Bucketlist Italy Road Trip: Best Hiking, Wine, & Culture (with Map)

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An Italy road trip is one of those bucket list items that begs for a few weeks of vacation, and a certain level of “I do what I want!” attitude. I mean, it is a renowned tourist destination for good reason – the old-school architecture, world-famous art, food that will have you asking for thirds, and history that’s weaved its way into all our cultures – all of it is unlike anything else in the world.

Having traveled up and down Italy several times over the past couple of years, through all seasons, and in all the transportation modes, I can tell you that the best way to experience Italy is via road trip, at your own pace, sometime in the summer or fall enjoying the dolce vita without stressing about planning or a checklist of must-do tourist attractions.

This article is aimed at providing guidance on how to plan a 1-week to 4-week road trip through Italy and includes:

• The how-to of transportation & logistics
• Flexible road trip routes depending on the vibe you’re going for and the time you have
• Best local stops along the way that are must-see in Italy
• Lessons learned about the Italian way of doing things

Italy Road Trip: 1 – 4 Week Route Options

These road trip routes focus on central and northern Italy and take into account a few options depending on how much time you have. Below that, I’ve outlined my 4-Week road trip in detail, and have given notes and tips on how to adjust if you need to be flexible, what to do and see, and how much time is really needed in each spot.

Here are the road trip route options based on how many weeks you have, so you can get an idea before jumping into more detail.

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Italy Road Trip 1 Week

Venice – Verona – The Dolomites – Venice

• Distance: 200 miles (320 km)
• Length of Trip: 5 – 7 days
• Highlights:
  • 4 days hiking the Dolomites
  • 2 days in Venice with gondola rides
  • 1 day, a quick visit to Verona, the home of Shakespeare’s Romeo and Juliet

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Italy Road Trip 2 Weeks

Milan – Lake Como – Lake Garda – The Dolomites – Venice – Milan
⭐️ Most Bang for your Buck Road Trip ⭐️

• Distance: 500 miles (800 km)
• Length of Trip: 12 – 14 days
• Highlights:
  • 2 days exploring Milan
  • 3 days on Lake Como
  • 2 Days on Lake Garda
  • 5 days hiking the Dolomites
  • 2 days in Venice with gondola rides

ALSO CONSIDER: Two weeks in Italy can also be spent in authentic South Italy. It is just as beautiful and ideal for early summer or a late fall trip when the tourists have left and the sun has calmed down a bit. This road trip is about discovering Naples and Sicily!

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Italy Road Trip 3 Weeks

Milan – Portofino – Cinque Terre – Pisa – Florence – Venice – The Dolomites – Lake Garda – Lake Como – Milan

• Distance: 900 miles (1,500 km)
• Length of Trip: 18 – 21 days
• Highlights: Italian Riviera, Tuscany, The Dolomites
  • 2 days exploring Milan
  • 4 days in Portofino & Cinque Terre
  • 2 days around Florence and Pisa
  • 2 days in Venice with gondola rides
  • 5 days hiking the Dolomites
  • 2 days on Lake Garda
  • 3 Days on Lake Como

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Full 4-Week Itinerary

If you had one month at your disposal, here are the things to see and do based on my own travels and advice from local Italians, aka my friends. I’ve included favorite spots and little hidden gems to peek into while on the way.

Milan

I started my road trip in Milan because it’s a great airport hub and offers relatively cheap prices for renting a car. I recommend spending a couple of days exploring Miland and settling into the time zone differences if you’re flying from abroad.

Plus, there is no shortage of things to do in Milan – from historical landmarks to world-renowned museums, the city is insane. Here are just a few of my favorites:

• The Duomo: One of the most iconic buildings in Milan, the Duomo is a must-see for anyone visiting the city. The Gothic cathedral is one of the largest churches in the world, and its intricate design is truly a sight to behold. Inside, the Duomo is equally impressive, with vaulted ceilings and stained glass windows that tell stories of faith and Italian history.
  
• The Last Supper: Another must-see for anyone visiting Milan is Leonardo da Vinci’s “The Last Supper.” The painting is housed in the refectory of Santa Maria Delle Grazie, and it is considered one of the greatest works of art ever created.
  
• The Pinacoteca di Brera: For those interested in art, a visit to the Pinacoteca di Brera is a must. The museum houses one of the largest collections of Italian paintings in the world, and it includes works by some of the most famous artists in history, such as Leonardo da Vinci, Raphael, and Caravaggio.

Of course, because you’re in Milan, you have to do some shopping – either window shopping or for real. The city’s upscale boutiques and department stores offer everything from designer labels to high-street fashion. I had to really control myself on this one!

Portofino

I headed south to the coast to start the road trip after Milan. Situated on the Italian Riviera, Portofino is first on the list. It is a picturesque fishing village that has long been a popular destination for tourists. With its brightly-colored houses, winding streets, and scenic harbor, Portofino is super charming and perfect to get you into that Italian spirit.

In addition to taking in the atmosphere of the village, there are a bunch of little trails to walk on and churches to peek into. Spend a couple of days here dining at the village restaurants or picnicking on the beach – this is a seafood lovers’ paradise.

Cinque Terre

Cinque Terre is a breathtakingly beautiful section of the Italian Riviera. Comprised of five medieval fishing villages – Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore – Cinque Terre is a popular tourist destination for good reason, with each village offering its own unique charm!

PRO TIP: You’ll want to park your car outside of the 5 towns for this one and only take a light bag with you to your lodging – trust me on this one!

Here are some of the top things to do and see in Cinque Terre:

• Hiking: The villages of Cinque Terre are connected by a network of hiking trails, which offer stunning views of the coastline. Visitors can hike from one village to the next, or take a more challenging hike up to one of the nearby hills for an even better vantage point.
  
• Swimming: The Mediterranean Sea is just steps away from each of the villages, making Cinque Terre a great place to take a dip. There are plenty of spots to relax on little beaches or enjoy exploring the rocky coastline.
  
• Wine Tasting: Cinque Terre is home to some of Italy’s best vineyards. Tour a local winery or enjoy a glass of wine with lunch or dinner – either way, you’re sure to appreciate the region’s signature wines.

Pisa

And we enter the Tuscany Region of the road trip! We all know you’re here for the iconic photos, so let’s make this a quick but meaningful stop in Pisa, as there is much more to see in Tuscany.

The Leaning Tower of Pisa is one of the most distinctive buildings in the world, and it’s also one of the most popular tourist attractions in Italy – luckily it’s on the way to our next destination! I recommend taking a long lunch stop here as you’re coming from Cinque Terre and heading down the coast to Castiglione Della Pescaia.

That said, if you stay the night, there’s more to Pisa than just its famous tower. The city is also home to a number of other historic landmarks, including the Cathedral of Pisa and the Baptistery, which is quite beautiful. Whether you’re interested in history or simply want to enjoy some of Italy’s most beautiful scenery, Pisa is definitely worth a short visit.

Castiglione Della Pescaia & Orbetello

If you’re looking for beautiful seaside towns to explore in Tuscany, Castiglione Della Pescaia and Orbetello are these hidden gems that no tourist knows about.

Castiglione Della Pescaia is an idyllic little town located on a picturesque stretch of coastline. It’s easy to spend hours strolling along the seafront or relaxing on the beach in both of these towns. That said, there are also plenty of other things to see and do in Castiglione Della Pescaia. Here are just a few of the highlights:

• Visit the Duomo di Massa Marittima: a beautiful cathedral built in the 13th century that has an impressive façade decorated with marble statues.
• Check out the Museo Archeologico e Storico: Housed in a former Franciscan convent, it has an extensive collection of artifacts from the Etruscan and Roman periods.
• Take a boat trip to Isola d’Elba: Located just off the coast of Castiglione Della Pescaia, this island is a great place to escape the hustle and bustle of the town for a while. You can reach the island by taking a boat from the port.

Orbetello is the other beautiful little town in Italy I think you should adventure to, just further down the coast. Think picturesque streets lined with medieval buildings and lazy boat rides out to the Island of Giglio. There are also several museums and art galleries to enjoy, as well as plenty of opportunities for wine and dine adventures.

These couple of days are for the slow rollers, the non-tourist in you. These towns are where Italians go to relax and take it in, and so it’s an opportunity to be among locals!

Saturnia

While most people flock to Italy for its stunning Mediterranean coastline (and let’s be clear, that’s totally ok!), there is another side to this country that is well worth exploring.

In the heart of Tuscany lies the town of Saturnia, known for its natural hot springs. You can find a number of therapeutic pools to soak in, as well as hiking trails that wind through the surrounding hills, and that is why I’m a fan! It’s off the beaten path and offers a little bit of something extra!

Here are just a few of the many highlights:

• The famous thermal waters of Saturnia are naturally heated waters said to have healing properties. You have to go to at least one of the several public baths and spas throughout the city.
• The Roman Ruins of Saturnia are some of the best preserved in all of Italy, dating back over 2,000 years.
• The Cascate del Mulino is one of Saturnia’s most popular attractions, a stunning waterfall fed by natural hot springs, it is a popular spot for swimming.
• The Palazzo Vecchio is a 14th-century palace that now houses a museum dedicated to the history of Saturnia.

Montepulciano

Montepulciano is a small town in the heart of Tuscany that is best known for its Tuscan wine and stunning Renaissance architecture. The town’s cobbled streets and medieval alleyways are lined with quaint shops and atmospheric cafes, making it the perfect place to spend a day exploring.

One of the highlights of any visit to Montepulciano is a tour of one of the town’s many wineries, where you can learn about the production process of the famous Vino Nobile di Montepulciano and sample some of the local goodies.

Siena

Siena is a beautiful medieval city in Tuscany, similar to the pictures above of Montepulciano. The historic center of Siena is also a UNESCO World Heritage Site, so you know they know how to preserve their history!

Known for its old-school architecture, delicious food, art, museums, and all of the little things that make the Tuscan region special, Siena is yet another little gem on this road trip that is special and low-key.

San Giminiano

San Giminiano is a beautiful hill town in the Tuscan region of Italy and is the last of the little towns on this road trip. It is best known for its medieval towers, which rise up above the town’s red tile roofs.

Visiting San Giminiano is easy as can be because it’s all about exploring the narrow streets lined with traditional shops and restaurants and enjoying the countryside. This little stop on the road trip comes highly recommended by quite a few Italians who visit Tuscany every year, so it’s become part of my recommendations as well!

Florence

Last but not least in the Tuscan countryside is the beautiful city of Florence. The original gangster of the Rennaisance. The home of painters and sculptors like Michelangelo and Rafael. It will have a distinct tourist vibe to it compared to some of the past few days on this road trip, but it’s not quite a big city yet.

I love Florence for many reasons.

• The Duomo is the iconic cathedral that towers over the city.
• The Uffizi Gallery is a must, home to some of the world’s most famous paintings, the gallery offers an immersive experience into Florentine art from the Renaissance period.
• Strolls through Boboli Gardens and the narrow streets of Florence.
• Enjoying a meal at one of the many cafes or Michelin-rated restaurants. Ah! La Dolce Vita!

Venice

One of the most beautiful and interesting cities in the world, Venice is a must-see for any traveler. Built on a network of canals, it is home to a myriad of fascinating sights and attractions.

• Take a gondola ride: A ride in a gondola is the quintessential Venice experience. While it can be pricey, there are plenty of ways to enjoy this activity on a budget. Many gondolas offer discount rates for early morning or late night rides, and there are also several companies that offer group discounts.
  
• Visit St. Mark’s Basilica: One of the most iconic landmarks in Venice, St. Mark’s Basilica is a must-see for any traveler. Located in St. Mark’s Square, this ornate cathedral is free to enter, and its impressive interior is well worth a visit.
  
• Walk around Cannaregio: Cannaregio is one of the busiest and most vibrant neighborhoods in Venice. From its lively markets to its colorful street art, there is plenty to see and do in this area. And best of all, it’s relatively cheap to explore compared to other areas of the city.
  
• Take a day trip to Murano: Murano is a small island located just off the coast of Venice. Known for its glassmaking tradition, Murano is home to several factories and studios where visitors can watch glassblowers at work. A day trip here makes for a great addition to any Venice itinerary.

Verona

On your way out of Venice, heading to the Dolomites, there is a little (not so little actually) town called Verona. If this rings a bell, it’s your high school education slapping you over the head.

Verona is renowned for being the setting of Shakespeare’s Romeo & Juliet and has many ties to the author. Highlights include:

• 1st-century AD Arena, a Roman amphitheater
• 13th-century Juliet’s House (Casa di Giulietta), with a balcony overlooking an archway
• Verona Cathedral, housing 14th-century frescoes
• Castelvecchio Museum, in a restored 14th-century castle
• Piazza delle Erbe, a central market square
• Lamberti Tower, with an 84m-high climbable lookout

The Dolomites

The highlight of the second half of this road trip for me was The Dolomites. Overall I recommend spending about 5 – 7 days in the Dolomites. I visited a few times with friends before, and each time, I spent quite a few hours planning the best route so I could maximize time in one location, minimize driving a huge amount in one day, and also see all of the beautiful spots we had on our highlights list.

My highlights list for things to do and see in the Dolomites:

• Adolf Munkel Hike 
• Cadini di Misurina Ridge Hike 
• Tre Cime de Lavaredo Hike
• Seceda Ridgeline Hike 
• Via Ferrata Tridentina (not for first-timers)
• Paraglide in the Dolomites

📍Where to Stay

I recommend a few towns to get lodging in, each close to certain iconic trails and hikes. If it’s your first time heading into the Dolomites, check out some of my favorite hikes above, and decide what town speaks to you.

Lake Garda

A few hours drive away from the Dolomites is Lake Garda, where we rest our weary feet.

We picked Cola Beach to post up and enjoy the sun. This is AFTER the insane breakfast at Hotel Limone which I cannot say enough good things about! Literally, they have a chef preparing a fresh meat and cheese board fresh and custom just for you.

Happy hour drinks and a light dinner were at Scaloni 20 both nights because this is an absolute gem, and they have a killer Espresso Martini which both of us are absolute suckers for!

Lake Como

From Lake Garda, we headed to Lake Como. The drive was a couple of hours, and the most difficult portion of the drive was the one-car-at-a-time-only streets around the lake to get to our lodging.

Bellagio and Varenna are two of the most beautiful towns and are famous for it. I say this, but the reality of it is that all of the small hidden towns around Lake Como are incredibly charming.

PRO TIP: If you only have a couple of days like us, I recommend doing this Villa Balbianello and Lake Como Walking and Boating Full-Day Tour and hit all of the highlights – including explanations of where George Clooney’s mansion is, how many celebrities truly live around Lake Como, and if Leonardo DiCaprio is in town or not.

A few lessons we learned in Lake Como about transportation:

• The lake is very large and it’s worth staying close to the main ports (Bellagio, Varenna, Como).
• It’s very important to plan out your ferry routes and transfer times for the day because the fast ferries only run to certain ports at certain times (and can take 2 hours to get from the town of Como to Bellagio).
• All ferries are crowded, queues are long for tickets, and lines take forever at some ports due to lack of organization. This is very on brand for Italy sometimes – love it or hate it, it’s the way it is!
• It’s worth renting a private boat if you’re wanting to get around quickly and without the stress of planning ferry logistics. Or just use your car!

And that’s it. From here, you’re off to Milan to complete your month-long journey, return your car, and head home much richer in memories than you started!

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Italy Road Trip Map

Milan – Portofino – Cinque Terre – Pisa – Castiglione della Pescaia – Orbetello – Saturnia – Montepulciano – Siena – San Giminiano – Florence – Venice – Verona – The Dolomites – Lake Garda – Lake Como – Milan

Driving Through Italy

Here are answers to the questions I had when I was planning my road trip through Italy about logistics and transportation.

Renting a Car in Italy

You will need the following 3 things to rent a car in Italy:

• A Drivers License
• A Passport
• An International Driver’s Permit

You can get an International Drivers Permit (IDP) from AAA or the State Department (form here). You do not need to have a AAA membership to go through this application process.

The IDP is valid for 1 year and must be carried with your driver’s license when you’re driving. Be sure to bring 2 passport-style photos with you when you apply for the IDP, your US driver’s license, and a method of payment to cover the application fee (cash or credit is fine).

This is what I use to get the cheapest rental
➡️ Discover Cars ⬅️

Should I rent a car or use public transport?

Good question, especially as Italy is super well connected by trains. While trains are a convenient and cheap way to travel, they are constantly delayed (sometimes by hours) in Italy and can be a pain in the butt logistically – this is the reality.

My advice is to rent a car if you’re going to be traveling around for a week or more, exploring lakes and mountains, little small towns and fisherman villages. And especially if you’re doing any one of the road trips I outlined above.

The only time I don’t recommend a car is when you’re just sticking to one big city, like Milan or Rome, as it can be a nightmare to navigate traffic and parking in these megacities.

Can foreigners drive in Italy?

Absolutely they can! Just make sure you have the right documentation and read up on the common mistakes people make when renting a car in Italy. And then go for it!

How easy is it to drive around Italy?

In my opinion, driving in Italy is the toughest of all other European countries. A few observations I’ve made after multiple road trips in Italy:

1. Only Italians see an invisible 3rd lane in the middle of the road, which is mostly used for general meandering in a passive-aggressive way, and/or to scare rule-abiding westerners out of their respective left or right lanes.
   
2. Italians love to honk… to say hello to their besties on the road, to intimidate you from your lane, to express road rage, and sometimes I think just for fun. Basically, honking is a big part of Italian driving culture, so don’t take it personally when people are consistently leaning on their horns. When in Italy, it’s ideal to use all the means of communication with other cars!
   
3. Watch for the cows, sheep, ducks, and occasional humans crossing the road in the middle of high-speed traffic. Life is like it’s a game of Frogger when driving in Italy.

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Tips for Taking an Italian Road Trip

There are quite a few things to consider when planning your Italian road trip. Here is my advice on when, how, and how much.

Is Italy good for a road trip?

YES! Italy is a popular tourist destination for a reason – it has it all! Historic ruins, beautiful scenery, picturesque villages, and hiking-friendly mountains! So whether you’re planning a romantic getaway, a solo adventure, or a family vacation, Italy is the ideal place to hit the open road while keeping on a budget.

The country has good roads, the food is familiar and delicious, the people are friendly and speak English most of the time, and it’s one of the cheaper countries in Europe to vacation in.

And of course, as you can see from the itinerary, there’s no shortage of things to see and do and memories to create.

How do I plan an Italian road trip?

When planning an Italy road trip, it is important to consider the best route to take, what stops to make along the way, and how to budget for your trip. The 1-week to 4-week road trip options outlined in this post will be a good starting point, but just in case, here’s the process to think through.

✅ STEP 1
Decide which route you want to take based on the amount of time you have. There are a number of scenic drives throughout the country, so it is worth doing some research to find the one that best suits your interests.

✅ STEP 2
Once you have chosen your route, you can start to plan for specific stops along the way. Italy is home to countless historic cities and villages, like Milan and Val di Funes. When deciding which stops to make, it is important to consider how much time you have available and what type of experience you want to have (ie. the activities you are interested in and how long you want to spend in a car/in transport).

✅ STEP 3
Finally, it is important to budget for your Italy road trip. Accommodation costs can vary widely depending on the region and time of year you are traveling. By doing some research in advance and booking accordingly, you can ensure that your Italy road trip is both pleasant and affordable.

What is the best month to travel to Italy?

This road trip is best done in late summer or early fall, anything during the months of July, August, or September. The weather is warm, the lakes are cool and refreshing, all the mountain huts and restaurants are open in the Dolomites, and the sun is out all the time!

Note that August is the most touristed month in Italy because all the kids are off on vacation. This means August will also be the most expensive month as it is peak travel season for Europeans.

How much does a road trip around Italy cost?

It really depends on your activities and travel style but it does not have to break the bank, especially since a lot of things are outdoor activities like hiking & lake sports.

During the peak summer season, these were the average costs for me:

Car Rental: €60-100 per day
Lodging: €80-120 per night
Food & Drink: €60 a day per person
(and here’s some advice on how not to be an a*hole tourist when tipping)

What is the best way to see Italy?

There’s no wrong way to see Italy, but some ways are definitely better than others. A road trip is the best way to see all that the country has to offer, from the vibrant cities to the picturesque countryside.

You’ll have the freedom to explore at your own pace and take detours whenever you please. Plus, you’ll get a taste of the real Italy away from the tourist traps. Rent a car and hit the open road – it’s the best way to see Italy!

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Final Thoughts: Why A Road Trip in Italy Is A Must!

Italy is a country with something for everyone – stunning coastlines, rolling hills, dramatic mountains, picturesque villages, and cities brimming with culture and history. Here are just a few reasons why a road trip to Italy should be on your bucket list.

• Italy has some of the most scenic drives in the world. From the Amalfi Coast to the Tuscan countryside, there are endless opportunities to explore beautiful landscapes.

• Italian culture is friendly, easygoing, and welcoming. Traveling in Italy is like being welcomed into an old friend’s house just as they are preparing for a meal, and they’re so glad you’re joining them!

• An Italy road trip gives you the flexibility to travel at your own pace and create your own itinerary. While it’s easy to get caught up in the hustle and bustle of city life, a road trip allows you to slow down and really appreciate the present.