La Dolce Vita: A 14-Day Road Trip through Northern Italy
- Shelby Walters
- Feb 25
- 7 min read
There’s a moment when you land in Italy — somewhere between stepping off the plane and hearing your first "Buongiorno!" when you realize you’re no longer in a hurry.
We started off our Italian tour by flying into Rome, and immediately picking up our rental car from Hertz, and that's when we got our first lesson: Italy runs on its own clock.
Second lesson in Italian culture, Automatic cars are expensive. Manuals are cheaper — but you better know how to drive one. The hills are steep, the mountain roads are winding, and the airport rental counter is not where you want to panic-learn stick shift. And then there’s the waiting. You will wait for your car. You will wait for dinner. You will wait for the check. Eventually you stop fighting it.
And that’s when the magic really begins.
Days 1-4 Tuscany: Where the Air Smells Like Wine
Three hours north of Rome, the chaos fades into golden hills. Cypress trees line narrow roads. The light softens. We arrived in Montalcino just before sunset and checked into Hotel Dei Capitani, perched above the valley like something from a postcard. The view from the windows is as good as the pictures.
We had our first dinner at Taverna Del Grappolo Blu, which felt like being welcomed into someone’s home. Brunello flowed. Pasta came slow. No one rushed us out the door.
The next morning, we drove to Montepulciano and enjoyed lunch at Il Teatro Cucina Toscana, which turned into one of those meals where you stop mid-bite just to look at each other in disbelief.
From there, the wineries began — our first, Azienda Agricola La Lastra, then onward toward Siena.
We only had an afternoon in Siena, and it wasn’t enough. The city center alone deserves hours.
The narrow streets feel untouched by time. If I could change one thing about this portion of our trip, it would have been to stay here longer.
That evening, through Tinggly, we were picked up by our driver to head to the stone walls of Monteriggioni Castle — a fully fortified medieval village built in 1213 to defend against Florence. Dante even referenced it in The Divine Comedy. However, local lore tells of a formidable woman who led the community within its walls — not as a queen in the traditional sense, but as a protector and strategist. In times when men were often away at war, women were not simply waiting at home; they managed land, organized defenses, sustained families, and preserved the heartbeat of the village.
There was one woman in particular who was a leader for the village — strong, calculated, and fiercely protective of her people. She rallied other women alongside her during periods of siege.
The message was clear: the survival of Monteriggioni was not solely written by soldiers, but by women
That narrative carried beautifully into our evening sipping wines and enjoying dinner at Agricola Poggio Ai Laghi. Each of their wines are named after these women, each with a different personality, temperament, and strength.
The next day came Tenuta Casanova.
If you go nowhere else in Tuscany, go here. Their wines are sold only to private clients, many celebrities. The grapes are hand-picked. The balsamic alone is worth the drive. It was intimate, intentional, and easily one of the best experiences and meals of the entire trip.
In San Gimignano, we stayed at La Cisterna. The town is beautiful — but it closes early and is filled to the brim with tourists. The tour buses come in, and once they're gone, the town shuts down. Plan ahead or you’ll be wandering cobblestone streets looking for dinner or sitting in your hotel room.
We spent an afternoon at Il Vicario, making pasta from scratch and full glasses of wine. There’s really something grounding about making your own pasta in the Italian countryside but if it wasn't for this experience, we would've skipped San Gimignano entirely.
It was Lucca that stole my heart (Yes, we stopped in Pisa. Yes, we took the cliché photo at the Leaning Tower of Pisa. You have to!). In Lucca, we stayed at L'Iris B&B in Terrazza and wandered aimlessly — biking the old city walls, popping into wine bars, lingering in little shops. Lucca feels lived in. Less performative. More real. It was my favorite of all the villages we visited in Tuscany.
Days 5-6 Cinque Terre: Where the Sea Meets the Sky
Then we reached Cinque Terre — five tiny villages carved into cliffs along the Ligurian Sea.
We based ourselves in Riomaggiore, which also ended up being our favorite of the five villages. We woke each morning to the sound of waves below our balcony and had beautiful views of the sea. Trains connect the five towns easily, though many hiking trails were closed due to landslides — something to check before you decide to walk between the five villages. Walking along the trails is also rather expensive so if you opt for this route, prepare to pay some troll tolls.
Our dinners at Osteria La Torpedine and Da Dulin were two of our best meals of the trip — seafood so fresh and wine that tasted like heaven.
Two days was enough, but I could have stayed forever just enjoying the views from our balcony. It's that beautiful!
Days 7-8 Lake Como: Soft Mornings & Early Evenings
In Varenna, on the shores of Lake Como, life slows even more.
Ferries take you everywhere you want to go across the lake. Mountains surround the still water. Truthfully, I was vastly unprepared for just how big Lake Como is, but here’s the trick: everything closes early. Plan long days and earlier dinners. Even be prepared for things to be closed during the day.
We spent time wandering Bellagio, the largest of the cities around Lake Como, then had unforgettable dinners at Osteria Quattro Pass and Al Prato both local to Varenna. The latter was our favorite dinner of the entire trip — reservations are highly recommended and it's unlikely that they'll accept walk-ins. We showed up right when doors opened and barely snagged a table and saw many folks be turned away shortly after we were seated.
Days 9-11 The Dolomites: Italy’s Wild, Alpine Soul
Driving north into the Dolomites feels like entering another country entirely. German accents. Austrian influence. Wooden chalets.
We stayed near Alpe di Siusi at Parc Hotel Florian, waking to views of Seiser Alm.
We had a long drive up to the Alpines, so decided to call it early and wake up early to take the cable car up to Seiser Alm, the largest high alpine meadow in Europe and a UNESCO World Heritage site. It was breathtaking but we underestimated how much time to spend here — easily a full day if you rent bikes and explore properly but we had an agenda to get done.
Now let’s talk about Sassolungo. Sassolungo isn’t a meadow — it’s a jagged limestone massif that shoots dramatically into the sky at over 10,000 feet. When you stand beneath it, you feel small in a way that’s both humbling and exhilarating and you can even watch the base jumpers taking their plunge down the mountain.
Where Seiser Alm feels open and horizontal, Sassolungo feels vertical and powerful. This isn't for the weak and be prepared for some adventurous terrain.
If you only have one day here’s how I’d choose:
Want something scenic, flexible, and romantic? → Seiser Alm
Want something iconic, dramatic, and adventurous? → Sassolungo
Ideally, do both. They complement each other beautifully but be prepared to cut one or the other short or spend a full day at both.
From here we drove through Cortina d'Ampezzo, host of the 2026 Winter Olympics, and stayed a bit further away in Domegge di Cadore at Rossodisera. The town was a bit sleepy, but this bed and breakfast was just heavenly. Our hostess greeted us each morning in a dirndl and served homemade breakfast, which was delicious. The house itself was a beautiful wooden cottage with beautiful expansive views. It was a really special place.
The next day, we attempted to hike Cadini di Misurina, but cold rain turned the mountain into a wall of fog. Lesson learned: weather in the Dolomites decides your plans. We also didn't prepare ahead of time. This is one of the most popular hikes in the Dolomites and you need to buy tickets ahead of time. The only reason we made it to the top was likely due to the weather.
After freezing our tails off in fog and rain, we stopped at Lago di Braies for quick photos before the rain chased us away again.
Still — even in imperfect weather — the Dolomites were majestic beyond words.
Day 12 San Marino: A Country Inside a Country
From the Dolomites, we made the long drive to San Marino, one of the smallest and oldest republics in the world, entirely surrounded by Italy.
At Hotel Titano, we embraced cooler weather, quiet streets, and the novelty of saying we’d visited a country within a country.
I was a bit skeptical about stopping off here, but it was one hundred percent worth it.
Day 12-14 Rome: Ending Where It All Began
We closed the loop back in Rome, staying in Trastevere which was lively, charming, endlessly walkable.
We wandered through everything you'd expect as a tourist in Rome. We toured the Vatican City, stood inside the Colosseum, walked the Roman Forum, tossed a coin into the Trevi Fountain, admired the dome of the Pantheon, and lingered in Piazza Navona until the sun went down.
Rome is chaos and history and espresso and motorbikes and marble all at once.
And somehow, after 14 days, it felt exactly right to end our trip here.
What Italy Teaches You
Italy teaches you to slow down.
To sit longer at dinner. To drink the good wine. To plan — but not too tightly. To leave space for magic. To connect with others.
Fourteen days. Countless memories. And still, not enough.
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There’s more adventure coming — and trust me, I’ll bring you with me!
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