Two Week Northern Italy Road Trip Itinerary

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.

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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

Northern Italy Road Trip: Day 1 and 2 – Milan to Lake Como

Arriving in Milan is easy from any airport; follow the signs to pick up your car, check your Tripit app for your address to your accommodation in Lake Como, and begin your road trip to Northern Italy. 

Travel time from Milan to Lake Como

Depending on the airport you are flying into, allow 2 hours (to be on the safe side). Parking in Como can be difficult, so check with your accommodation before arriving. Dish to try – Antipasto originated in the Alps and is a great meal to enjoy while you people-watch in one of the alfresco restaurants.

Accommodation in Como

Splurge – Vista Palazzo 

This small luxury hotel is in a prime location overlooking one of Italy’s most famous lakes. Everything about it feels luxurious, parking is available, and breakfast is included. When you only have a short time to spend in one of my favourite places in Italy, this location ticks all the boxes.

Budget – Hotel Plinius

The Hotel Plinius is clean and basic, has friendly staff, and is in a great location. The room has an ensuite and a Juliette balcony overlooking the streets of Como. The beds are a little more complicated than I would like, but this place is ideal for the cost. It does have parking, which is a bonus in this part of Italy.

Things to do in Lake Como

If you only have one day to explore, you can walk around Como, visit the cable car, have dinner at one of the fantastic waterfront restaurants, or drive to neighbouring towns. The ferry pier is within walking distance and a beautiful way to visit Menaggio. If you choose to spend more than one day here (which I highly recommend), then read ten reasons why I fell in love with Lake Como for more things to do in and around Lake Como.

Tour recommendation: Lake Como and Bellagio tour

Northern Italy Road Trip: Day 3 Lake Como to Milan

With Lake Como only a short distance away, set off early and head to Milan to explore the well-known sites. Milan is known to be one of the world’s fashion capitals, and if you are there long enough, you can see why. Dish to try – Ossobuco, a speciality in this part of the country. 

Accommodation in Milan

Splurge – The Street Milano

Located at Via Santa Radegonda 14, Milan City Centre, 20121, walking distance to Duomo. The staff are friendly, and the rooms are modern, with an edgy feel topped off with the perfect rooftop breakfast area. There are parking facilities available and accessible wifi.

Budget – Amabilia Suites

The location could not be any better. Perfect place with a direct view of the Duomo. The downfall to Amabilia Suites is there is no parking on-site, and children under 18 are not permitted. 

Things to do in Milan

Spend the entire day exploring Milan with major tourist spots like La Scala Opera House, World Heritage site Santa Maria Elle Grazie (where the painting of the Last Supper by Leonardo Da Vinci hangs), Duomo di Milano and Castello Sforzesco. 

Tour recommendation: 3-hour walking tour

Northern Italy Road Trip: Day 4 and 5 Milano to Verona

After breakfast, head out to Verona (the city of love), where the feel of Romeo and Juliette is dotted all over this beautiful city. This city is small but so beautiful. It does get very crowded during peak season, so ensure you book your tours and accommodation early. Dish to try – Baci di Giulietta; in English, it is Juliette’s kiss. Okay, so this isn’t a dish, but head to any bakery in Verona, where you will find these delicious treats.

Travel time from Milano to Verona

Depending on your route, allow 2-2 and a half hours. When you arrive in Verona, the streets are narrow, so parking is complex, and many areas are metred parking. 

Accommodation in Verona

Splurge – Due Torri Hotel 

Due Torri Hotel is at Piazza Sant’Anastasia 4, Verona Historical Centre, 37121 Verona. This excellent hotel has a great location and friendly staff close to Sant’Anastasia and Romeo’s house. Private parking is possible at a place nearby, but a reservation is needed and will incur a daily cost. 

Budget – The Best Western Armando

Best Western Hotel Armando is located in the heart of the historic centre of Verona, within walking distance to the Roman Arena, Piazza Delle Erbe and most of the tourist spots. The rooms are clean, and the staff are friendly, but no parking is available. 

Things to do in Verona

Spend the day exploring this romantic city and relax by Verona di Arena with an aperitif in the afternoon. Better still, go during Opera season and enjoy a night at the Arena listening to the Opera. If you want a more detailed itinerary about what to do in Verona in 1 day, check out the post here.

Recommended tour: 3-hour bike tour

Northern Italy Road Trip: Day 6 Verona to Trento

After breakfast, head out to Trento. Trento is a beautiful city situated in the district of Trentino(just south of the Dolomite Mountains). Trento is very close to Lake Garda, where you can spend an extra day travelling and have more time. Dish to try – Gnocchi Cadorini is the best example of this region, bringing Germanic and Italian traditions to life. 

Travel time from Verona to Trento

Allow 1 to 1.5 hours, and enjoy the gorgeous countryside. Stop to take photos if you need to; this part of Italy’s travel is spectacular and should be appreciated more for its journey than just its destination. 

Accommodation in Trento

Splurge – Hotel Norge

Hotel Norge is found at Trada Del Norge 3, 38123 Norge, about 5km from Trento city centre. The views here are hard to beat at any other place during this trip. The location might not be in the city centre, but these views are stunning. It has a spa centre and heated pool, something hard to find on this trip.

Budget – Al Cavour 34 

Al Cavour 34 is a pensione (bed and breakfast) with the most friendly staff, delightful rooms and cutest little balconies. Located in a central position in this gorgeous town. Wake up each morning to the sound of the cathedral bells and the smell of freshly baked cakes. Unfortunately, there is no parking at the pensione, but the staff will help you sort it out.

Things to do in Trento

This small town has many incredible tourist spots, from the Castello del Buonconsiglio to the Duomo di Trento. The city itself might be small, but it has a huge heart and lots of history to go with it. Whether you spend the entire day in the town or take a day trip to Lake Garda, there are many choices. If you want a more in-depth itinerary, “The Best of Trento in 1 Day.” would be a great place to start.

Recommended tour: Dolomites full-day excursion

Northern Italy Road Trip: Day 7 Trento to Venice

This northern part of Italy is a must! Everyone knows Venice and wants to tick off the city of canals on their bucket list! Venice is everything you can imagine. There is so much to do here, so one day on this Road trip wasn’t enough. Drink to try- Aperol Spritz, although it was thought to have been developed during the Austro-Hungarian Empire when the soldiers found Italian wine too strong to drink, added a spritz to their wine!

Travel time from Trento to Venice

Give yourself 2-3 hours, depending on whether you take the scenic route via Lake Garda. If you do, stop by, take some photos and spend some time in this area; it is beautiful. You can not park your car in Venice, so park at Tronchetto Parking Station first and then hop on public transport to your accommodation. To make things easier, you can purchase your ticket online. 

Accommodation in Venice

Splurge – St Regis, Venice

Anywhere in this city is a splurge! However, you will find that accommodation is more expensive here than in most areas of your trip. St Regis is a beautiful hotel located at San Marco 2159, San Marco, 30124, in a great location, Venetian style decore and a fabulous view. The downfall is this hotel is for adults over 18 only! 

Budget – Pensione Accademia – Villa Maravege

Anywhere in Venice, it is an excellent location because there is something special around every corner. Pensiones are your best choice in Venice, and Pensione Accademia – Villa Maravege is in a great area within walking distance of the Gallerie Dell’Accademia.

Things to do in Venice

There are many beautiful places to visit in Venice, but the must-visits are the Basilica San Marco, The Rialto Bridge, Doge’s Palace, and Gallerie dell’Accademia. There is pretty much something spectacular around every corner, including a gondola ride through the canals.

If you want something unique, try booking tickets to Opera here, at one of the many venues in this fantastic floating city. If you have more time up your sleeve and choose to stay here a little longer, I would highly recommend an island tour as a day trip.

Recommended tour: Venice walking tour

Northern Italy Road Trip: Day 10 Venice to Pisa

After breakfast, return to your car and head to the beautiful city of Pisa, where the Leaning town of Pisa is more striking in real life than ever captured on film or in a book. You can not help but be mesmerized by its beauty as soon as it pops its head into view! Finally, Cecina is a dish to try; not to be confused with the nearby town, it is a chickpea flour pancake; trust me when I say it is delicious!

Travel time from Venice to Pisa

This part of the road trip to Italy will take about four hours, so be prepared! You have a few options of places to stop off on the way. Firstly, you could stop off in Ferrara (where the city centre is included in UNESCO’s World Cultural Heritage list).

You could also stop at Bologna, where the famous dish Spaghetti Bolognese (or at least very close by) originated! Or, of course, the more well-known city of Florence where you will find the statue of David and, of course, try a gelato where this world-famous creation was born.

Accommodation in Pisa

Splurge – Borgo Suite

Borgo Suite is close to everything. The apartment has plenty of room and can accommodate three couples easily. The staff are friendly, and the Borgo Suite is highly regarded, so book as soon as possible! It is just under one km from the Leaning Tower of Pisa. Street parking is available in this area.

Budget – Hotel Villa Kinzica

For a budget accommodation hotel, Villa Kinzica is ideal for staying if you want the shortest walk to the Leaning Tower of Pisa. This mid-18th-century villa should not be overlooked! Public parking is nearby, but apart from that, this is a great little hotel, rooms are clean, and the staff are friendly.

Things to do in Pisa

Book your ticket to the Leaning Tower of Pisa early, as this is where you will find the most extensive line, then continue on the day by exploring the square of miracles, which includes Museo dell Opera del Duomo, Cathedral Of Santa Maria Assunta, The Baptistery of San Giovanni, Camposanto, and Museo delle Sinopie. Other places to visit are The Palazzo dei Cavalieri and the River Arno. 

Recommended tour: Three hours guided tours of Pisa

Northern Italy Road Trip: Day 12 Pisa to Sienna

Leaving Pisa after breakfast and heading to Siena’s beautiful medieval world heritage site. It is one of Italy’s most visited cities! So whether you are lucky enough to stay on the 16th of August when the Palio race (it’s still number 1 on my bucket list) or, like many others, you are there to discover why everyone loves this gorgeous city, you will not be disappointed. Dish to try – Pici alle briciole, a simple Tuscan pasta dish to ensure your mouth tingles when you finish. 

Travel time from Pisa to Siena

This part of your Northern Italy itinerary will take approximately 2 hours. There is some beautiful Tuscan scenery to enjoy along the way. When they say the sweeping hills of Tuscany, you will know exactly where that phrase comes from as you drive through an actual real-life painting. 

Accommodation in Siena

Splurge – Grand Hotel Continental Siena – Starhotels Collezione

The name of the hotel says it all. The Grand Hotel Continental Siena is an architectural delight. It is in a great location, and it’s worth staying just for the view of the city. This 17th-century building is within walking distance of the Piazza Campo, and although there is no parking at the hotel, there is parking at a nearby parking station for a fee. 

Budget – La Terrazza Sul Campo

The view from this place is incredible! The rooms are clean, the staff are friendly, and the proximity to Piazza Campo is hard to beat. The downfall is that there is no parking, but if you are willing to walk a little, you can find parking in other areas of the town. 

Things to do in Siena

Your north Italy road trip is almost ending, and what a place to end! This gorgeous little medieval town is jam-packed with touristy things to do and see. However, if you are here for the day, you must start at Piazza Del Campo, where you can visit Piazza del Duomo, climb to the top of Torre Del Mangia and take your photo at the Fonte Gaia.

Other places of interest include the Santa Maria Della Scala Museum and Pinacoteca Nazionale (The National Gallery of Siena). If you decide to stay longer, try a dinner in the Tuscan countryside or a wine tour around this fabulous world-class wine region.

Recommended tour: Siena City tour

Northern Italy Road Trip: Day13 Siena to Milan

It is almost the end of your ultimate northern Italy road trip, and our final day is spent heading back to where it all began: Milan! There are a few places you can stop along the way, including Bologna, Parma, famous for Parmigiano Reggiano cheese and Prosciutto di Parma, both Italian staples. Otherwise, you could take a detour along the coast and spend some time in Genoa (the birthplace of Christopher Columbus). 

Travel time from Siena to Milan

This will be your most extended day trip yet, especially if you choose the scenic coastal trip. It will take you a minimum of 4 hours without stopping! However, if you choose the more scenic coastal route, expect to add another hour to your drive. 

Northern Italy Road Trip: Day 14 Explore Milan

Whether your last day in Milan is spent indulging in Milan’s local cuisine or riding the on-off bus to the places you have yet to explore, it is up to you! So relax and enjoy your last day in this beautiful country!

💡 My Top Tips for This Northern Italy Road Trip

1. 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.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.

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