From the canals and waterways of Venice, the dramatic coastal towns of Cinque Terre and the rolling hills of Tuscany –  Italy is one of the most diverse European countries to visit. One of the best ways I’ve found to experience Italy is by road with the country being well connected by roads through a vast majority of diverse cities, towns and villages – even for drivers like me! 😉

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There are so many epic places to include on your road trip and if you’re anything like me you’ll be pushing yourself to see as much as possible. Yaya and I recently undertook our very own 900Km Italian road trip (in a rickshaw) from Milan to the Amalfi Coast in an intense five day trip… testing our ability to spend 120 hours in a box, with wheels, no larger than 4 metres squared 🙂 Now although it was challenging, it was ultimately refreshing and one that got me itching to start our next road trip!

Following on from this trip, I can’t recommend enough seizing the opportunity to see Italy by road and to that end, I’ve put together some of the key places that should be included in your Italian road trip. Some are relatively easy to get to, others a little more tricky but with a little ingenuity, an explorer’s spirit and a few glasses of wine at your pitstop for the night you’ll get the chance to experience Italy in a unique and utterly brilliant way.

Without further ado, here are 23 amazing places you must include on your Italian road trip.

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Cinque Terre:

one of my favourite coastlines in Italy and a must-see on any road trip around Italy, Cinque Terre is an area around 1.5 – 2 hours drive north of Pisa. The region is charecterised by its dramatic, rugged landscape and of course its 5 picturesque terraced towns:  Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore – that just beg to be explored. One of the best tips we’ve learned so far is to take the train between these 5 towns.

The 5 towns are literally 3 – 5 minutes away from each other by train but a much more treacherous 60 minutes apart by car. The reason I say treacherous is because  I ended up scratching the side of the car on the way to Vernazza – Yaya won’t let me live it down. As you can expect, when we visited for the second time, we parked our car in La Spezia and jumped right on that train! 🙂

If you want to explore more on Cinque Terre, don’t forget to read our complete guide to visiting this beautiful region!  

1) Monterosso al Mare, CINQUE TERRE

Monterosso al Mare in Cinque Terre, Italy - The Photo Diary! [5 of 5] (9)

Monterosso al Mare in Cinque Terre, Italy - The Photo Diary! [5 of 5] (7)

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The most western of all the Cinque Terre ‘Lands’ or towns is Monterosso al Mare. Monterosso al Mare is famed for its much larger beach and open spaces than the rest of the towns. What I love most about Cinque Terre is that they feel like a sort of ‘personality test’ – everyone I speak to likes different towns and there always seems to be one favourite that people like most!

Monterosso al Mare might be my least favourite towns in Cinque Terre – but that’s only because my heart has already been stolen by the colourful houses of Vernazza (I’m all about those colourful houses) 🙂

2) VernazzaCINQUE TERRE

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Vernazza in Cinque Terre, Italy - The Photo Diary! [4 of 5] (9)

Vernazza in Cinque Terre, Italy - The Photo Diary! [4 of 5] (2)

Dating back almost 1000 years, Iconic Vernazza still stands to show us a beautiful piece of historic Italian charm – that I fall in love with again and again. The town felt so beautiful on my first visit and only got better on my second – it really stole my heart!  Don’t forget to see the Church of Santa Margherita and Vernazza’s hidden beach just off Piazza Marconi.

3) CornigliaCINQUE TERRE

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Unlike the four other Cinque Terre towns, Corniglia is not perched right on the sea front, but some 100 metres high on the cliff-top. Yaya and I tried to walk this in the blistering heat at midday… it was a bad idea – I just ended up sweaty, hot, dehydrated and no doubt in a bit of a mess 🙂 the second time we visited we used the connecting shuttle bus from the train station, it only takes 5 minutes or so.

A perfect place to enjoy the views across the magnificent region!

4) ManarolaCINQUE TERRE

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Manarola in Cinque Terre, Italy - The Photo Diary! [2 of 5] (7) Manarola in Cinque Terre, Italy - The Photo Diary! [2 of 5] (6)

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Arguably one of the most photographed towns in Cinque Terre, Manarola is a beautiful place to explore and of course grab a bite to eat! I swear that every time I visit Manarola I put on 4kg in weight! The gelato, the calamari, the wine… it’s all just too good!

5) RiomaggioreCINQUE TERRE

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The most southern village of Cinque Terre, Riomaggiore is a beautiful town to sit back and enjoy your afternoon. Grab some local foods (especially fried calamari) from the street vendors and head straight for the rocky harbour front. Yaya and I spent a good few hours dipping our toes into the sea.

This town is a particularly glorious place to watch the sunset from and perhaps even jump into the sea to cool down from the scorching Italian sun.

6.) Trieste

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Situated in the North Eastern edge of Italy, Trieste is a great place to start (or end) your Italian road trip – mainly due to its geographic location. If your looking for some Austrian schnitzel, some Adriatic aperitifs or even  a chilled out Italian cafe, Trieste has it all. Its turbulent past of being a part of Austro-Hungarian Empire and the largest part of the Hasburg Monarchy has ensured the city benefits from a mix of influences and cultures that make me wanna hop in my mini and zoom to this city.

7.) Lake Como

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Yup, you might just spot George Clooney, Tom Cruise or in fact any other A-list visitor here, but there’s so much more to this destination than its famed visitors. The glacial lake Como is a mere 1.5 hour’s drive north of Milan and only 30 minutes or so from the border of Switzerland. For me, the biggest draw to Lake Como is its natural beauty – especially the dramatic mountainous region that always draws me in!

Don’t forget to hop on the ferries that cross the lake, it’s a perfect way to explore the beautiful towns surround it like Menaggio, Bellagio, and Varenna, to mention but a few of my favourites.

8.) Aosta

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Who doesn’t love a bit of snow, eh? Around 100km or so north of Turin, Aosta is nestled within the Italian Alps. With over 2,000 years of history in this town, Aosta is the perfect town to explore sites such as the Bridge of Grand Arvou and the ancient town walls that still stand to this day! Don’t forget to pack your ski’s too! There are some great (but steep) slopes around the region and the ingress at Monte Bianco to enjoy.

9.) San Miniato

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San Miniato has always gave a warm welcome for (friendly) travellers! Hence why we decided to go! 🙂 As the main town was a major thoroughfare for medieval traders between Rome and the rest of Europe, San Miniato became shaped by its constantly changing population and exchange of exotic and sought after goods. Nowadays, the town still welcomes travellers from all over the world with stunning sites to behold like The Duomo, The Tower of Frederick and the well preserved medieval precinct of the town. We spent the whole afternoon here filling up on local olives.. I swear I must have ate several handfuls that afternoon!

10.) Florence

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I love visiting certain cities more than once, with it being one of my favourites for this…Florence may well be an obvious choice to include on a road trip to Italy, but don’t let its popularity stop you from visiting. In fact, it’s never stopped me… I think this was my fourth time visiting, with each time being completely different and unique.

This beautiful Tuscan city is famed for its Ponte Vecchio which stretches across the Arno River and the Firenze Duomo that proudly stands for all to see across the city. Don’t forget to head up Piazzale Michelangelo for some of the best views across the city.

11.) San Marino

 

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Okay, before Yaya tells me off… San Marino is technically not Italy but is instead a tiny micro-state that I just had to include on this road trip. Considered to be the oldest surviving sovereign state in the world, San Marino is a few hours east of Florence and can be enjoyed over a weekend! I lvoe how dramatic the town looks, almost fairytale-esque!

Don’t forget to visit the  Historic Centre and Mount Titano which have both been recently awarded UNESCO World Heritage Status.

12) Orvieto

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Nestled in south west Umbria, Orvieto stands proud situated on the very top of a volcanic tuff. We stopped here by total accident on the way south to Rome, when we noticed it far away. Orvieto is a great place to relax and spend a day, the historic centre is easily walkable, with its charming cafes and restaurants serving some of its highly prized local white wine.

13.) Rome

 

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Ah, Rome – the home of the Roman Empire, Vatican City and ofcourse Sophia Loren. The historic centre of Rome is a must see stop on your Italian road trip. Driving can be tough in this city, so park up and walk or take the train and use public transport whilst you’re there. Just remember to stamp your bus tickets once you get on the bus… I didn’t realise you had to do this and was thus fined €50 for the pleasure. Urgh!

Rome itself has many sites to see even just outside the city itself! I took four days to explore the city – which gave ample time to also include a day in The Vatican.

14.) Vatican City

 

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Enclaved within the city of Rome, Vatican City is officially the smallest recognised state in the whole world. Home to the Pope (who I didn’t get to meet for tea) 🙁 the Vatican is the beautifully preserved state of the Catholic Church. While here, you should definitely attempt to climb St Peter’s Basilica for the most impressive views across Rome and Vatican City – just take a few bottle of water as my mouth was as dry as a desert once reaching the top. If you fancy keeping your feet firmly on the ground though, take a tour of The Sistine Chapel and the gardens of the Vatican.

As with most popular sights, Just remember to buy your tickets early or be prepared for a few hours wait around peak times.

15.) Pompeii

 

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So we literally zoomed to Pompeii on our way from the Amalfi Coast to Naples Airport – it was a flying visit in the morning, but one I had always wanted to do. We woke up around 6am heading straight to Pompeii to get an early start… only to realise it didn’t open until after 9am.  🙁

You can visit the historic site of Pompeii and even see streets, houses and even people of the town that were desecrated by Mount Vesuvius all those years ago . One of the best ways to see Pompeii would be to arrive there first thing in the morning (after 9am 🙂 ) before it gets too busy. You can also consider partnering a tour of Pompeii with a journey up Mount Vesuvius. Just take your walking shoes with you and an appreciation of heights. 🙂

Amalfi Coast

Arguably one of Italy’s most famous coastlines, the Amalfi coast stretches along the Sorrentine Peninsula in Southern Italy. which I couldn’t wait to visit You can include a few days in the Amalfi Coast when visiting the likes of Pompeii (45 minutes away) and even Rome (3 hours away by car) – so it really is an easy part of Italy to visit. Don’t forget to visit Positano and Amalfi itself – they are spectacularly beautiful towns that are well worth exploring.

16.) Amalfi Town On The AMALFI COAST

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While in the historic port town of Amalfi, do visit the Duomo di Amalfi and the Piazza which both provide stunning views of historic Italy – there’s lots of steps, but well worth it for the beautiful picture you’ll capture!

17.) Positano, AMALFI COAST

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Positano was traditionally a fishing village and wine exporter to its relatively close neighbour of Naples. Nowadays Positano has become one of Italy’s most prized towns for visitors to explore (and it’s easy to see why). Spend a few days relaxing here on your road trip while sipping on a limoncello or two.

18.) Palermo

 

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So I might have been unlucky with the weather in Palermo when visiting… I think it only stopped raining for about 1 hour over the course of 3 whole days, but it didnt dampen my spirit to explore this rustic city in Sicily. What I loved most about Palermo is its mix of both Italian and North African heritage – there really is a diverse mix. While in the city, don’t forget to check out the very eery Capuchin Catacombs where hundreds of preserved mummies are housed. It’s a very surreal experience and something I’ve never done before and might not do again – but worth seeing nonetheless.

If your looking for some great views of Sicily, head up to Mount Pelegrino where there are a range of caves and historic buildings to explore.

19.) Mount Etna

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Like Palermo, Mount Etna is situated on the Island of Sicily (which can be easily reached by car ferry from the mainland), more specifically, on the east coast of Sicily. Mt Etna is considered to be one of the most active volcanoes in the world and is almost always in a state of constant activity. We had booked a driving tour up Mount Etna, but due to the rainy and windy weather it got cancelled 🙁  next time I’m taking the sunshine with me to Sicily! 🙂

20.) Pisa

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An obvious choice for any visitor to Italy! Pisa and its famous leaning tower has become a symbolic representation of Italy across the globe. Pisa’s historic town is relatively small and can be explored in as little as 1-2 days. It’s the perfect place to stop en-route between Cinque Terre and Florence. When we last drove this we stopped for food here and explored the Pisa Baptistry, The Leaning Tower and San Sisto. Don’t forget to strike ‘that cheesy pose‘ when you’re there of course! 😉

21.) Venice

 

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in my opinion, Venice is unlike any other city across the world! Its famed canals, labyrinthine streets, Venetian architecture and gondolas make it a great city to explore over a few days. While you can’t drive in Venice, the city is very easily explored by foot. Yes, you will get lost and no doubt have no clue where you’re heading but that’s all part of the fun of exploring this little city in the sea. While here, don’t forget to visit the Grand Canal, Saint Mark’s Basilica, The Rialto Bridge and The Bridge of Sighs.

Accommodation in Venice can be extremely expensive so if your wanting to keep costs lower – consider options like AirBnB or staying a mere 6 minutes away in the town of Mestre. Trains depart from this town every few minutes directly to Venice.

Wanting To Visit Venice? Read How To Easily Explore All the Sights in Venice…

22.) Montepulciano

 

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I’d like to take credit for ‘finding’ this town, but we accidentally stumbled across Montepulciano, the medieval town in the mountains by complete accident. It was a ridiculously beautiful town to stumble upon, providing a welcome opportunity to fill up on some fresh Bresaola and a little wine (for the non-drivers of course).

Don’t forget to wander around The Palazzo Comunale, Santa Maria Assunta Cathedral and the remaining walls of the city that date back beyond the 14th century.

23.) Alberobello

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A picturesue town that looks like it’s from the movies! Alberobello is characterised by its beautiful architecture and quaint charm dating back beyond the age of enlightenment to 16th century Italy. Many of the historic houses have now become home to local crafts and skills that are showcased for visitors to this wonderful town.

Image via 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9… The rest are ours.

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  • What a great list! And breathtaking photos, as always! I’ve never heard of Aosta, but I definitely want to go now 🙂

    • HandLuggageOnly

      So glad you love the road-trip plan, Barbara. I know what you mean about Aosta… It seems so hidden from everywhere – but such a wonderful and beautiful place to experience.

      Lloyd 🙂

  • Italy is one of my favourite countries, I’d love to do a road trip!
    Lots of love,
    Angie
    SilverSpoon London

    • HandLuggageOnly

      Ours too Angie! Can you imagine how fun an Italian ‘foody’ road-trip would be!

      Lloyd & Yaya x

  • What camera do you guys use?? Some of these images look like HDR… but maybe it’s just good glass. 😉

    • HandLuggageOnly

      We use a wide angle Canon DSLR and a Nikon mid range DSLR (some are also with a mirrorless Panasonic camera). We use all three together as they all take slightly different pics 🙂

      • Thanks much!! I also shoot with a canon DSLR and a mirrorless… but I need to do a better job with the mirrorless! 😉

        • HandLuggageOnly

          Mirrorless has been great for night time photography but we’ve found the shutter speed to be a little less responsive than our Canon DSLR. Although we don’t use HDR techniques, we do edit our photos in Lightroom too.

          🙂

  • Do you guys like cinque terre more than the amalfi coast & positano? Are they completely different? Idk I feel like I’ve always wanted to go to the amalfi coast more, but I would love to know your guys opinion.
    xx http://www.nuunablog.com

    • HandLuggageOnly

      We love Cinque Terre, Emma – it’s such a beautiful area and really easy to travel between the towns by train. They are stunning. Having said that, we spent less than 48 hours in the Amalfi Coast… but if we had to choose…. Cinque Terre* 🙂

      *though, this might change in the future 🙂

      Lloyd & Yaya x

  • Love this, doing a two week stint from Venice to Capri and I cannot wait. I love posts like this. I also really like the more in depth posts of each individual city (like Venice!) and would love to see more of those. 😉

    • HandLuggageOnly

      So glad you like the Kayti – wow! Your trip sounds truly awesome… you’re going to have such an amazing time! Are you driving or heading on the train?

      Can’t wait to hear all about the awesome time you had!

      Lloyd & Yaya 🙂

      • We’ll be flying into Venice and from there renting a car (so we can drive through Tuscany and stop at our own pace whenever we find something rather than waiting for a bus or train stop) and then return the car in Rome. From there we will be taking trains and ferries to our other destinations. Already read your posts on Venice and Montalcino!

        • HandLuggageOnly

          This sounds so amazing! We definitely recommend the car – such a great choice! Honestly, you will probably end up stopping ever 20 minutes or so! hahaha 🙂

          The trains are so easy to – just make sure to stamp your ticket when you get on – I got fined on the bus for that (without realising the process). The trains are the same.

          Can’t wait to hear all about your epic adventure!

          x

  • I went to 11 out of the 23, not too bad 🙂

    xoxo, S

    Sara in LDN

    Follow
    on bloglovin & I will follow back!

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  • Beautiful photos! Italy is on my list for this year – especially Cinque Terre. Hopefully I can see the beautiful sights sometime this Spring!

    • HandLuggageOnly

      Kate, you’ll love Cinque Terre. Honestly it’s such a wonderful place to visit 🙂

  • Great picks! I love Cinque Terre and the Amalfi Coast.

    • HandLuggageOnly

      Thanks so much! Yeah it’s one of our favourites too – so hard to not fall in love with a place like Cinque Terre:-)
      Lloyd & Yaya X

  • Zara

    Thanks for this post! I am hoping to do an Italian road trip this Summer and hope to see as many of these places as possible! Italy is stunningly beautiful.

    • HandLuggageOnly

      You’ll love it Zara! Thanks so much for your comment too. If you have any questions about your trip or where to go, just ping us a little message and we’ll help in any way we can.

      Lloyd & Yaya x

      • Zara

        Thanks guys! It’s really great that you take the time to reply to every comment! You’re one of my favourite blogs for that very reason (and the awesome content too of course).

        • HandLuggageOnly

          Awww, thanks Zara! Honestly, your very kind comment means so much to us both! A big thank you!!! 🙂

          Have a lovely weekend!

          Lloyd & Yaya x

  • It’s always a pleasure to read about something new about Italy. I didn’t know about the existence of so awesome places like Alberobello or Orvieto. Thank you so much for the article!

    • HandLuggageOnly

      So glad you liked! Yay! Orvieto is such a stunning town! 🙂

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  • Mr. Sparkle

    Whoah! Great post!
    Planning a 3 week road trip. There are 5 of us.
    Would you recommend getting trains between larger destinations and then hiring cars in the individual spots? Or just driving the whole thing. Because I imagine we wouldn’t want a car in Cinque Terra ect.

    • HandLuggageOnly

      That’s actually a really great thing to do! Trains are really fast and quick between cities and you’re right about Cinque Terre – take the train… it’s so much easier and you’ll save hours of your day!

      A 3 week road trip sounds immense! What a trip! Wow! Let us know if you have any other questions – we just drove a week around Italy and came back yesterday, so happy to help if we can.

      Lloyd & Yaya

      • Mr. Sparkle

        Thanks! I showed the gang your 23 stops and now they are pretty much our 23 stops too haha

        Will probably shoot you some more questions closer to the time 🙂

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  • Manu from wanderlusttogo.com

    My better half and I decided to spend a week on Rab Island, Croatia, and get there by car in some kind of roadtrip through Switzerland, Italy and Croatia… we planned to do 1-day-stopovers in Lugano, Milano, Verona and Venice, and I really can’t wait for the adventure to start. But reading through this post, it makes me wanna do another roadtrip just to visit all those 23 beautiful places. Love the pictures! 🙂

    • HandLuggageOnly

      Wow, what an incredible trip you planned! That’s such an amazing route. Bet you had the most amazing time!

      So glad you like it too Manu – Italy has some incredible places to discover doesn’t it! 🙂

      Lloyd & Yaya

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