Anyone who’s had Italy on their bucket list has almost certainly pictured Northern Italy specifically — the lakes, the vineyards, the cities that all somehow look like paintings. If you’re anything like me and staying in one place was never going to cut it, a road trip is genuinely the best way to see it properly.
Table of Contents
This itinerary covers a well-tested 14-day route through eight stops — Milan, Lake Como, Verona, Trento, Venice, Pisa, and Siena — with enough time in each place to actually enjoy it rather than just tick it off. It’s built for travellers who want the big landmarks without missing the smaller, quieter moments in between — the drive through the Dolomite foothills, an aperitivo in a piazza, a bakery you’d never have found otherwise.
✈️ Quick Resources
- 📱 Stay connected: Airalo — new users get 15% off. I came to eSIMs late and wish I hadn’t — it’s saved me hundreds of dollars since.
- 🚗 Car hire: DiscoverCars — Especially worth it for a two-week trip.
- 🛡️ Travel insurance: SafetyWing — affordable, reliable, and easy to set up. Choose your dates and coverage; that’s it.
- 🛂 Visa: iVisa — check whether you need a Schengen visa and sort it in a few clicks before you fly.
- 🎟️ Tours & experiences: GetYourGuide — browse experiences and use code trulyexpattravel10 for 10% off via the app.
🌤️ Best Time to Visit Northern Italy
Spring (March–May)
Mild weather and thinner crowds make spring one of the best windows for this route — the countryside between Verona and Trento is especially beautiful once things start turning green.
Summer (June–August)
Hot and the busiest by far. Venice, Verona, and Siena all get genuinely crowded, and driving between cities is more pleasant early in the day before the heat sets in.
Autumn (September–October)
My pick for this trip — warm enough for evenings in a piazza, cooler for the driving days, and noticeably quieter at the big sights.
Winter (November–February)
Quiet and often beautifully atmospheric, particularly in Venice, though some smaller-town attractions run reduced hours and Lake Garda day trips are less rewarding in the cold.
Peak vs Off-Season
July and August, plus the weeks around Verona’s Opera season, push both prices and crowds up considerably. If your dates are flexible, shoulder season (April–May or September–October) gets you the best balance.
Crowd Levels
Verona and Siena in particular get very crowded during peak season — book tours and accommodation early if you’re travelling in summer.
✈️ How to Get to Northern Italy
Flying In
Milan is the natural starting point, and it’s genuinely simple to arrive from any airport — you’ll just need to know which one your car hire is booked at.
Car Hire
Your road trip isn’t complete without organising this first. Hiring a car from any of the Milan airports is simple — I highly recommend DiscoverCars, where you can book online, compare deals, and have the car ready when you land.
💡 Tip: Milan has three international airports — Malpensa, Bergamo, and Linate — so make sure you book your car at the correct one.
Important note: many cities, including Bologna, restrict parking within the historic city walls to protect the old towns. Research parking for each stop before you arrive — most tourism sites list the correct information.
Getting Around & Planning Your Route
Book all your accommodation online before you arrive, then link your bookings, tours, and transport into the TripIt app — it’s a genuine game-changer for mapping out an itinerary this long before you set off.
🗺️ The Route: 14 Days Through Northern Italy
Here’s the route in full before we get into the detail of each stop:
- Day 1: Milan to Lake Como
- Day 2: Explore Lake Como
- Day 3: Explore Milan
- Day 4: Milan to Verona
- Day 5: Explore Verona
- Day 6: Verona to Trento
- Day 7: Trento to Venice
- Day 8: Explore Venice
- Day 9: Explore Venice
- Day 10: Venice to Pisa
- Day 11: Explore Pisa
- Day 12: Pisa to Siena
- Day 13: Siena to Milan
- Day 14: Explore Milan
🚙 Day 1–2: Milan to Lake Como
Arriving in Milan is easy from any airport — follow the signs to pick up your car, check TripIt for your Lake Como address, and you’re off.
Travel time: around 2 hours depending on which airport you fly into. Parking in Como itself can be tricky, so check with your accommodation ahead of arrival.
💡 Tip: Antipasto originated in the Alps, and this region does it beautifully — a great one to order while you people-watch at an alfresco waterfront restaurant.
Where to Stay in Como
- Splurge: Vista Palazzo — a small luxury hotel in a prime lakeside location — everything feels indulgent, parking is available, and breakfast is included.
- Budget: Hotel Plinius — clean, friendly, and well located, with an ensuite, a Juliette balcony over the streets of Como, and — a genuine bonus in this part of Italy — parking.
Things to Do in Lake Como
With one day, you can walk around Como itself, ride the cable car, have dinner at one of the waterfront restaurants, or drive to a neighbouring town. The ferry pier is within walking distance and a lovely way to reach Menaggio.
If you can stretch to more than one day here — which I’d genuinely recommend — my 10 reasons why I fell in love with Lake Como post covers more of what’s worth doing in and around the lake.
Tour recommendation: Lake Como and Bellagio tour
🚙 Day 3: Lake Como to Milan
Lake Como is only a short distance from Milan, so set off early and spend the day exploring the well-known sights. Milan has earned its reputation as one of the world’s fashion capitals, and a full day here makes it obvious why.
💡 Tip: Ossobuco is a Milanese speciality — worth ordering at least once while you’re in the city.
Where to Stay in Milan
- Splurge: The Street Milano — walking distance to the Duomo, with friendly staff, modern rooms, parking, and a rooftop breakfast area that’s worth the stay alone.
- Budget: Amabilia Suites — an unbeatable direct view of the Duomo — just note there’s no on-site parking and it’s adults-only (18+).
Things to Do in Milan
Spend the day taking in La Scala Opera House, the World Heritage site Santa Maria delle Grazie (home to Leonardo da Vinci’s Last Supper), Duomo di Milano, and Castello Sforzesco.
Tour recommendation: 3-hour walking tour
🚙 Day 4–5: Milan to Verona
After breakfast, head to Verona — the city of love, with Romeo and Juliet’s story woven through it at every turn. It’s small but genuinely beautiful, and it gets crowded in peak season, so book tours and accommodation ahead.
Travel time: 2–2.5 hours. Streets in Verona are narrow, so parking is tricky and much of it is metered.
💡 Tip: Baci di Giulietta — ‘Juliet’s kisses’ — aren’t a dish so much as a treat, but any bakery in Verona will have them. Worth seeking out.
Where to Stay in Verona
- Splurge: Due Torri Hotel — a great location near Sant’Anastasia and Romeo’s house, with friendly staff. Private parking is available nearby but needs a reservation and a daily fee.
- Budget: Best Western Armando — right in the historic centre, walking distance to the Roman Arena and Piazza Delle Erbe. Clean, friendly, but no parking on-site.
Things to Do in Verona
Spend the day exploring, and relax by the Arena with an aperitivo in the afternoon. Better still, time your visit for Opera season and catch an evening performance at the Arena di Verona. A small-group walking tour with Arena tickets included is a good way to combine both.
For a more detailed one-day itinerary, see the best of Verona in 1 day.
Tour recommendation: 3-hour e-bike tour
🚙 Day 6: Verona to Trento
After breakfast, head to Trento — a beautiful city in the Trentino district, just south of the Dolomites, and close enough to Lake Garda that it’s worth an extra day here if you have one to spare.
Travel time: 1–1.5 hours through genuinely spectacular countryside — this is a leg to appreciate for the drive itself, not just the destination.
💡 Tip: Gnocchi Cadorini is the dish to try here — a good example of the Germanic and Italian traditions that blend in this region.
Where to Stay in Trento
- Splurge: Hotel Norge — about 5km from the city centre, but the views here are hard to beat anywhere else on this trip — plus a spa and heated pool.
- Budget: Al Cavour 34 — a central pensione with friendly staff, delightful rooms, and cathedral bells to wake up to. No on-site parking, but staff will help you sort it.
Things to Do in Trento
This small town has a genuinely big heart — from Castello del Buonconsiglio to the Duomo di Trento, there’s plenty of history packed into a compact centre. Whether you spend the whole day in town or take a day trip to Lake Garda, you’ve got options. For a more in-depth plan, see the best of Trento in 1 day.
Tour recommendation: Dolomites full-day excursion
🚙 Day 7–9: Trento to Venice
This part of Northern Italy is unmissable — everyone dreams of ticking Venice, the city of canals, off their list, and there’s genuinely so much to do here that one day on this route wouldn’t have been enough.
Travel time: 2–3 hours, depending on whether you take the scenic route via Lake Garda — worth the detour if you have time to stop for photos. You can’t park in Venice itself, so leave your car at Tronchetto Parking Station and hop on public transport to your accommodation — buying your ticket online ahead of time makes this far smoother.
💡 Tip: Aperol Spritz is thought to have originated during the Austro-Hungarian Empire, when soldiers found Italian wine too strong and cut it with a spritz. Order one at any canal-side bar.
Where to Stay in Venice
- Splurge: St Regis, Venice — beautiful Venetian-style décor, a fabulous view, and — as with most of Venice — a splurge-level price tag. Note it’s adults-only (18+).
- Budget: Pensione Accademia – Villa Maravege — a lovely area within walking distance of the Gallerie dell’Accademia — pensiones like this are usually your best value option in Venice.
Things to Do in Venice
The must-visits are St Mark’s Square and Doge’s Palace, the Rialto Bridge, and the Gallerie dell’Accademia — with something spectacular around pretty much every corner, gondola ride included.
If you want something a little different, opera tickets at one of the city’s many venues are worth booking. With more time up your sleeve, an island tour to Murano and Burano makes a great day trip.
Tour recommendation: Venice walking tour
🚙 Day 10–11: Venice to Pisa
After breakfast, collect your car and head to Pisa — the Leaning Tower is even more striking in person than in any photo, and it’s genuinely mesmerising the moment it comes into view.
Travel time: around four hours. There are a few worthwhile stops along the way — Ferrara, whose city centre is UNESCO-listed; Bologna, birthplace of the dish that inspired Spaghetti Bolognese; or Florence, home to the statue of David and, fittingly, the birthplace of gelato.
💡 Tip: Cecina — a chickpea flour pancake, not to be confused with the nearby town of the same name — is genuinely worth trying in Pisa.
Accommodation in Pisa
- Splurge: Borgo Suite — plenty of room, easily fits three couples, under a kilometre from the Leaning Tower, and highly regarded — book early.
- Budget: Hotel Villa Kinzica — a mid-18th-century villa with the shortest walk to the Leaning Tower — clean, friendly, with public parking nearby.
Things to Do in Pisa
Book your ticket to the Leaning Tower of Pisa early, as the queue here is the longest you’ll face all trip. Afterwards, explore the Square of Miracles — the Museo dell’Opera del Duomo, Cathedral of Santa Maria Assunta, the Baptistery of San Giovanni, Camposanto, and Museo delle Sinopie — plus the Palazzo dei Cavalieri and the River Arno.
Tour recommendation: 3-hour guided tour of Pisa
🚙 Day 12: Pisa to Siena
Leave after breakfast for Siena’s medieval old town — a UNESCO World Heritage site and one of Italy’s most-visited cities. Time it for 16 August if you can catch the Palio race, still top of my own bucket list, or simply arrive to see why everyone falls for this place.
Travel time: around 2 hours, through some genuinely beautiful Tuscan countryside — the ‘sweeping hills’ cliché makes complete sense once you’re driving through it.
💡 Tip: Pici alle briciole — a simple Tuscan pasta dish — is worth ordering here.
Accommodation in Siena
- Splurge: Grand Hotel Continental Siena – Starhotels Collezione — a 17th-century building within walking distance of Piazza del Campo — worth staying for the view alone. Parking is available nearby for a fee.
- Budget: La Terrazza Sul Campo — an incredible view and unbeatable proximity to Piazza del Campo, though you’ll need to walk a little further for parking.
Things to Do in Siena
Start at Piazza del Campo, visit the Piazza del Duomo, climb Torre del Mangia, and take your photo at Fonte Gaia. The Santa Maria della Scala Museum and Pinacoteca Nazionale (Siena’s National Gallery) are also worth a look.
If you’re staying longer, try dinner in the Tuscan countryside or a wine tour around this world-class wine region.
Tour recommendation: Siena city tour
🚙 Day 13–14: Siena to Milan
The final leg brings you back to where it all began. Along the way, consider stopping in Bologna, or in Parma — home of Parmigiano Reggiano and Prosciutto di Parma, two proper Italian staples — or take a coastal detour to Genoa, birthplace of Christopher Columbus.
Travel time: your longest day-trip leg — a minimum of 4 hours without stopping, plus another hour if you take the scenic coastal route.
Spend your final day in Milan however suits — more of the local cuisine, or hopping on the Milan hop-on hop-off bus for anything you missed first time round.
🍴 What to Eat on This Northern Italy Road Trip
- Antipasto (Como) — this shared starter plate has its roots in the Alps, and it’s the perfect thing to order while people-watching at an alfresco waterfront restaurant.
- Ossobuco (Milan) — a Milanese speciality of braised veal shank, rich and slow-cooked, and worth planning a dinner around.
- Baci di Giulietta (Verona) — ‘Juliet’s kisses’, a bakery treat found all over the city rather than a restaurant dish, and a sweet way to remember Verona.
- Gnocchi Cadorini (Trento) — a good example of the Germanic-Italian crossover in this region’s food, worth trying while you’re in Trentino.
- Aperol Spritz (Venice) — thought to date back to the Austro-Hungarian Empire, when soldiers cut strong Italian wine with a spritz. Order one canal-side.
- Cecina (Pisa) — a savoury chickpea flour pancake, distinct from the town of the same name, and genuinely worth seeking out.
- Pici alle briciole (Siena) — a simple, rustic Tuscan pasta dish, hand-rolled and served with breadcrumbs — comfort food at its best.
- Parmigiano Reggiano & Prosciutto di Parma (Parma, en route) — if your route takes you through Parma, both are worth tasting at the source.
💡 My Top Tips for This Northern Italy Road Trip
- Book accommodation, tours, and especially Verona’s opera season tickets well ahead — this route hits several cities where peak-season crowds and prices climb fast.
- Link everything into TripIt as you book it. With eight stops and this many moving pieces, having one app that maps your whole itinerary out is worth the ten minutes it takes to set up.
- Research parking before you arrive in each city — historic centres like Bologna restrict access altogether, and even where it’s allowed, metered and complex parking is the norm rather than the exception.
- Remember Venice is car-free — leave your car at Tronchetto Parking Station and book your public transport ticket online in advance to avoid queuing on arrival.
- Build in slow days where you can. The drives themselves — especially Verona to Trento, and the Tuscan hills into Siena — are as memorable as the destinations.
- Pack layers if you’re travelling shoulder season — this route moves through lake, mountain, and coastal climates, and temperatures shift more than you’d expect over two weeks.
❓ Frequently Asked Questions
Final Thoughts on This Northern Italy Road Trip
What I love most about this route is how different each stop feels from the last — a lakeside town, a fashion capital, a city built on a love story, a mountain town, a floating city, a leaning tower, and a medieval hilltop centre, all within two weeks and one hire car. Go slowly where you can, say yes to the detours, and let the drives between cities be part of the trip rather than just the means to an end.
✈️ Plan Your Trip
→ Book tours and tickets with GetYourGuide — code trulyexpattravel10 for 10% off
→ Get connected with an Airalo eSIM before you land
→ Book your hire car with DiscoverCars before you fly
→ Sort your cover with SafetyWing — essential for a trip this length
📲 Follow Along
Follow along on Instagram where I share real-time travel updates, behind-the-scenes moments from tours, and daily life in Singapore. Join the Truly Expat Facebook community — a supportive space for women travellers to ask questions, share tips, and connect before trips.
- Instagram: @trulyexpattravel
- Facebook: Truly Expat
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