In June 2024, my husband and I took a trip to Italy to celebrate our 30th anniversary. We had hoped to mark our 25th anniversary with a proper trip, but family obligations and the illnesses and losses of aging parents made that impossible. By the time our 30th rolled around, we felt it was finally time to take a trip that made up for it. We weren’t exactly sure where we wanted to go, but a friend had recently taken a trip to Italy, and I was intrigued by her experience. Italy was always on my list, so I began researching to see if we could make it happen. We crunched some numbers and decided that it was doable, and I had the green light to start planning.
I was very excited as this was our first big European trip to somewhere other than Poland. I had started looking at vacation packages but realized they wouldn’t give me the experience I was looking for, so I began doing my own research. We only had 10 days to work with due to my teaching schedule, so I had to make each day count.
I’m the kind of person who thrives near water, so I knew we had to stay somewhere with great views of the ocean or harbour, no matter what. I knew I wanted to see Capri, Vesuvius and Pompeii, and the Amalfi Coast. I decided to make Napoli our base for four days with plans for day tripping, three nights in Positano and a final night in Rome. While we could have done the same day trips from Positano, it made more sense to stay in Naples at a lower per-night rate, especially since we would be out exploring all day and not spending much time in or around the hotel. One thing that was non-negotiable was that I had to have a balcony in Positano. Of course, this meant that we were looking at more expensive hotel options, but I felt it was worth it for the experience.
By the end of February, I had completed all my research, and we were ready to book everything for our dates at the end of June. My plan was to fly to Rome, take the train to Naples, then hire a private driver to take us to Positano. It was a more costly option, but given the uncertainty around ferry and train schedules, I felt that we would ultimately save time and avoid frustration. Some of the hotels I had bookmarked were already sold out, so I had to make some adjustments to my plans. However, I think the final choices we made were perfect for us.
At the same time, I also booked our sightseeing tours to Capri, Pompeii, and Vesuvius, as well as a full-day boat excursion from Positano and a food tour in Naples. All of the trips were cancellable and would only be charged to a credit card a few days prior to the date of departure. It was comforting to know that everything was organized and settled, so we didn’t have to book anything at the last minute.
?Naples: Vibrant, Chaotic & Historic
When the day finally came, we were so excited. We flew from Toronto into Rome and arrived at approximately 9:00 a.m. local time. The lineup to go through customs was unbelievable. I’ve never seen a lineup as long as that one. It took us approximately an hour and a half to finally get through. Once we collected our baggage, we found a kiosk where we purchased train tickets to Naples. It was fairly easy to find the platform, and soon we were on our way to begin our Italian adventure.
Two hours later, we arrived in Napoli. From the train station, we took an Uber to our hotel, the Royal Continental. It is situated right on the water, directly across from Castel d’Ovo. The area along the harbour (via Partenope) is a pedestrian-friendly zone, with no cars allowed (buses and taxis, however, are permitted).
There were dozens of restaurants where you could dine al fresco along the street, and the area radiated charm. Across the street, several restaurants were nestled along the water, offering a perfect view of Vesuvius looming in the background (or “Big Bad Brother” as one of our waiters called him). During our four-day stay, we saw wedding photos being taken, a flash mob engagement proposal (she said yes!), and many couples taking selfies to capture the moment.
I know many people claim to dislike Napoli, citing the dirty streets and overwhelming amount of graffiti. But Naples is a whole vibe unto itself. I think staying along the waterfront made a difference – we were able to walk into the main attraction areas and return to a quieter, more captivating area at the end of the day.
Our first excursion was a food tour with Get Your Guide. There were three different groups, each consisting of about 8 to 10 people. The guide not only told us about the local cuisine but also about the local history. The tour took about 2/2.5 hours altogether, and we sampled food from 5 or 6 different vendors. There was so much delicious food that it felt impossible to try it all, but somehow, we managed to savour a bite of every delicacy. It was a great way to see the sights and to get a better understanding of the city’s history.
We found that, yes, Naples is chaotic and gritty, but also undeniably charming and full of contrasts. Ancient landmarks stand beside bold graffiti, while narrow streets decorated with colourful overhead banners are lined with local vendors, just steps away from the sleek retail shops of Via Toledo. It is a city filled with churches on nearly every corner, as well as shrines and murals dedicated Lionel Messi, who is revered by many as a modern-day patron saint of football. ??
The day trip to Pompeii and Vesuvius (through Viator) was the highlight of our trip to Naples for me. Pompeii was awe-inspiring. I found it hard to wrap my head around the fact that it had been a bustling city full of people, with stores, bakeries, and brothels (!). (Be warned that if you are travelling with children, there are a number of … ahem… phalluses along the streets, pointing towards the buildings where citizens could find a good time). It was surreal standing in the town centre with Vesuvius looming over the ruins in the distance. The idea that it could have incurred so much destruction and death was hard to comprehend.
After the tour of Pompeii, we had lunch at a little restaurant halfway up the mountain that was included in the package. We enjoyed pizza, of course, and left feeling satisfied and ready for the next leg of the tour – a hike up to the top of Big Bad Brother himself. The bus took us up to the base of the summit, and we were left to hike approximately 1 km up to the caldera. It was a bit strenuous as the elevation was on an incline all the way up, of course.
At the top, you can gaze into the centre of the caldera that once bubbled over with lava that caused the extinction of the city below. It was foggy on the day we were there, and we were disappointed that we were unable to see the magnificent views of the towns below, as promised. However, the fog slowly lifted, creating a dramatic unveiling of the landscape that stretched all the way to Napoli’s harbourfront. It was truly a remarkable sight.
The next day, we had planned to visit Capri, but an emergency had been declared on the island due to an issue with the mainland’s water supply. Tourists were banned for a few days, and as a result, our tour was cancelled. However, that allowed us to meander around Naples and visit places of interest that we might not have seen otherwise.
We took this opportunity to ride the funicular (a mountainside cable railway) to visit Castel Sant’Elmo, a medieval castle/fortress built in the 1200s, set upon Vomero Hill. While it is not an elaborate castle, it was interesting to wander through the building, and of course, the views were the big attraction. From the rooftop of the castle, you can clearly see the “Spaccanapoli” – the long, narrow street that divides the historic center of Naples in two.
After that, we took the funicular back down to the old city centre and started exploring. We visited the Cloister of Santa Chiara to see the beautifully tiled columns and benches in the courtyard, roamed down via San Gregorio, also known as “Christmas Alley” (and of course I bought some Christmas decorations!).
Sadly the next day our time in Naples came to an end. I left feeling there was still so much we could have explored, but I was very excited to be heading to our next destination – Positano!
Naples – Quick Links ?
?Hotel: Royal Continental Hotel Naples – waterfront hotel across from Castel d’Ovo
?Food Tour: Get Your Guide – Naples Street Food – history, culture, and local bites
? Excursions: Pompeii & Vesuvius Day Trip – ruins + hike up the volcano
?Views: Castel Sant’Elmo – panoramic look at Spaccanapoli and the city below
??Dining:
- Errico Porzio – made to order personal pizza (try the Kellala ?)
- Ciro ristorante – waterfront restaurant along the marina next to Castel d’Ovo, with views of Mount Vesuvius
- Zi Teresa – another waterfront restaurant situated next to the marina, in the shadow of Castel d’Ovo and partial view of Vesuvius
?Positano:
Romantic beauty & seaside charm
I hired a private car to take us to Positano as I had read about potential train strikes, bus delays, and ferry cancellations. In doing my research, I found that renting a car is not advisable due to the very tight, winding roads along the coast and a serious lack of parking in Positano. Taking the private car allowed us to appreciate the scenery along the way, and we were taken right to the door of our hotel – no need to walk up the multitude of stairs from the ferry dock with our luggage banging along cobblestone streets.
When we arrived from Naples, we stashed our luggage at the hotel and headed out to start exploring. We wandered down the hill, popping into little shops, stopping to read dinner menus as we passed by restaurants nestled into small courtyards, and took lots of pictures, making sure to capture the gorgeous pink bougainvillea canopy draped over the narrow pathways. Everything is so colourful and vibrant, and so very Italian. It felt like we were in a fairytale.
Once we got to the main beach area, it became a lot more crowded but not crowded enough to dissuade us from wandering along the shore to take it all in. We were hungry and finally settled on Caprici, which had a patio on one of the main side streets, facing the sea. I had a limoncello spritz and we shared a seafood platter. It was the perfect first meal in Positano!
After lunch, we slowly made our way back up to our hotel to see if we could get into our room a bit early. Thankfully, it was ready and we were able to rest a bit before setting out again.
Our hotel, Royal Prisco, was perfectly situated halfway up the hill with incredible panoramic views of the ocean, the beach and the dome of the Chiesa Santa Maria Assunta (Saint Mary Assunta Church). The boutique hotel has three floors, The lobby and stairways feature white marble floors and is tastefully decorated with local artworks.
The rooms are very comfortable and the upper two floors feature large terraces with panoramic ocean views. These also include breakfast delivered to your room, to be enjoyed on the balcony. The breakfast was quite generous, and included traditional eggs and bacon as well as continental-style fare.
The view was far and away the best part of our stay. We sat outside at breakfast, came back to the room before dinner to enjoy our own aperitivo time and then lingered on the terrace before heading to bed for the night. IN the mornings my husband was more than happy to relax and enjoy the view while I shopped for souvenirs and other overpriced delights. LOL
For dinner the first night, I had wanted to go to a restaurant with a view of the sea. I had tried to make a reservation with Lo Guarraccino, as it is set right into the cliff overlooking the water but I was unable to get through to them. We decided to just show up and see if they had any tables available. They were finally able to seat us after about half an hour, so it wasn’t much different from showing up to a busy restaurant in North America on a Friday night. Our table was adjacent to the terrace seats, so we still had a great view of the water. The vista was quite magical at night, with lights from the boats on the water twinkling like stars fallen to earth.
The food was equally captivating. I ordered the seafood pasta and was not disappointed. (Hubert ordered a chicken Caesar salad for dinner for most of the trip to Italy – don’t ask ?). It was full of clams, mussels, and calamari – all fresh from the sea – and sauteed with baby tomatoes over linguine. The flavours were incredible and probably the best seafood pasta I had on my trip. After dinner, we strolled along Spiaggia Grande (the main beach) and took in the view of cliffside buildings illuminated and reflected in the water. Positano truly is a romantic destination with incredible views both day and night.
The next day we did an all day boat excursion, and it was absolutely amazing. The boat was small, with only 12 people on board. It took us along the coast, from Positano to Amalfi and the scenery was stunning. The rugged rock formations, paired with the beautiful buildings carved into the hills, the bright turquoise water and the refreshing sea air made for an unforgettable day.
There was a one and a half hour stop in Amalfi, but it was soooo very crowded. The only thing I wanted to see there was the iconic Amalfi Cathedral. Once I got my photo of the church, we wandered through the streets until it was time to go back. After that, it was time for lunch at La Gavitella, a restaurant where Jennifer Lopez had visited the week before. (we felt like we too were celebrities after we found that out!). The food was divine, and definitely worthy of a movie star.
After lunch the captain took us to two different spots where we had the opportunity to swim in the cool turquoise water. One of the spots had a small grotto that you could swim into, which was a very cool experience. When we reboarded, the captain shared a bottle of limoncello with us, and oohh, boy was it good! Unfortunately, he said he gets it from a local producer who does not sell it outside of the area, so we would not be able to buy some to take home. Sad ?
That night we tried a restaurant that a couple from the boat tour had recommended to us. (I can’t remember the name – I wasn’t writing a travel blog at that time!). We had a reservation for 9 pm but ended up being half an hour late. Why? Google Maps decided to direct us to the restaurant through the back way, across alleys with myriad staircases – up and down, then up and down, and then up and down once more, before we finally found the place. The waiter was very accommodating and allowed us to be seated for dinner, but not before telling us we could have just walked all the way up the main road rather than taking the back way! ????
Our second day in Positano was a beach day. Instead of joining the masses on the main beach, we walked over to Fornillo beach which was both quieter and cheaper. We were able to rent two deck chairs for 40 euros, and could order drinks and snacks as well. The beaches are full of pebbles rather than sand, so you really do need to rent the loungers if you are going to stay for the day. The water was beautiful and clear, and I loved enjoying the scenery of the rugged coastline from the water. Hubert wasn’t terribly impressed, however, as he prefers the Cuban beaches.
That night we went back to the restaurant Lo Guarracino and they seemed to remember us. This time we were able to get a table on the terrace with a perfect view of the harbour. There were a couple of hiccups with our service but nothing that made our dining experience unpleasant. However, the waiter felt bad and brought us complimentary limoncello shots at the end of our meal. It was a lovely gesture and made our last night in Positano that much more special.
The next morning, we enjoyed one last breakfast on the terrace before we left for Napoli.
? Positano – Quick Links
? Hotel: Royal Prisco – boutique hotel with terraces overlooking the sea
?? Boat Tour: Positano Small-Group Excursion – Amalfi coast + grotto swim stops
?? Beach: Fornillo Beach – quieter alternative to the main beach
?? Dining: Lo Guarracino – cliffside seafood with a view, La Gavitella – seaside lunch stop
?Rome in 24 hours:
The Eternal City Sprint
Our driver dropped us off at the train station in Naples and we took the train into Rome. We arrived just before noon, and dropped our luggage off at the hotel. I booked the Best Western Universo, which is only a 5-minute walk from the train station. However, this hotel was not like any Best Western you’ve ever stayed at in North America. It was full of white marble, and elegant details, and the biggest breakfast buffet I’ve ever seen.
However, I digress. Since we had less than 24 hours before our flight home, we had to make the most of it. So, out the door we headed to hit all the big attractions. I had plotted out the major sights that I wanted to see, and luckily most of them were within a 2 km radius from the hotel. We walked in one giant circle and were able to check off the Trevi Fountain (crowded, yes, but we still got some decent pics), the Spanish Steps, the Pantheon (I really wanted to go inside but the line up was quite long, and our time was very limited, so I definitely need to go back to see it), the ruins of the Roman Forum, the incredible and jaw dropping monument to Victor Emmanual, and of course the Colosseum.
I was so in awe of the Colosseum when I turned the corner and caught sight of it. Much like seeing the Eiffel Tower for the first time – monuments you’ve seen on television, in movies and magazines and on social media – that when you do finally see them in person, they don’t even seem real.
The circuit took about four hours, and unfortunately that day the temperature had soared to about 40 degrees Celsius. We had tried to enjoy a gelato but it had started to melt immediately and we ended up making a mess! By the time we got back to the hotel we were both exhausted and had to have a little rest to refresh before dinner. Neither of us had much energy left at that point, so we decided to have dinner close to the hotel.
I had scoured Google maps for well rated restaurants nearby and found a lovely little trattoria down the street. It was fairly small, and there was a wait for tables outside, but there was one table for two inside, situated right near the wide open doorway, so it felt like we were on the patio anyway. We ordered a classic caci e pepi, and tiramisu for dessert. It was perfect.
While I had hoped to explore a bit more after dinner, we decided to go back to rest and start packing up for our return flight the next day. In the morning, we hopped on the train to the airport and bid Rome arrivederci. On the flight home, we sat next to a couple who were returning from their 25th trip to Italy. They had no Italian heritage—just a deep love of the country that kept drawing them back. It made me realize that we had only just scratched the surface of what Italy has to offer, there are still so many regions I’d love to explore. One thing is certain: it may have been our first trip to this beautiful country, but certainly will not be our last.
Alla prossima, Italia!
? Rome – Quick Links
? Hotel: Best Western Universo – elegant, central, walkable from Termini (train station)
? Must-Sees: Trevi Fountain, Spanish Steps, Pantheon, Roman Forum, Colosseum
?? Dining: Trattoria Cecio – authentic Roman fare (cacio e pepe + tiramisu)
?? Google Map: Rome Highlights
? Spotify playlist: Italian Summer Vacation
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