Italy: A Last-Minute Workation Getaway
- Shauna Leff
- Aug 3
- 7 min read
Florence
Italy is one of the most visited countries in the world—welcoming over 60 million international tourists annually. And this summer, it felt like everyone was following in the footsteps of Jeff Bezos and Lauren Sánchez to Venice. That said, my husband and I had long planned to take our annual trip while our kids were away at summer camp. We had a few ideas of where we wanted to go this year, but in all honesty, Italy was not on the list.
Since we both work remotely, we started calling these breaks “workations”—working during the day, then soaking up a new culture (and great food) after 9 PM, sparingly taking a day off or two. These trips for us are not about checking off cities or seeing every site. It’s about carving out space—away from our routines, away from deadlines—to reconnect. To walk and talk. To sit down to a late dinner with a glass of wine and talk about life. To hear different accents, admire centuries-old architecture, and remember what it's like to just be together.
This summer, we only had a week to play with, and there was one complication: I was in Florida helping a family member and didn’t have my passport with me. I needed to find a flight route where we could meet up during a layover and still return in time to pick up our son from camp in Asheville, NC—a regional airport with limited options. Another key criteria? Using airline miles. I found flights to Rome for just $75 each using miles, and within less than 24 hours, we were airborne—with no other plans in place.
Italy, Redux
The last time I visited Italy, I was 21, kicking off a backpacking trip. I hated Rome. I vowed never to return—at least not until I was married. (Spoiler: I kept that promise.)
I remember loving Venice and being excited to see the Leaning Tower of Pisa—probably because I grew up watching Superman as a kid. But Spain and Switzerland won over my heart on that European backpacking trip and Italy has been far out of my mind. It doesn’t help my pictures from that trip are buried in some album in my parents’ attic. So, as they say, out of sight, out of mind.
Fast forward 25+ years: I found myself on a plane to Italy with no hotel booked and no itinerary. Thankfully, in-flight Wi-Fi saved the day. Because the trip was so last-minute—and knowing most people plan their Italy vacations months in advance—I found most travel guides overwhelming. Add to that: my husband had meetings to take in the middle of the day, so we needed a central location, reliable Wi-Fi and a relatively simple plan. To keep it easy, we decided to split our time between Florence and Rome.
Florence
After landing in Rome early on a Sunday morning, we bought train tickets at the airport and arrived in Florence two hours later. On the flight, I found a last-minute one-bedroom Airbnb in the heart of the city. The location was perfect, and the price even better. (Pro tip: You can sometimes score great deals on Airbnbs when booking same day.) With most places closed midday on Sunday, we spent the afternoon strolling, snacking, and settling in.
Florence is a walking museum. Every street has a story, every corner a photo op. We didn’t feel pressured to visit every museum or church. Instead, we let the city guide us—exploring piazzas, sipping wine, and following our noses to incredible meals.
I used Apple Maps to create a personal restaurant guide, prioritizing spots recommended by locals—not just tourists. (Heads up: reservations are a must for some restaurants. One restaurant we really wanted was fully booked for the entire week. We were told people book out weeks in advance).
Same goes for museums: if you want to visit the Uffizi or Accademia, book ahead. Since our trip was so last-minute, we embraced the “wander and discover” model.
Highlights included:
Mercato Centrale – A bustling food hall perfect for lunch
Museo Galileo – My husband’s top pick, and a surprisingly fascinating museum
Giardino Bardini – Gorgeous views and a peaceful escape from the crowds
Stumbling through piazzas lit by golden-hour sun
Rome
We wrapped up our trip with a few days in Rome, staying in a central spot near the Spanish Steps, surrounded by some of the best shopping. Again, a last-minute Airbnb deal worked in our favor.
Rome is big, but we walked everywhere – getting in 10+ miles a day without even trying. The city’s energy, history, and gelato are all worth the hype.
Highlights included:
Galleria Nazionale d’Arte Moderna – Stunning and often overlooked
Villa Borghese – A scenic park perfect for a morning stroll. You can rent row boats and go out in their little lake which reminded us of what you may find in Parque Chapultepec in Mexico City.
Campo de’ Fiori – A lively market square
Trevi Fountain, Pantheon, Piazza Navona, Jewish Quarter, and of course, the Colosseum – All iconic, all worth seeing (even if only from the outside)
Gelato vs. Granita
Italy is world-famous for its gelato—and yes, it’s every bit as good as they say. In both Florence and Rome, you’ll find at least two or three gelaterias on every block, each one seemingly trying to outdo the next with elaborate displays, towering cones, and flavors that tempt you from the sidewalk.
But here’s the twist: I’m a granita girl. Granita is Italy’s answer to the slushy—cool, light, and refreshing. It typically comes in lemon, mint, orange, or coffee, though higher-end shops offer flavors like pomegranate, blackberry, coconut, or strawberry. In the heat of summer (it was in the upper 90s every day we were there), granita hit the spot in a way gelato sometimes didn’t.
Some granitas are made fresh and spooned into cups with a texture like shaved ice; others are churned in machines like slushies. If you love a citrusy frozen lemonade, this is your treat.
One of my favorites was at Giolitti in Rome, a 120-year-old café with original 1940s decor, a wraparound marble bar, and an old-school Italian charm that feels cinematic. Another highlight was a lemon-themed franchise we kept spotting around Rome called Limone, which served everything from lemon gelato to fresh lemonade to—you guessed it—lemon granita.
My advice? Try both. Then decide where your loyalty lies.
Romancing Restaurants
There’s no shortage of restaurant guides and foodie blogs for Italy—and yes, they can be helpful. But part of the charm of eating in Italy is not planning every meal. Some of our favorite dining moments weren’t in the guidebooks or saved on a Google Map—they were spontaneous discoveries tucked down alleyways or nestled on quiet piazzas.
Whether it was a quick Italian breakfast (coffee, juice, and a croissant), a slow aperitivo in the early evening, or a dinner that lingered well past 10 PM, we followed our instincts—and our stomachs.
Of course, we also follow a few simple rules when we travel to avoid obvious tourist traps:
Avoid places where someone tries to lure you in from the street
Skip menus with photos
Look for regional authenticity
Check reviews—especially if there’s no one inside
Long lines? We usually do a quick search to see if they’re worth it. One spot in Rome, Osteria da Fortunata, came highly recommended by friends who had just returned, so we made time to go and wait. We weren’t in a rush, having already enjoyed an aperitivo (wine and a meat-and-cheese board) in a different neighborhood earlier that evening, so the wait felt more like part of the experience than a hassle.
My friend Claudio insisted we try the gnocchi alla Sorrentina, and he was absolutely right. The food was incredible. The décor? Just okay. But you don’t come to Osteria da Fortunata for the ambiance—you come for the pasta. And it more than delivers.
The one spot in Florence that comes to mind with a wait that is totally worth it is family run restaurant, Vine y Vecchi Sapori. You may be seated with strangers, but that'is part of the fun. Their menu changes daily. (See the menu we had in photo gallery.)
Another thing I noticed—and loved—was the effortless sense of design in so many Italian restaurants. It wasn’t flashy or overdone, but thoughtful in the smallest details. One of my favorite touches? The way some spots coordinated their placemats with their wallpaper or furniture. I was especially charmed by something I’d never seen before: a single placemat designed to serve two guests at once—running vertical across the table rather than placing one mat in front of each person. It’s subtle, maybe even something you’d miss if you weren’t paying attention—but it adds to the aesthetic and ambiance in a way that makes the entire dining experience feel intentional and artfully composed.
And to my fellow Americans: Dining out in Italy is not rushed. The service is unhurried, and you’re meant to sit, relax, and enjoy. Don’t fight it. That slower pace is part of the magic.
Final Thoughts
This wasn’t the kind of trip you plan six months in advance. It was spontaneous, imperfect, and wonderful.
We wandered early morning, worked during the day, and enjoyed the night, and let the week unfold without pressure. But more than the views or the food, the magic came from the time we created together.
This trip gave us space to be more than coworkers or parents or problem-solvers. We were just us—walking, talking, dreaming, and reconnecting.
Italy was beautiful, yes. But the real gift was time: time to pause, reflect, and make new memories together.
If you’re thinking about a “workation” of your own, Italy is a great choice—even last minute. Just bring your laptop, a sense of adventure, and a love for carbs.
Enjoy my photo dump from the trip below.
