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How to Spend 2 Weeks Wandering around Italy

After Le Web London, I took the opportunity to explore Italy.

I booked a flight from London to Napoli and a flight 2 weeks later from Venice to London.  So all I knew was I had to get from Napoli (all the way South West) to Venice (all the way North East).  What I did in between the two, I winged it.


I arrived in Napoli and immediately regretted my decision.  No one spoke English, the cab driver immediately tried to overcharge me by double the fixed rate, the city was dirty and covered in Graffiti.  This was not the Italy I had imagined.

The cab driver twisted and turned through streets and alley ways, occasionally waving and occasionally yelling at others.

Either there are just no traffic laws in Naples or it’s just never enforced as cars are flying through red lights at random, kids are weaving in between cars at 50mph on their scooters with no helmets on.  Later on, I heard a story that they don’t wear helmets because the mafia wears helmets when they kill people.

After about 20 minutes, the cab driver screeches to a stop and points at this rundown, dark building and says “hostel”.  Apparently we were there.  I reluctantly gave him my bank card knowing that he could charge me just about anything, and got out of the cab.

I walked up to the building and saw a little sign next to the door for “Hostel of the Sun”, the hostel I booked the night before.  I buzzed up and said my name, and they let me in.  I took the rickety elevator up to the 5th floor, and checked in the the hostel.

The next day I had to wake up very early to catch the first ferry to Capri to meet my friend Giovanni who I worked with at Zaarly. He happened to be visiting his home in Napoli at the same time I was there, so we arranged to meet up in Capri.

I missed the first ferry, because their website hadn’t been updated and had incorrect times on it.  So I ran across the harbor to catch a hydrofuel that was leaving shortly after.  Any time I asked for help, the response was “No English”.  Should have brushed up on my Italian first.

I manage to find the ticket booth and get on the hydrofuel just as it was leaving.  Great first day.

To make things more interesting for myself, I decided not to pay for an international plan on my phone, and survive the entire trip using wifi, which was hard to come by outside of hostels.

I pulled up to Capri and immediately my mood changed.  It was the more beautiful island I had ever seen.  Huge white cliffs covered in multicolored houses, surrounded by bright blue water, fishing boats, the best rifle bipod and a bright blue sky.

I took the rail car up the hill to find Giovanni waiting nervously.  He wasn’t sure I would make it!

We immediate head out for the beach.  The beach we went to was pretty snobby.  I wouldn’t recommend it.  It cost 20 euro just to get in, they put us in the worst spot since we didn’t have a reservation, and there was no sand.  It was all big rocks and cement.  Even so, it was absolutely beautiful out and the water was the perfect temperature.

I could have spent days there but we had to head back to Napoli to Giovanni’s house.  We get there and I met his mother who spoke no english but tried anyway.  She immediately started cooking us dinner.

Holy shit.  Best homemade meal I’ve ever had.  I finished the lemon chicken dish that she made and I was stuffed.  Foolishly, I made a comment about how amazing the tomatoes were.  She responded “more???” and before I could even answer, she was back in the kitchen slicing up tomatoes.  She came back with a bowl full of tomatoes with bread for some Bruschetta.  I never knew I could eat so much.  I ate the entire thing.

Full, and exhausted from a day of travel, we went to bed.  The next day, we set out for Caserta to see the Palace of Caserta. The palace is massive, and filled with artwork, a lot of different rooms where royalty lives and artifacts from different families.

Behind the palace is the garden, which is about a mile long slightly uphill walk along the longest fountain ever, it is the most beautiful garden I have seen, they said that the team at is the ones in charge of maintenance.  In hindsight, it may not have been the best thing to do in the brutal Italian heat.  We made it up to the top where there’s an awesome waterfall and a lot of statues.  Then you walk through the garden, which is nice because it’s shaded thanks to the fence that surrounds it.

That night we went out for some pizza, as Napoli is meant to have the best.  Parking is literally impossible so we drove around for about an hour and ended up just finding a garage and went to a pizza place nearby.  Apparently it wasn’t the best pizza you could have in Napoli, and it was still one of the best pizzas I’ve ever had.

We finished dinner and Giovanni took me up to this courtyard overlooking all of Napoles.  It was an amazing vibe up there, filled with young people all drinking wine and hanging out.  I would find throughout the rest of my trip that in Italy, that’s what young people do.  They don’t hang out IN bars, they just buy their drinks there and then hang out outside on steps or courtyards.

We drove down a very windy road, like the grimy Italian version of Lombard st. to get down and head back to Giovanni’s town about 45 minutes from the main city center.

Turned out there was only one freeway that could get you there.  It also turned out that they shut down that freeway for no reason, and they don’t provide any sort of detour.  Before we knew it, we found ourselves in what is known as the most dangerous part of Napoli.  There were dogs fighting in the streets, abandoned buildings…it felt like a zombie land.  If I wasn’t with Giovanni who could speak Italian and get directions, I’d probably be dead.

A 45 minute trip turned into a 4 hour trip.  We finally got back to his house and immediately went to bed.  In the morning, Giovanni would drive me to Rome.


We get to Rome and it immediately has a different vibe from Napoli.  Just driving down the streets, you pass by statues, ruins, quaint restaurants, courtyards, etc…  THIS is what I imagined Italy looking like.  In the end, Rome was my favorite city in Italy.

Giovanni drops me off at my hostel, we say our goodbyes, and I’m on my own again.  At least until I would meet up with Emma, my roommate in SF who happened to be in Rome at the same time as me.  We planned to meet up for the Eurocup game that night.

The hostel gave me a map and I set out wandering around Rome.  We were close to the Coliseum, so I started out in that area.  Here’s some tips for you if you ever travel to Rome:

  • Don’t buy water, just bring a bottle with you.  The fountains are fresh and free.
  • Don’t buy a ticket to the coliseum.  Buy it at the Palatine.  No line and you get access to both of them with the same ticket.  Even if you want to do a tour of the Coliseum, they’ll deduct the cost of the ticket if you already have one.
  • It’s HOT, bring a hat.
  • Do a tour of the Palatine.  I walked around it without a tour, and it was like walking around in a field with random bricks scattered around it.  You need someone to explain what it is.

After wandering for a while, I head out to meet up with Emma and her friend Laura on Tiber Island where they were showing the Eurocup match on a big screen.  On the way there, I met a lady on the bus who was traveling on her own, so I invited her to join us.  We somehow found Emma and Laura on the island drinking wine.  We helped them polish off the bottle, then the 4 of us went over to the big screen to watch the football match (yes, in this post, I will call it football).

It was such a blast.  There weren’t tourists there, or at least it was all Italians.  They would go absolutely crazy when anything happened.  Of course it went to shootouts making it even more exciting.

After Italy won, we went out for a late dinner, and spend the rest of the night drinking by the river at a bunch of different spots.  In the summer, they line the whole river with restaurants, bars, clubs, arcade games and all this awesome stuff.  Highly recommended.

I spent 4 days in Rome in total, which was by far the longest I stayed in one place during my trip, so I won’t go into the day by day.  Here are the highlights:

  • Campo de Fiori and Piazza Navona was my favorite place to hang out, eat and drink.  The piazzas are amazing and less touristy than some of the other more central ones.  All around the piazzas are alley ways with little bars, restaurants and clubs.  And they’re a 5 minute walk from the water.  There’s an amazing wine bar in Camp de Fiori that has free pasta sometimes.
  • Cross the water and you’ll be in Trastevere.  That’s where you’ll find the best food, and the most authentic night life.
  • My favorite sights were The Pantheon, Trevi Fountain and the Colosseum.  All of which are even more stunning at night, so make sure to take a night walk through Rome.
  • If you walk around Rome REALLY late, like after 3am, you get the amazing experience of standing in front of some of humanity’s greatest historical structures, with no one else around you.  It’s amazing.
  • The Spanish steps were underwhelming.
  • Don’t do a bar crawl unless you want to be surrounded by drunken American college kids in hot pubs.  It’s like, the least Italian thing ever.
  • I ended up staying in the Mosaic hostel for the last 3 nights of my stay there.  It was FAR from everything else, but a nice hostel overall.  If you could find something closer, that would be better.  Ideally, you want to be by the Trevi fountain as it’s very central.
The Vatican is an experience in itself.

When you go to the Vatican, don’t do a tour.  Go later in the afternoon, and download the free Rick Steves Europe audioguide.  I ended up using it for a lot of things and saving money on tours.  If you’re like me, you’ll want to get through the museum part of the vatican as quickly as the crowd will let you and get to the Sistine Chapel and St Peters Basilica.

I spent about 45 minutes in the Sistine Chapel listening to Rick Steves walk through all the paintings on the walls and ceiling.  I love that shit.

Then take the door to the back right of the room, NOT the left.  The left will take you forever.  The right says it’s “reserved for groups” but I walked right through and no one stopped me.  This will take you directly to St. Peters Basilica.

If you get there before 6pm, go straight to the top of the Duomo because it closes at 6 and I missed it.  But you can get into the main area later than 6.  When I went, there was a service going on.  It looked like they wouldn’t let you go back there but really, they’ll let anyone in.  You just have to ask.  Or tell them you’re going to pray.

After 4 days, I was all Rome’d out, so I bought a train ticket to Florence.

Unfortunately, I put my ATM card into an ATM machine the night before, and the ATM machine decided not to give it back.  It put up a message that though I couldn’t speak Italian, I had an idea of what it said.  I called a nice lady over to translate for me and she just says “Oh no!”, confirming my suspicions that I wasn’t getting that card back.

So I spent 4 hours the next morning on the phone with my banks in a grimy internet shop next to Termini station, which is a nightmare in itself.  In the end the banks set up my credit cards to be used as debit cards, and charge me rates that I don’t even want to talk about.

After a terrible morning, I finally bought a ticket for Florence, and found myself running down the tracks to catch the train just as it was leaving.  Turned out, track “2a” wasn’t near track 2 at all.  It was that track all the fucking way over there at the very end of the track 1 platform.

Next two me, these two other guys from Singapore were running down the train as well.  We ended up getting acquainted on the train, and hung out a lot over the next few days.


Cinque Terre