Rome, Naples, Pompeii, Florence, Pisa, Venice

Italy is one of the top destinations on most people’s bucket lists. I had wanted to go for many years and finally made the trip in 2016. I planned a two-week solo holiday to some of the most popular cities and sites. Although I was curious about everything Italy had to offer, Pompeii was my must-see destination with its mysteries, legends, and rumors about curses.

It seems tourists who take even the smallest stolen artifacts experience bad luck for years after. Many tourists have mailed the stolen objects back with letters of apology and hope that their bad luck curse will be broken…

To truly experience Italy, one would have to visit many times for many years. However, I really wanted to see at least the highlights, the major sites, and the most unique places, and then in the future visit the more obscure locations.

DAY 1 – 4 Rome

Rome is a great place to start your Italian adventure. Offering so many wonderful tours, artworks, sites, dining, and day trips to nearby areas of interest. I recommend taking two days to see the city on foot or guided tour. The Colosseum, Trevi fountain, Roman Forum, Spanish steps, and the Vatican can all be seen in a matter of hours. However, if you want to see the Sistine chapel or enter some of the museums, you would need to buy tickets or maybe return on another day.

I always try to do a guided walking or shuttle tour and then return to spots that interest me. However, in Rome, my backpackers gave me a really good city map, and it was clear that so many points of interest were reasonably close together.

DAY 4 – Naples and Pompeii

Pompeii is 241 km or approx 2.5 hours drive from Rome. Check out websites like Viator to book your day trips to many places including Naples and Pompeii.

This trip started early in the morning and took us through the city of Naples with a short stop near the sea. Then on to the city of Pompeii where we had lunch and then to the archeological site where we spent many hours.

A tour guide took us on quite an extensive walk around the site and answered many questions. We also had time to take pictures and relax before the bus ride back to Rome.

DAY 5 Rome to Florence

Rome to Florence is 279 km or approx 3 hours by train. Traveling by train in Italy is very convenient, inexpensive, and safe. There are always staff or fellow travelers on hand who speak English so there is no need to worry about your rusty Italian.

I really enjoyed this trip as it’s interesting to see new sites and learn from an informed guide. But, it’s also great to meet other travelers. I learned a lot about the food and hot springs in Hungary from one man and about day to day life and traditions in Singapore from a business man and his son. This is one of the perks of day trips and inspires me to keep traveling.

DAY 5-7 Florence

There are a few train stations in Florence, but I believe most of the nice accommodations, shops, and old town are near Firenze Santa Maria Novella station. I was able to exit there and easily walked to my backpackers in 10 minutes. Past beautiful buildings, cobblestone streets, and luxury designer stores.

I had no idea what to expect in Florence, only that people I had met over the years, said it was their favorite Italian city. There is so much to see in Florence from the famous works of art, architecture, markets, and museums. However, what I remember most, was the friendliness of the locals, delicious cafe lattes on randomly found tiny patios, and seeing dogs march into shops with their owners instead of waiting outside.

Be sure to join a tour or get a good map and see the Cathedral of Sant Maria, Uffizi gallery, Accademia gallery (the David), Ponte Vecchio, Piazza della Signoria, Boboli gardens, and the Basilica of Santa Croce to name a few.

Florence also offers easy access to Pisa, ski trips to the many resorts nearby, and day trips to the famous Cinq Terre region. I planned enough time to visit Pisa but will have to return to do some skiing or experience these other incredible destinations.

DAY 8 Florence to Pisa

Pisa is 84 km or approx 1 hour from Florence. Once you exit the train station, you can easily walk through the city towards the leaning tower Piazza del Duomo location.

I’m sure the taxi ride would be short, but I highly recommend walking. I passed so many market stalls brimming with delicious candies or fresh chili peppers or vegetables, souvenir shops, or more upscale gift shops on cobblestone lanes.

I had no idea what to expect as most of the photos of Pisa only focus on the tower. however, there is an active massive church and quite a lot of green space to sit and take in the surroundings. If you’re interested, you can pay extra to enter the tower and go up to the top to look out. I didn’t but would consider this if/when I return with my son.

I spent quite a few hours in Pisa, drank a few coffees, and then returned to Florence for my last night.

DAY 9 Florence to Venice

Florence to Venice is 256 km and almost 3 hours. The train station is beautiful and exits on one side onto the famous canals. There I took a ferry to my backpackers which was on a little island directly across from the main tourist island.

I highly recommend my accommodations, Generator Venice on Giudecca island. Part of a chain of hostels, it is affordable with many options from female-only dorms to family rooms to singles. Clean, and nicely decorated with a large bar and restaurant/hang-out area on the first floor, it would a great choice on any budget.

Most incredibly, from my upper bunk, I had the most amazing views of the canals and the sparkly lights from the boats crossing the water late into the night or in the beauty of the early morning sun.

DAY 9 – 12 Venice

The next day, I grabbed a ferry to Venice island and spent hours enjoying the piazzas, discovering the tiny lanes, and posing on the bridges. I don’t know if I was just hungry, but I’ve never seen so many windows filled with decorative cakes and cookies, and pastries.

I should say that as I was traveling in December, Venice was very quiet which I understand is unheard of. I spent a lot of time just soaking in the scenery and trying my best to imagine what it would be like to be from such a place.

One evening while waiting for the ferry, I saw a young boy on a scooter almost go into the water near the ferry dock. He and his mother seemed utterly unfazed as I guess it’s not uncommon or that big deal if he did go in?

If you have taken gondola rides, walked, dined, or drank enough of Venice, there are many day tour options to the nearby islands of Murano, Burano, and Torcello. Here you will find handmade crafts including blown glass and lace, and ancient cathedrals and sites.

DAY 12 Venice to Rome

Venice to Rome is a 525 km approx 4.5- 5.5 hour trip depending on whether you drive or take the high-speed train. I took the train, to be honest, I don’t remember the journey being so long.

However, there was a lot of entertainment

I ended up next to an Italian family from New York with thick NYC accents and a bone to pick. One son was very quiet and stared out the window while the other was testy and sensitive to some events that had happened on the trip. It seems some local men had admired his mother’s beauty and he wasn’t having it.

He was irate about how wrong it was and what he would have done to those men if he had known sooner or had a good chance. His mother was equal parts flattered by her protector and also worried that her son was going to get them thrown into an Italian prison. The other brother only chimed in to shush or roll his eyes at his brother when he felt too many fellow train patrons staring at them.

DAY 12 – 14 Rome

Last days in Italy. You might just want to relax after so much travel, eat at your favorite restaurants, or maybe go and buy those souvenirs or items you had your eye on.

If that’s not you and you feel like another day trip, you are in luck! Wine tasting in Tuscany? Tivoli Day trip? Positano and Amalfi coast, Assisi and Orvieto, or Capri full-day tours? If not, there are pasta-making classes, food tours, or even try your hand at becoming a gladiator.

Say Addio! to Italy and start planning your return!

I really liked Italy. I had a really lovely experience and met so many friendly people. Although I ate at some really great vegan restaurants, there were so many more I wanted to try. I had no idea I would end up living in nearby Spain, so I hope in the future to spend more time in each city and region and take my time.

I could easily spend 5-10 days in each city, eating, taking in the sites, and hopping on a day trip every few days. As well, there are so many other regions like Puglia that I am excited to see. But, if you are looking for a perfect first visit to Italy then this itinerary will leave you feeling satisfied that you have seen some significant sites and inspired to discover more.

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