7 Days in Italy: When Travel Doesn’t Go as Planned (But You Still Make It Work)
Our week in Italy didn’t go exactly as planned — there were hospital visits, slow days, and plenty of gelato-fueled recovery time. But between Florence’s golden skyline, Bologna’s comforting pasta, and Venice’s quiet canals, we still found the magic of travel — even when it wasn’t perfect.
A one-week Italy itinerary through Florence, Bologna, and Venice — with a dose of real-life travel chaos and how we made the best of it.
Italy had been on our travel wish list for years—art, history, pasta, and wine all wrapped up in a week of adventure. What we didn’t expect was that our trip would turn into a crash course in rolling with the punches. Between my sudden GI illness and my husband’s lingering cold, we learned firsthand that sometimes travel isn’t picture-perfect. Still, even when things don’t go as planned, Italy has a way of shining through.
Traveling childfree gave us the flexibility to adjust quickly—no nap schedules, no extra logistics—just the two of us figuring out how to make the best of things. Here’s how our 7 days in Italy itinerary unfolded, health hiccups and all.
If you enjoy honest, low-fuss itineraries, check out my 5-day North Island New Zealand Itinerary.
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Day 1: Florence Arrival
We landed in Florence in the afternoon and dove straight into Italian life with dinner at All’Antico Vinaio, famous for its enormous sandwiches stuffed with local ingredients. Fueled up, we strolled the city: gazing at the Duomo at golden hour, crossing the Ponte Vecchio, and soaking in sweeping views from Piazzale Michelangelo. It felt like the dream start to the trip we’d been planning.
Highlights
Duomo (Cathedral of Santa Maria del Fiore): Florence’s most iconic sight, this grand cathedral dominates the skyline with its red-tiled dome and marble-striped facade. Climb to the top for sweeping city views or simply admire its architectural brilliance from the square below.
Ponte Vecchio: A medieval bridge with a storybook feel, Ponte Vecchio is lined with jewelry shops that shimmer in the sunlight. Stroll across for postcard-perfect views of the Arno River — especially as the evening lights start to glow.
Piazzale Michelangelo: Perched above the city, this famous viewpoint offers one of the most breathtaking panoramas in Italy. Come at sunset to watch Florence bathe in golden light as the Duomo and Arno River stretch out below.
Duomo (Cathedral of Santa Maria del Fiore)
Day 2: An Unplanned Hospital Adventure
In the middle of the night, things took a turn—I became violently ill and ended up taking an ambulance to the hospital. After hours of IV fluids, bloodwork, and waiting, I was discharged around 4 a.m. With no taxi showing up, we walked back to our hotel in the dark, exhausted but relieved.
While I spent the day recovering (thank goodness for HGTV in Italian), my husband explored Florence solo. It wasn’t what we envisioned, but it was a reminder that sometimes travel forces you to slow down—whether you like it or not.
Day 3: Catching Up in Florence
Still weak but determined not to waste the day, I rallied. We headed to Mercato Centrale for a casual lunch, climbed Giotto’s Bell Tower for views over the city, and wandered Piazza della Signoria, Florence’s open-air gallery of statues and history. We had to cancel our Tuscany wine tour, but making it out at all felt like a victory.
Highlights
Mercato Centrale: A paradise for food lovers, Mercato Centrale brings together local vendors serving fresh pasta, pizza, cheese, and wine under one roof. It’s the perfect place to sample regional flavors and refuel between sightseeing.
Giotto’s Bell Tower: A masterpiece of Gothic architecture, Giotto’s Bell Tower stands tall beside the Duomo, wrapped in colorful marble panels. Climb its 414 steps for one of the best views of Florence — including the Duomo itself.
Piazza della Signoria: Florence’s open-air museum, this lively square is filled with sculptures, fountains, and Renaissance grandeur. Snap a photo with a replica of Michelangelo’s David and soak in centuries of history all around you.
Piazza della Signoria
Day 4: Bologna Detour & Onward to Venice
By now, my husband was starting to feel the tickle of a cold just as I was barely recovering. Still, we made it onto the train for Bologna, where we joined a food tour at Mercato delle Erbe. Tagliatelle al ragù, tortellini in brodo, and other regional specialties gave us a much-needed morale boost. Then it was onward to Venice, where the winding canals would become both our playground and our sickbed.
Highlights
Mercato delle Erbe: This indoor market is a local favorite for fresh produce, cured meats, and casual eateries. It’s an authentic taste of Bologna’s food culture — best enjoyed with a glass of wine during your food tour.
Fresh pasta in Bologna
Day 5: Venice in Shifts
I was improving, but my husband’s cold was in full force. We took things slowly: walking over the Rialto Bridge, sitting in Piazza San Marco, and enjoying lunch before visiting Teatro La Fenice, Venice’s storied opera house. We moved at half-speed, but Venice rewards wandering, even when you’re dragging your feet.
Highlights
Rialto Bridge: The oldest and most famous bridge in Venice, the Rialto is a must-see spot for classic canal views. Visit early in the morning or at dusk to beat the crowds and watch gondolas glide beneath.
Piazza San Marco: Venice’s grand central square, surrounded by elegant arcades, St. Mark’s Basilica, and the Campanile tower. It’s busy but beautiful — best experienced with a coffee in hand and time to linger.
Teatro La Fenice: One of Italy’s most historic opera houses, La Fenice is a stunning example of Venetian elegance. Even if you don’t see a performance, the guided tour offers a glimpse into its lavish golden interior.
Piazza San Marco
Day 6: Survival Mode
At this point, neither of us was at 100%, so we took our time as we wandered the city. We toured the Bridge of Sighs and Basilica di San Marco early, then retreated for coffee and pastries in Cannaregio (the Jewish Ghetto). The afternoon included quirky chocolate tastings at Nino and Friends, browsing at Libreria Acqua Alta, and squeezing down Calle Varisco, Venice’s narrowest street. It was a mix of sightseeing and resting in equal measure.
Highlights
Bridge of Sighs: An ornate limestone bridge connecting the Doge’s Palace to the old prison, the Bridge of Sighs is steeped in legend. Its name comes from the sighs of prisoners glimpsing Venice for the last time through its small windows.
Basilica di San Marco: This glittering Byzantine masterpiece is a feast for the eyes, filled with golden mosaics and intricate details. Arrive early to avoid crowds and take in the sheer opulence of Venice’s most famous church.
Cannaregio (Jewish Ghetto): Venice’s most authentic and peaceful neighborhood, Cannaregio offers quiet canals, cozy cafés, and deep history. It’s the perfect escape from the city’s bustle — ideal for a slow morning coffee or evening stroll.
Libreria Acqua Alta: This quirky bookstore is famous for its overflowing stacks of books stored in bathtubs and gondolas to protect them from floods. Don’t miss the book staircase in the courtyard — it’s one of Venice’s most Instagrammed corners.
Calle Varisco: Known as one of Venice’s narrowest streets, Calle Varisco is a fun, blink-and-you’ll-miss-it stop. Wander through for a quick photo and the novelty of squeezing down a passage just 53 cm wide.
Bridge of Sighs
Day 7: Murano & A Classic Gondola Ride
For our final day, we leaned into lighter joys: a ferry ride to Murano to watch glassblowers at work, gelato in the sun, a gondola ride through Venice’s side canals, and a quiet visit to Chiesa di San Zaccaria. It wasn’t the energetic finale we’d imagined, but it was quietly memorable.
Highlights
Murano: Just a short ferry ride from Venice, Murano is world-famous for its centuries-old glassmaking tradition. Watch artisans at work or browse the island’s boutiques for one-of-a-kind souvenirs.
Gelato: Because no trip to Italy is complete without it. From creamy pistachio to stracciatella, it was joy in a cone.
Gondola Ride: Touristy, yes—but drifting through side canals is still Venice at its most magical.
Chiesa di San Zaccaria: A hidden gem near St. Mark’s, this quiet church holds Renaissance masterpieces and an atmospheric crypt that often floods with lagoon water. It’s a peaceful break from Venice’s main sights.
Gelato makes everything better!
Travel Tips for When You’re Sick (Because It Happens!)
No matter how much you plan or prep, sometimes your body has other ideas. Getting sick on vacation is the worst — especially when you’re in an unfamiliar country. But here’s what we learned from our experience.
1. Don’t push yourself.
It’s tempting to power through, but rest really does speed up recovery. Missing one tour is better than being down for three days because you overdid it. Let yourself nap, stay hydrated, and embrace the slower pace.
2. Know where the nearest hospital or clinic is.
You hope you’ll never need it, but if you do, you’ll be grateful to know where to go. Bonus: no astronomical U.S. hospital bill (if you’re outside the U.S.).
3. Always have travel insurance.
It’s not glamorous, but it’s the adulting side of childfree travel. A good plan covers medical emergencies, canceled tours, and extra hotel nights if needed. It’s peace of mind you won’t regret. We use Blue Cross Blue Shield Global Solutions (full disclosure: we have not filed a claim with them).
4. Keep a mini “sick kit” in your bag.
Pack electrolyte packets, anti-nausea meds, Imodium, ibuprofen, and cold medicine at minimum. You can find pharmacies in many countries, but having your own stash saves you when an illness hits and buys you time to figure out where to get medicine if you need it.
5. Adjust expectations — not your attitude.
Some of our favorite travel memories come from the unexpected. Watching HGTV in Italian while eating crackers wasn’t on the itinerary, but it became part of the story. Travel isn’t always picture-perfect, and that’s okay.
6. Take turns caring for each other (if you’re traveling with a partner).
When you’re traveling as a couple, teamwork matters. One person might be exploring solo (and picking up meds from the local pharmacy) one day while the other recovers. It’s part of navigating life while traveling.
Final Thoughts: When Travel Gets Messy
To be totally honest, this wasn’t the trip we pictured. We missed Tuscany’s rolling hills, had to cancel plans, and spent more time nursing ourselves back to health than sipping wine. But here’s what we learned:
Travel rarely goes perfectly. Even in Italy.
Traveling childfree gave us the flexibility to adapt. We didn’t have to juggle kids’ needs on top of our own, which made it easier to slow down when we needed to.
Sometimes the best memories come from the unexpected. Like watching Italian home-renovation shows in a hotel bed, or laughing at the absurdity of walking home from the hospital at 4 a.m.
Italy reminded us that travel isn’t about checking boxes—it’s about the experience, however messy it might be. And sometimes, the stories you didn’t plan for are the ones that stick with you the longest.
Have you ever had a trip go sideways? How did you make the best of it? Share your story in the comments!