A Last-Minute Italy Trip With Five Friends (and Zero Sleep)
Spring break 2024 started the way all great trips do: with a half-baked plan, five friends from college, and a borderline irresponsible budget. We found an Airbnb in Luminasio for about $1000 bucks split five ways, grabbed a rental car for around $650, and booked flights back in November for roughly $620 each. The only real goal was simple—cram as much of Italy as humanly possible into one week. Sleep would have to figure itself out later.
The Travel Chaos Starts Before Italy Even Begins
The universe decided to spice things up before we even left the country. Our first flight out of Phoenix got delayed, which meant our connection waiting for us in San Francisco would leave without us before we had a chance to land. One of the airline employees was determined to help us with this and managed to get us on a flight to Los Angeles, with a new connecting flight to Rome leaving the next morning. We headed off to LAX without any boarding pass or evidence of our promised connecting flight besides the word of this airline worker. After arriving at LAX and asking around we were told which terminal to show up to the next morning. Thankfully, the airline covered a hotel and dinner, turning our first night of the trip into a weird, unexpected vacation limbo.
Standby Seats to Rome and Reuniting With the Crew
The next morning involved hustling between terminals, waiting on hold for airline support, riding the standby list like a roller coaster, and somehow landing seats to Rome. One friend had flown separately and was already there waiting for us since the night before. The very first thing we realized when we met up? I was the only one who had actually remembered to bring an international driver’s license. That instantly made me the official driver for the rest of the week—whether I wanted that responsibility or not.
My opinion: Driving in the cities is somewhat stressful but driving on the highways and countryside is easy. Choosing to rent a car was our best decision of the trip.
Washing Off Jet Lag in the Tyrrhenian Sea
We picked up the rental car, threw our backpacks in the trunk, and started the drive north toward Medelana. At some point along the coast, we spotted a dirt road pull-off with signs indicating a beach. We pulled off and swapped into some swim shorts before pushing through some brush to find a black sand beach pouring into the Tyrrhenian Sea. Two of us decided that this was the perfect place to wash the plane off us, and stripped shoes, socks, shirts, and ran straight into the water.
Still soaked, we walked back toward the car, but not before following a cat which looked at us crazy for swimming.
We were obviously out of swimming season. After brushing the sand off and getting back on the road, we pulled into a grocery store for snacks and drinks, then finished drive following long and winding road into the hills toward our Airbnb—an old stone cabin tucked into the green countryside.
Note: If you are renting a car in Italy, chances are it will be manual and quite small if you’re on a budget. None of this was an issue for us, but the road to our house required first and second gear when we drove it with all our luggage and people. We hardly used any gas for the trip however!
Our First Italian Feast in a Tiny Village Restaurant
That night we walked to the only nearby restaurant, which was conveniently down the hill, a cozy local spot without a single tourist in sight. Our server was incredibly friendly, and instead of ordering, we told him to choose for us. He responded to us something along the lines of, “Alright, do you want all of the kinds of prosciutto?”. He eventually brought us four or five platters of different meats and cheeses, red and white wine, and several dishes of different pastas. Everything he brought out was incredible, rich, and fresh. After a long and social dinner, he tried to convince us of some dessert, but we stood our ground being filled to the brim already.
Exploring Florence: Duomo, David, and Wandering Until 1AM
The next morning, we hit Florence. As everywhere we visited, you could spend a week there, but we had our planned spring break mayhem. We visited the Duomo, walked inside Santa Maria del Fiore, and gazed at the statues peeking out from every corner and window.
We spent the rest of the night wandering narrow alleys, eating gelato, people-watching, and soaking in the history shear time spent creating beauty all around us. By the time we got back to the car, it was nearly 1am, but we hadn’t noticed. It was well worth the time spent.
Pagani and Lamborghini: A Dream Day for Car Enthusiasts
The next day was dedicated to the car lovers in the group. We started at the Pagani Museum in Modena, a small, immaculate building where every car looks like art and even the bathroom feels like it belongs to a design magazine. The cars are the most beautiful I have ever seen but obviously they aren’t just for show as we noticed small chunks of tire rubber melted to some side skirts. It does seem strange to gawk over a bathroom, but when you see one with tasteful carbon fiber everything and leather handles you will also bring all your friends in with you just to see. From there, we drove through open countryside to the Lamborghini Museum, soaking in V12 engines, prototypes, and the insane history behind some of the world’s wildest cars. Personally, the Pagani Museum far superseded the Lamborghini, but maybe I like Pagani’s more. Can you really blame me?
Venice at Sundown: Pastries, Canals, and Late-Night Wandering
After a quick lunch, we headed east to Venice. Some of the group enjoyed a car nap in the backseat. By the time we parked, the sun was dipping behind the canals, giving everything that soft orange movie glow.
We wandered across bridges, through quiet alleys, past bakeries selling pastries that smelled like heaven. During the wandering, my friends got to try her new old film camera she had gotten just before the trip. We devoured some sweets and savories, took photos by the canals, and eventually found a late-night dinner spot. Venice looked surreal—almost plucked out of a movie. Unfortunately, looks aren’t everything, and the canals had quite a stench to be smelled. By the time we made it back to the car, it was long past midnight, but somehow, we still had enough energy to chat for the first hour or so of our drive home.
Accidentally Driving Into Bologna’s Restricted ZTL Zone
The next day we caught up on some sleep and stayed closer to home and drove into Bologna, a beautiful city. Here, we encountered our first and only driving scare. I had dropped some of us off to use the restroom while I searched for parking, and accidentally ended up driving into one of Bologna’s restricted ZTL zones. This road seemed like it was a crosswalk going under buildings, but luckily we made our way out quickly.
That night we tried to make homemade pizza in our Airbnb. It ended up becoming more of a calzone due to our questionable technique, but it tasted amazing after three days of chaos. We closed the night watching Inglourious Basterds, a weirdly perfect choice.
A Perfect Countryside Morning and the Best Beignets of My Life
The next morning we took the long, scenic backroads toward Milan and stopped at a tiny countryside café that looked like nothing special from the outside. Inside? Life-changing pastries. The beignets were the best I have had in my life.
The Alfa Romeo Museum and a Night Stroll Through Milan
In Milan, we toured the Alfa Romeo Museum which was by far the most detailed and expansive of the museums we’d seen. The exhibits on aerospace engineering were especially cool since some of us work in that industry.
When the sun went down, we walked to Sforzesco Castle in time for the walls entrance gates to be shut in front of us, but glow of the castle walls were beautiful enough for me. Milan at night is one of those places where the streets feel alive, even when they’re quiet.
Getting Lost in Bologna’s Architecture and a Local Flea Market
The next day we decided to explore Bologna properly. Its architecture is stunning—endless covered psorticos, warm colors, a rhythm to the streets that feels older than time. We stumbled onto a local flea market selling everything from Soviet-era watches to antique cameras to war memorabilia and vintage clothes.
We bought a few things, took group photos, and had our final late dinner at the restaurant in the hills again before returning home.
The 2AM Drive Back to Rome and the End of the Adventure
Our alarms went off at 1:30am. I had some espresso and by 2am we were on the road, winding through dark highways back toward Rome. Everyone else slept while I drove—the unofficial chauffeur until the very end.
We dropped the car, dragged ourselves into the airport, and boarded our flights home. The trip was a blur, but the good kind—the kind that stays with you.
What I Learned From a Week of Driving Across Italy
You can plan a trip, or you can just go and let the country guide you. We chose the latter, and it gave us late-night dinners in Venice, unexpected swims in the Tyrrhenian Sea, and quiet castle nights in Milan.
If you want to see Italy in a week, rent a car, bring friends who don’t mind chaos, and say yes to everything. Sleep is optional. Memories are not.
