy top of Hotel Eden, which is just above the Spanish steps. The walls of the restaurant are nearly all windows flaunting a different angle of Rome, each shedding sunlight onto the plates of fresh pasta and shimmering glasses of local wine.

I recommend doing a three-course lunch and having Francesco guide the way with his favorite wine pairings. He has been at this hotel for 35 years, so it will be hard not to invite him to sit down and tell a story or two.

2. Run early in the morning along the River Tiber on the wide riverside paths. Then, finish with an espresso and banana bread from Forno Monteforte.

Rome is an open-air museum with beauty etched into each corner, so long as you don’t forget to look up. Looking up can be difficult while running along the cobblestone streets of this ancient city, but it’s worth it. I ran the Wizz Air Rome Half Marathon while I was there, and my favorite stretch of the course was the Lungotevere, the riverside roads along the Tiber that head toward Castel Sant’Angelo.

To conclude my run, I went to Monteforte cafe. Then went again at least six more times.

3. Visit Pierluigi for dinner and order more seafood than you think you should.

Ah, Pierluigi! Alive, bustling, sexy, loooong and drawn out. The way I found myself at Pierluigi was cinematic. I was hoping to dine solo for lunch, but I had just missed the 3:00 pm cutoff. Sad for me, except that a photographer shooting pictures at the restaurant saw that exchange, and invited me for a drink later on, as well as dinner once again at Pierluigi with a crew of his friends.

My answer was yes. Duh.

That night, I sat at a table of Italians, finding shared worlds in the restaurant industry. Get the fish — all of it really. Ask your server to send their favorites, or the chef’s. Trust it.

4. Vintage shop at Ciao Vintage, Mercantile Vintage, or Humana Vintage. Or the Porta Portese Flea Market if you’re there on a Sunday.

Rome has an underrated vintage shopping scene, and I highly suggest spending a few hours strolling along Via del Pellegrino, right off Campo de’ Fiori, for a mix of clothing boutiques and old bike shops. I also love shopping at Chez Dede for eclectic boutique gifts.Via Panisperna in Monti is a great starting point as well.

5. Get a ciambella, cornetto, and cappuccino from Caffe Trastevere.

Stand right at the bar — as the locals do — and listen to the gorgeous exchange of grazie, prego, boungiorno, etc. Watch the old couple smoke a cigarette and read the paper. Savor the ciambella di mele with a frothy cappuccino.

6. Meet Daniele from Trattoria Da Lucia in Trastevere, who knows true hospitality.

A local tailor introduced me to Da Lucia. I told the tailor I had an idea in mind for dinner, and he said, no. My eyebrows scrunched, offended.

He said “I have a different place I want to take you.”

We arrived at Da Lucia where Daniele greeted us swiftly and ran the front-of-house with precision and a bit of Italian chaos. I just loved it. It’s a tiny, quaint spot in Trastevere, where I saw no Americans. Daniele started bringing out plates of prawns (you must always order prawns!), artichoke, sea bream carpaccio, and a decadent clam pasta. Sit outside, get the flan for dessert, ask Daniele his favorites, take four hours.

7. Party with a Peroni and a mix of tourists and locals at Bar San Calisto.

If you’re looking to meet some friends and make some trouble, Bar San Calisto is an iconic spot that brings all nationalities together. The crowd spills out into the piazza where they share Peronis and cigarettes. Make a few friends, even if it’s only for the night.

8. Watch the sunset at Cielo Bar at Hotel de La Ville.

Cielo Bar is a chic, dreamy bar with a nightly DJ on the rooftop of Hotel De La Ville. They have a “Diva Martini” which is always a good sign. Their riff on a negroni, with Italian Punt e Mes and cedar essence, pairs nicely with the sunset. I recommend a date night here.

cielo bar

9. Find someone — a friend, a lover — to take you on a Vespa to the Borghese Gardens.

Strolling through Borghese Gardens early in the morning or right before the sun goes down is poetic. It’s best if you arrive by Vespa, but you will be forgiven if that doesn’t work out. Right at the edge of the gardens, the view of the entire city is expansive and prime for a photoshoot. Vendors sell lots of Aperol Spritzes there too, which is not a bad idea.

10. Sip a negroni and make a friend at Bar della Musa. If you can, stay the night at the hotel.

I made two Irish friends sitting at the bar at Bar Della Musa, tucked inside Palazzo Talìa. This hotel was designed by the director of Call Me By Your Name. The hotel is a 16th-century palazzo that used to house cardinals, clergy, and was once even a school. It’s been converted into an ethereal 26-room hotel with a mirror-lined bar that is quite the scene.

il bar della musa at palazzo talia

11. Try a supplì from Casa del Supplì or Supplizio.

These fried risotto balls are a classic Roman street food. There are a lot of tiny cafes that churn out supplì and natural wines.

12. Roam Galleria Spada while you listen to Forever Roma.

Solo strolling through a less-crowded art museum is nearing ecstasy. When I walk through museums, I like to ask myself: Why am I drawn to this piece? What piece of art reflects my internal state right now? What piece of art reflects where I want to be?

galleria spada

13. Practice your Italian at a solo lunch at Trattoria Da Teo.

A lunch at a timeless Italian trattoria that hasn’t yet been overrun by tourists is a perfect opportunity to practice speaking Italian.

“Un tavolo per una persona, per favore,” I said timidly.

I ordered the carbonara, a Campari spritz, a plate of prosciutto, then watched the Italian businessmen chat about anything but business at the tables around me.

14. Order the pistachio ice cream from Gigi Rigolatto at Orient Express La Minerva.

The meal I had at Gigi’s — the rooftop restaurant at Orient Express La Minerva — was a portal, serving up classic but refined Italian cuisine. I still dream of the succulent prawn carpaccio (How can a carpaccio be succulent? Well, it can). The tagliolini with langoustine tartare was substantial and chewy, balanced with warmth and brine. But, please, please, don’t miss the pistachio ice cream, which is a gargantuan swirl doused in olive oil, salt, and fresh crunches of pistachios.

gigi’s pistachio gelato

Eat well, drink well, take more time than you think. Enjoy Rome.

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