Italy is one of the iconic countries of the Mediterranean: with its rich history and breathtaking landscapes, it is a must-see when visiting Europe. After many years dreaming of dolce vita, I finally made it happen. I designed a two-week road trip of Italy through its most idyllic destinations, from Genova to Palermo! I made sure to cover the classics as well as more surprising destinations off the beaten path. If you know me, you know I love authenticity and connection. I am not afraid of a little adventure and love to learn about culture and history!
Our objective was to explore new places every day, while allowing for plenty of rest, especially towards the end of our road trip. We wanted to stop by big cities, such as Florence and Rome, visit famous coastal towns including Portofino and Positano, but also discover lesser known villages in Cinque Terre, the Amalfi Coast, and beyond. Those ended up being our favourites. Finally, we wanted to end our road trip with one week in Sicily, where we mostly relaxed and enjoyed water sports.
We decided to rent a car because we wanted to move around freely over the two weeks. It is, however, perfectly possible and comfortable to move around via public transport, at least for the first half of this itinerary. Once you reach the South of Italy, infrastructure is less developed, including transport. For more tips on how to rent a car for a cheap price in Italy, click here.
In the itinerary below, I only mention the visits, restaurants, and hotels which we genuinely enjoyed and thought were worth sharing. This way, you get only quality recommendations. None of them are based on partnership and we paid for everything ourselves. If this sounds like a guide you’d follow, keep reading for a full guide to discovering Italy!
…wanna get started in the right mood? Check out my playlist below!
Day 1: Genova
We started our two-week Italian road trip in the capital of the Liguria region, with plenty of time to wander in the picturesque streets of Genova. This port city, once the home of Cristopher Columbus, is filled with narrow passages, exuberant churches, and opportunities for apericena – drinks accompanied by small dishes such as bruschetta, cold cuts, and cheese. We loved its simplicity and surprising beauty.
Some suggestions on what to do: visit the St Andrew cloister ruins and the reconstruction of the childhood home of Christopher Columbus, get lost in the streets of the historic centre, or listen to street musicians at Piazza Raffaele de Ferrari. Wondering where to eat? Get cocktails and apericena at Il Cavaturaccioli and dinner in the area of Piazza Fossatello, where there are various authentic restaurants.
Day 2: Portofino & Cinque Terre
Portofino
We wanted to have breakfast in Portofino before heading to Cinque Terre. We were deeply disappointed with the restaurants directly on the port, which were all incredibly expensive and did not look tasty at all. Instead, I recommend packing a small bag of pastries from the area or finding a more isolated local bakery where you can find a focaccia or panino for less than 5€.
Aside from this, we loved the colours and charm of Portofino, which definitely has a very luxurious atmosphere. It was still pretty quiet when we arrived, before 10 AM. We left Portofino by 11 AM and, when leaving, we noticed that the police was controlling the massive influx of cars into town. I therefore recommend arriving early, to avoid crowds but also to avoid getting stuck at the entrance of Portofino!
Monterosso Al Mare
We had lunch in Monterosso al Mare, one of our favourite locations of the whole trip! We could enter the resident-only area with our car by telling the local traffic agent that we had a restaurant reservation (kudos to Agustín, who thankfully speaks Italian which helped us tremendously throughout the trip). With luck, we parked close to the Buranco Winery in the heights of Monterosso, and hiked all the way down which I recommend because this is where we got the best views of the area. Absolutely breathtaking!
We had lunch at L’Ancora della Tortuga, an excellent restaurant which featured several times in the Michelin guide in the past. It only had a few tables available, the food was among the best we’ve had, and the beach views from there were fantastic. Afterwards we headed to the beach, where you can rent a sunbed or lay your towel on the beach, depending on the area.
Vernazza
Finally, we arrived in Vernazza arounf 6PM and it was a lovely time to see the the warm sunlight hit the mountains and colourful buildings. We had a drink at Ristorante Bar Al Castello, which has wonderful views. Afterwards, we grabbed some street food which we ate on the port. There was a very joyful and bucolic atmosphere. The perfect way to end the day!
Note: If you have the time, I recommend checking the other villages that constitute Cinque Terre: Manarola, Riomaggore, and Corniglia. They all have their individual charm and are easily accessible by train.
Day 3: Tuscany — Lucca and Florence
Lucca
On our third day driving through Italy, we explore two jewels of Tuscany: Lucca and Florence. Lucca is a charming town which thrived as a trading hub and enjoyed patronage from the influential Medici family during the Renaissance. It is famous for its well-preserved city walls, which now serve as a scenic promenade.
In Lucca, we first stopped at the Piazza dell’Anfiteatro, a circular square built on the site of a Roman amphitheater now filled with cafes and shops. Then we visited the Guinigi Tower, once owned by a ruling family of Lucca. It stands out from the other few remaining towers because of the trees which were planted on its top – a truly unique view!
Florence
In Florence, we were staying in a beautiful family home turned into a bed and breakfast, which was perfectly located just outside of the city center in an area that featured lots of greenery and parking. We loved the atmosphere and service, which made us feel like Italian aristocracy! In the city, of course you can’t miss the Palazzo Vecchio, the Cathedral of Santa Maria del Fiore, and the Ponte Vecchio.
If you are looking for a nice gift or are a fan of stationary (as me), you must stop by one of the Signum shops. I won’t say more, just prepare to be marvelled. Finally, We had an absolutely fantastic dinner at Trattoria Napoleone, with the best pasta dish of my life so far (gnocchi with gorgonzola and truffle). The restaurant terrace is set on a quiet square which was the perfect escape from the busy city centre.
Day 4: Rome
Ah… Rome! In only 24 hours?! Yes we did it, and we had the most epic time thanks to friends and locals, who helped us make the most of our stay and feel like true Romans. Here is everything we did in the Eternal City:
🎧 listen to Everything Everywhere Daily podcasts about Rome to learn its mesmerising history
📸 see the beautiful Piazza Navona
🍝 eat freshly made pasta at Osteria Da fortunata (@osteria_da_fortunata_official) (there are several locations in the city… all will most likely have a waiting line!)
🏛️ admire Roman architectural feat at the Pantheon
⛲️ make a wish at the magnificent Fountain of Trevi
🏺 travel back through history at the archeological sites of the Roman Forum
🏟️ marvel at all sides of the Colosseum
🛴 rent a @tier.mobility e-scooter and drive around the city
👒 get a custom-made straw hat at @giuncart
🛍️ shop local designs and vintage clothing along Via di Monserrato, Via del Pellegrino, and Corso Vittorio Emanuele II, including @chezdede and @humanavintageitalia
🍸 drink aperitivo at @jacopa.it with a soft sunset over Rome’s hills from Trastevere
🍴 eat the best (and most) Italian food of our lives at @daenzoal29 – again, prepare to queue, but so worth it!!
We had a splendid sleep at Domus Giulia, a simple but very well located hotel in the old city centre. It was just perfect!
Day 5 & 6: Amalfi Coast, Positano, and surroundings
We decided to skip Napoli and the ruins of Pompei on our way to the Amalfi Coast because we knew it was going to be very hot and just preferred to go straight to the coast at this stage of the road trip. However, those cities are definitely on my list so I hope I can return soon and would recommend anyone to stop by, especially if they are interested in Ancient Rome, Pompei being one the world’s best preserved archeological sites.
Breathtaking Hotel Views
We strategically booked hotels that were outside of the most famous and touristic towns of the Amalfi Coast such as Positano, Praiano, Amalfi, and Salento. It was a great decision. We wanted to avoid the crowds and the expensive prices without compromising on views.
First, we stayed at an old farmhouse in the mountain of Vico Equense: Il Casale del Golfo. It had breathtaking views of the Gulf of Napoli and the mountains – it was quite rural but we loved the atmosphere and being welcomed like family (the owner, who had connected with Agustín, almost cried when we left). If the rustic comfort throws you off, I still can highly recommend their restaurant. It attracts locals and tourists from all sides in the evening, with a spectacular sunset view.
The next day, we stayed at Grand Hotel Sant’Orsola in Agerola, which literally felt like a dream. It had the most epic view from our balcony and breakfast terrace, which I will never forget. The hotel was truly off the radar, not on major booking platforms and seemed to prioritise weddings and receptions. The room needed a bit of new paint and refreshing but the service staff was truly out of a movie, such characters! We felt like in an Italian version of “The Grand Budapest Hotel”.
In sum, we highly recommend booking accommodation off the beaten path in popular areas such as the Amalfi Coast. This allows avoiding crowds, attractive prices, and more authentic experiences.
Boat Trip on the Amalfi Coast
By far, the best part about the Amalfi Coast was renting a boat for the day and admiring the wonderful views of Positano, Positano, Arienzo, Laurito, Praiano, Conca dei Marini, Amalfi (and more) from the water. Agustin has a contact in Sorrento who rented us a boat which does not require a license and is relatively easy to drive for connoisseurs (here). We had packed some sandwiches, a bottle of wine, some snacks, and towels to be comfortable.
This day was pure happiness and will definitely go down as one of the best days of my life. Being in on the water and able to jump and see small creeks, cascades, and rock formations from up close (we even saw dolphins!!!!!!!!!!!!!!!) was magical. It also allows to see the beauty of these villages perched on the cliff of the shore without the craziness of the traffic and crowds of the land. The next day, when driving around the villages, we barely wanted to stop because of how hectic it was.
Vietri sul Mare
Out of all the villages we visited on the Amalfi Coast, I liked Vietri sul Mare the most. It is known for its ceramics and colourful walls made of mosaiques. It was very cute and not so crowded as other stops. We bought beautiful ceramics with the emblematic lemons of the region at Ceramiche Sara.
Day 7: Scalea
Scalea and the neighbouring towns in the region of Calabria were are best surprise of the road trip. First, we stayed at a fantastic vintage hotel, Grand Hotel de Rose, which once again made us feel like we were on the set of a movie. The decoration, groovy atmosphere, and amenities were impeccable, for a price ridiculously low. The domain is scattered with vintage furniture and antiques, making it particularly picturesque. There were few foreigners in Scalea and it was so much more tranquil than the Amalfi Coast, with yet absolutely amazing sea and mountain views.
Nearby, you can visit the famous Spiaggia dell’Arcomagno in San Nicola Arcella which is only 10 min away. Opening hours are 8am-8pm but it closes when reaching maximum capacity (avoid arriving at peak hours). Just 5 min further, I highly recommend Il Clubbino for sunset: one of the most beautiful ones I’ve seen in my life! The panoramic view over the small port, surrounding forest, and dreamy mountains in the background made it truly exceptional.
Crossing to Sicily island
The next day we made our way to Sicily which was quite a long drive. To cross onto the island and biggest region of Italy, we took a ferry which you don’t necessarily need to book in advance and costs about €35. It takes about 20 minutes to do the crossing from Villa San Giovanni to Messina and boats depart every 20 minutes. We used the company Caronte Tourist and you can directly book on their website here (avoid comparative platforms which always end up selling for more than the ticket price). I literally almost had a breakdown after being scammed but it’s honestly much easier than it seems.
Side note: the further south you get in Italy, the more likely you are to be scammed, in my experience. Especially in Sicily, we checked every single one of our receipts and multiple times the staff from restaurants and shops were adding stuff we had not ordered. Beware! The beauty of Sicily’s history, architecture and nature thankfully makes it up.
Day 8-10: South of Sicily, Valley of Temples, Stair of the Turks
During our first days in Sicily, we stayed in a beautiful family owned vacation house: Madre Landmade. It is in the countryside of Ragusa, a small town in the south of Sicily. There wasn’t much around, but we decided to go there for the quietness and relaxation. It was absolutely perfect. Everything was home-made (soap, jams, cakes,…) and home-grown or locally sourced (tomatoes, cheese, eggs, hams,…), the views were magnificent, especially in the morning when the light was warm and soft, and the surrounding sounds of nature were truthfully therapeutic.
After so many days on the road, we were exhausted. We did not leave the house aside from a quick grocery trip, which in itself was an entire highlight because of the freshness and deliciousness of the produce we could find for a fraction of the price you would pay in other parts of Europe. I cooked pasta dishes and lemon chicken with the help of our generous hosts who provided fresh basil from the garden. This was for the quintessential holiday for me, and this place reminded me of my childhood vacation in the south of France.
Valley of the Temples
On our way out of Ragusa we stopped at the Valley of Temples in Agrigento, an awe-inspiring archaeological site that took us on a journey through ancient history. It is a vast domain with remarkably well-preserved temples dating back to the 5th century BC. Walking through this open-air museum, we felt transported to a time when these temples stood as symbols of power and grandeur.
The most prominent among them is the Temple of Concordia, dedicated to the Greek goddess of harmony. As you explore the site, you’ll also encounter the Temple of Hera (Juno), Temple of Zeus, and Temple of Heracles, each bearing its unique architectural features and stories of the past. Surrounded by rolling hills and olive trees, you’ll have breathtaking views of the Sicilian countryside.
🎟️ tickets cost us 10€ per person – they have discounts for students of philosophy/architecture/history and youth below 26
🔥 avoid visiting between noon and 3pm (unlike us) or get ready to feel a scorching sun
🕙 open until 11pm in high season, which means you can visit during sunset and make the most of the panoramic views
Stair of the Turks
Then, we stopped by the Stairs of the Turks, a coastal formation consisting of white cliffs that resemble steps leading down to the turquoise-blue waters of the sea. It had some of the most heavenly-looking beaches I’ve ever seen! We still had a bit of road and it was quite a hike to go down and up to and from the beach, so we decided to admire it from above. However, if you have time, I’d highly recommend going down to swim in the tropical-looking shallow waters. Fun fact: the name “Stairs of the Turks” is said to have originated from the frequent raids carried out by pirates along the coast centuries ago, thought to be Turkish.
Day 10-14: North of Sicily, Erice, Palermo, and Taormina
During our last days road tripping through Italy, we stayed in the North-West part of Sicily. It was a quiet and beautiful area, with plenty of charming villages to discover and nature to explore. We stayed at La Tonnara di Bonagia, which is a resort hotel installed in a former tuna fishery. The buildings reminded me of a medieval castle, it was a unique scenery. The clientele mixed families and couple, which resulted in a little too many kids running around to be really relaxing, but the service and amenities were great. We had direct access to the beach through a private area that led to the crystal-clear waters of a scenic bay with mountain views in the background. Idyllic.
We wanted to visit San Vito Lo Capo, the nearby islands of Favignana, as well as Cefalu (please do if you get the chance), but ended up taking it more slowly and visiting other spots nearby. Agustín also followed some kite-surfing lessons in an area close to Marsala, which was a very popular spot because of its shallow waters and strong winds.
Erice
We visited the small village of Erice, perched on top of a mount of the same name. Its history dates back to ancient times, with evidence of human settlement in the area as early as the Bronze Age. The town has seen the rise and fall of various civilizations, leaving behind a rich cultural heritage and making it a UNESCO World Heritage site today. Several walking paths are offered to visitors throughout town to discover its history. The highlights, in my opinion, were the Tower of King Federico, the little hidden streets, and the fantastic views from the castle of Balio.
Overall, Erice made me feel like I was in a fairytale: the beautiful castles, 360 views, cobblestone streets, and old houses all created a particularly dreamy atmosphere. I bought beautiful ceramics in local shops on Via Roma, where prices were considerably cheaper than most other places in Sicily. In addition, given how secluded this village was, I wanted to contribute to the economy of the local artisans and shop holders who keep the beauty of Erice alive. We had dinner at Ristorante Monte San Giuliano, which had a magnificent view and delicious pasta.
Palermo
We also visited Palermo, the captivating capital of Sicily. With its rich history, stunning architecture, and vibrant culture, Palermo offers a perfect blend of ancient wonders and modern delights, making it a must-visit destination for travellers seeking an authentic experience.
My favourite sights were the Teatro Massimo, Fontana Pretoria, Palermo’s Cathedral, and the gardens of Villa Bonanno. I was struck by the beauty of palm trees, renaissance sculptures, and gothic architecture, which contrasted with the crumbling state of most townhouses. It was very busy, hot, but also full of energy. We got delicious arancini balls at Ke Palle on Via Maqueda.
Taormina
Last but not least, we stopped by Taormina for a couple of hours, which was just enough to get seduced by this glamorous and picturesque town, perched on a hilltop overlooking the coast. We wandered on the main street, Corso Umberto, chilled in the refreshing and majestic communal gardens (Villa Communale), and admired the breathtaking sea views from Belvedere di Via Pirandello. You can also visit the Ancient Greek Theatre of Taormina, which we skipped because of the line and lack of time. It was overall gorgeous, albeit on the pricier end of the spectrum.
Conclusion
This road trip itinerary has provided a comprehensive guide to discovering Italy within two weeks, including Cinque Terre, Florence, Rome, the Amalfi Coast, and Sicily. Our favourite discovery was Scalea and the surrounding villages in the Southern region of Calabria, a true paradise still untouched and unknown by foreigners. Sicily was very hot and tranquil, the perfect gate-away for a relaxing holiday. Cinque Terre and the Amalfi Coast offered, without surprise, some of the busiest destinations but also some of the most breathtaking sea views. The highlight of this trip was, without a doubt, the boat tour of the Amalfi Coast.
You can, of course, alter this itinerary based on your needs and wishes. You could add, for example, the cities of Milano, Venice, Bologna, and Napoli, the island of Sardinia, as well as the marvellous region of Puglia. If you have any questions or feedback, please don’t hesitate to get in touch!
Itinerary
You can freely save, edit, and download the following itinerary on Google Maps. It includes all towns, cultural and historical sites, restaurants, hotels, shops, and beaches mentioned in this article.
