Backpacking Italy


Jonathan Wong / October 24, 2019

7 min read––– views

Cinque Terre

It all starts with a cheap flight.

Back in May, I was browsing flights to Europe hoping to plan a vacation for the fall. Originally thinking Greece, I managed to notice a cheap flight from Des Moines to Venice. It seemed too good to be true.

My fiancée and I decided to pull the trigger after realizing how many unused credit card reward points we had. There were only 4 seats left, so we quickly scrambled to grab our passports and fill out the information. We'd be starting and ending in Venice - the rest we would figure out later. A few minutes later, it was finalized.

We were going to Italy! 🇮🇹

Why Backpacking?#

I love minimalism, especially in regards to traveling. Lugging around two checked bags and a carry-on is expensive and often unnecessary. Plus, we knew we'd be going from planes to trains and doing a decent amount of walking.

We had heard good things about Tom Bihn's Aeronaut 45 backpack from a friend. It's the maximum carry-on size most airlines accept and is very versatile. It can be worn as a backpack or carried like a bag. There are ample pockets and containers to organize and store your belongings. It was a perfect match.

We were able to fit 10 days of clothes, shoes, toiletries, and photography gear into our respective bags with ease. The backpack straps were comfortable enough to support long walks. Overall, I would highly recommend this bag for others considering downsizing their luggage.


After a pretty seamless overnight flight connecting through Chicago, we arrived in Venice in the morning. This might be an unpopular opinion, but I love airplane food on international flights. It could be the lack of other options, but it always hits the spot 💯

Shortly after landing, we got some euros out of the ATM (*bancomat) and caught a bus to Venezia Mestre. Our Airbnb was only a few blocks from the Mestre train station. We chose to stay outside of the main city center to avoid some of the tourists and get a cheaper rate. Traveling into the city via train was fairly simple, even for unexperienced train passengers.

Mestre to Venice Train

Venice's gritty landscape, unique alleyways, and water taxis were charming. However, even outside the busy summer months, it was still very touristy. We nabbed some fresh pizza and spent the rest of the afternoon exploring the canals.

Venice, Italy

Some parts of Venice were very dirty and using the public restroom was not an enjoyable experience. I wouldn't recommend more than a few days in Venice - but I'm glad we saw it.

Cinqué Terre#

We rose early the next morning to catch a series of trains to Manarola. We went through Florence and La Spezia before finally arriving in Manarola. It took about 4 hours in total.

The Trenitalia trails with designated seats were excellent. We sat back, relaxed, and took in the countryside. The regional trains... not so much. We were packed like sardines on the two-hour leg from Florence to La Spezia. Alas, we arrived in Manarola with the afternoon ahead of us.

We trekked up and down the steep city streets searching for a place to eat. After eating the most amazing pesto gnocchi I've ever had (seriously), we grabbed two cones of fresh gelato across the street.


The laid-back pace of Manarola was more of the vibe we were looking for. The city by the sea had exquisite character, from the small gift shops to the unique houses airing their laundry out to dry on the balcony. Having a few drinks didn't hurt, either.


That night, we both struggled to sleep. Our sleep schedule still hadn't caught up from the 7-hour time change. The next morning we rose early and went on a brisk hike up the mountain-side for a better view of the city. The crisp ocean air, sunny skies, and 70-degree weather made it worth the steep incline.

To cool off from the hike, we took a brisk dip in the Mediterranean Sea. It wasn't exactly warm.

Swimming at Manarola

One of the highlights of the trip was the unbelievable sunset we witnessed.

Cinque Terre Sunset

When I look back on Cinqué Terre, I'll remember a few things: pesto gnocchi, chocolate chip gelato, and the amazing views.


Our next destination was the Almafi Coast, but we wanted to break up the travel day to be a bit shorter. We decided to stop for a quick night in Naples before heading out early for the Almafi Coast.

Naples is the 3rd largest city in Italy. I can't really summarize the entire city in our short time there, but our experience was pretty average. Highlights include excellent pizza, great wine, and a short walk to the train station. Everything else was pretty lackluster. There are definitely some sketchy areas and questionable people. I'm not sure it's fair to judge the entire city based on this, but I'm not sure I would recommend it.

While in Naples, we met up with our two friends Clare and Liz. They joined us for our stay in Praiano.

Praiano (Almafi Coast)#

The Almafi Coast consists of a handful of towns, but the most famous by far is Positano. You've probably seen a picture similar to this before. It's iconic.

Positano, Italy

Our decision to stay in Praiano over Positano was mostly based on cost. An added bonus of this was being just far away from the main tourist areas. At night, we sat on our balcony and listened to the ocean in silence. It was beautiful.

One of the best decisions we made was to hire a private transfer from Naples to Praiano. There isn't really a direct route to Praiano or Positano. We could have also taken the train into Sorrento and then got a transfer or taken the water taxi. But why bother? Our driver was prompt and did an excellent job of navigating the tight, windy roads and erratic drivers. Renting a car would have been an expensive mistake. I would highly recommend Daytrip - it's what we used.

Groceries and restaurants were a short walk away (but with steep inclines, ouch). The grocery stores were very affordable in Praiano, especially splitting between the four of us.

I'd highly recommend getting out on the water if you can. We did a boat tour out to the island of Capri, which was fantastic.

On a boat in Positano, Italy

Capri, Italy

Quick Tips#

If you're planning to head to Italy, here's a few things you should know (plus some general travel tips):

  • Keep tabs on flights and track prices.
  • Ideally, book your lodging months in advance for the best rates. I'd suggest a mix of Airbnb/Hotels depending on the location.
  • Make sure you get an outlet converter.
  • Electricity in Italy conforms to the European standard of 220V to 230V, with a frequency of 50Hz. Don't plug an electric razor in without checking if it's dual-voltage 😲
  • If you haven't already, consider getting TSA Precheck / Global Entry.
  • Ensure your credit card doesn't have international fees.
  • I would recommend taking out some euros ahead of time or at the airport. There will be places that don't accept a credit card.
  • Use Google Translate and download Italian offline, in case of spotty coverage.
  • If you use Spotify, consider downloading some playlists offline as well.
  • Check into your flight as early as possible!
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