Venice is literally sinking into the sea. There’s a flooding season now, in autumn, where impromptu infrastructure appears stacked in the form of catwalks and bridges stacked near low-lying areas. When the tide comes in, water flows up through the cracks of St Mark’s square at the same time as it pours from the sky. Venice, a completely unique city, is slowly disappearing. It may be the most endangered city in the world – and among the most visited. I don’t know how long it will exist in it’s present form before both deluges overwhelm it: the water, and the tourists.

I’ve been interested in Venice, for some time and for a variety of reasons. The fact that it’s a pretty city makes it appealing – but also the peculiar history (I’d been interested since reading Empires of the Sea). And – I’d heard wildly divergent opinions. Some people said it was their favorite city in Italy; others, that it barely rated two days. My opinion, at the end, was split. You’ll see why.

We woke up early in Verona, grabbed some snacks, wrestled with the coffee percolator (and lost), and left our lodgings. Before going to the train station, we stopped on the far side of the Arena, away from the Piazza Bra, at a small coffeeshop. Here, we were forced to acknowledge that we had no idea how to order a black coffee in Italy. Walk into a coffeshop and ask for a ‘caffè,’ the Italian word for ‘coffee,’ and you’ll get an espresso. Frankly, this is more my speed than drinking an entire cup of coffee, so I enjoyed the opportunity to get a little jolt of energy. Now in a civilized mood, we continued to the train station.

From Verona to Venice is about an hour and a half by train. We shared a table with an older Italian couple who clutched pre-made vending machine sandwiches for the entire trip. I couldn’t believe how much they talked. Or at least, how much the wife talked, the man grunted. We dozed off on the train for a bit, and I only woke up as we started crossing the bridge to Venice.

Venice is the only major post-Roman city in Italy; it was formed after the fall of the empire, when locals grew tired of being raided by semi-nomadic tribes. In an effort to escape, they filled in parts of a local lagoon and formed a man-made archipelago city (there are officially seven islands). For a long time, the only connection with the mainland was by ferry, something that made self-defense easy. Now, of course, so many people visit that there’s a thin curving bridge into the city. One island has a small area for parking, but besides that, it’s a city devoid of cars, which is awfully liberating: it feels more human. Plus, you can wander where you want without paying any mind to traffic.

Getting out of the train station, we grabbed a city-tourist discount card which gave us unlimited trips on the local metro service for 76 hours. Rather than subways, buses or light rail, the metro in Venice is composed solely of ferries that cruise up and down the canals and around the islands. We’d take full advantage of these trips during our stay.

Our first mission was to get to our AirBnB host. Rushing through the narrow streets, we grabbed a huge rope of licorice and made it to our lodgings in time for checkin.

For the entire trip, we stayed with AirBnB. I’ve stayed with AirBnB hosts for many trips now. It’s cheaper than hotels, often more convenient, and feels more “authentic” (though hosts in Italy were more professional than in other countries). However, there’s one major downside: that AirBnB requires scheduling a meeting time with your host. You can check into a hotel at any point, but you check into AirBnB at one time. So, your schedule is more locked in than with other options. In this case, we were expected in Venice in at 1pm, so our schedule had to conform to that time.

Venice is notorious for its confusing streets and the fact that it’s easy to get lost. Thankfully, we could compose a route to our host with only a single turn from the Rialto Bridge ferry stop, though this was somewhat roundabout. The location was superb, however, just 5 minutes from St Mark’s Square and 10 minutes from the Rialto Bridge, it was in striking distance of all the major sights.

We’d be staying for two nights. The rooms were plush and there was a luxurious roof balcony. It would have been a great place to hang out, except that in November was just too cold and windy.

Backpacks dropped off and settled in, we headed out to wander the streets. That’s really the best part of Venice – all the alleys and nooks and crannies hiding shops, apartments, and churches. At the end of our stay, I tried to reconstruct our route, tracing out the broad strokes, but the city is great for getting lost in, because you can never get *too* lost. You’re on an artificial island, after all. Mid-wander, we found a restaurant, dined on gnocchi and ravioli and wine, then found a supermarket (Coop, a popular Italian chain) and got really cheap wine. At this point, the weather finally made up its mind and started to rain, so we hurried back to the apartment to nap wait for clearer skies.

The rain let up at 11 that night, and we headed out for our second round on the town. Another wander, this time a great arc northwest around the islands to return to the railway station, from which we caught a late-night boat back to the Rialto bridge, then headed to St Mark’s.

It was flooded. We’d seen a bit of water earlier, during the rain, but the fact is: during the fall, St Mark’s floods, to depths of over a foot in some places. The local police put out elevated boards just wide enough to fit two people, and you can thread your way across the low-lying areas this way. It’s great fun.

At this hour (somewhat after midnight), and given the rain earlier, there weren’t many people out. It was beautifully secluded, calm, not too chilly. During summer days this is one of the most crowded places in the world, but we had it almost to ourselves. I felt mesmerized by the place: St Mark’s has four prominent features: St Mark’s Basilica, which we would visit the following day; the massive sculpted entrance of the Doge’s Palace (we’d also visit this); the campanile or bell-tower; and what could be termed the arcade, or the gallery of super-high-end shops that surrounds the square.

The square forms a rough L-shape, and when we first stumbled on it (in daytime), it took me a long time to come to terms with the layout – it was a case where my mental composition of photographs was totally distinct from the reality of the place. Nonetheless, I grew to like it, and we were lucky to see it so empty when the power wasn’t dissipated by swarms of tourists.

We finally made it back to our AirBnB apartment around 2 in the morning. I carried a pedometer through the trip, and we registered 12.6 miles of walking over the course of the day.

It felt like a very long day – leaving from NYC at 8pm on Saturday, arriving in Milan at 11am, seeing the sights there, then heading into Verona. From Milan to Verona is a 2-hour train trip, so to recharge for the rest of this 48-hour “day” (neither Alex nor I slept much on the plane), we took a quick nap on the train.

Outside the train, the northern Italian scenery was beautiful. In one area, the hillsides were scarred and chewed away; I think these were granite mines. Later, we zoomed past Lake Garda, the largest lake in Italy. But mostly, we slept.

Verona is a surprisingly large city (250,000 people – it feels smaller), but not one of the A-list tourist cities. Mostly, it’s known as the legendary home of Romeo and Juliet. You can see a modern balcony that an enterprising local named “Juliet’s Balcony;” there’s a museum nearby. A lot of tour groups visit this on the trip between Milan and Venice, and skip the rest of the town. We saw the rest of town and skipped the balcony. Curiously, one of Verona’s sister cities is Albany, NY and seeing the Albany coat of arms plastered on a government building near the center was jarring.

There’s some other nice attractions though – notably a mostly intact Roman arena and two nice piazzas.

We woke up as the train pulled into the city. Or rather, pulled nearby the city. We had to traverse an off-map gap between the railway station and city center, but luckily we were able to find the right direction by guesswork, and it was nearly a straight shot along a main street into the charming Piazza Bra.

Rain was just letting up as we pulled in, and as we walked up the main street, a rainbow came out above the old city gates as if to thank us for visiting. The weather held out the rest of the night, too.

A custom we saw in many of these Italian cities is the passagiata, when townspeople head out and walk the town, and they were all headed to the Piazza Bra. A large square (technically, a triangle), the Piazza is shut to traffic. In the center is a small park filled with diverse trees and statues; along one border are civic buildings and along the other are restaurants with open awnings and gas-torch heating. The third side of the square is formed by the arena.

The Verona Arena was built in 30 AD, and was a precursor to the Colosseum. It’s much better preserved than the Colosseum, due in large part to the simplicity of its construction (and I suppose, because the Vatican wasn’t mining it for marble). It’s still used these days for public concerts, and there’s a nice view of nearby Piazza Bra from the top. The Arena was mostly empty, with just a few tourists wandering around, in sharp contrast to the crowds milling around outside. We could see people walking their dogs, families strolling with baby carriages, and people grabbing dinner. From the time we set foot in the Arena, to when we left about half an hour later, the sky went from dusk to dark.

Leaving the Arena, we had an appointment for our first AirBnB reservation, on the far side the Adige, the river that encircles much of the old town. On the way, we passed some sort of party or business grand opening – it was hard to tell. We stepped inside and snacked on some free dried kiwi and hard cider. I like the way in which Italian bars and drinking spills out on the streets, as if including everyone in the festivities. It felt much more communal than in the US, oftentimes near more popular nightlife, we’d see crowds spread halfway across the street.

Passing by this, and crossing the river, we walked a few blocks to the reservation. This was a ‘full apartment,’ though really it ended up being a tiny studio. That was fine, it was cute, warm, and had plenty of amenities. The only downside was a very weak shower that barely reached lukewarm. Dropping off our bags and unpacking a little, we drank some water, had some snacks, and then headed back out to explore the town.

Mostly, we wanted to eat. There was a pizzeria nearby, recommended by both our host and Rick Steves. But here we were faced with another reality of Italy – that we were ready to eat dinner a lot earlier than the Italians. In fact, most restaurants were closed from 3:30 to 7:30, so we were often the very first customers. In this case, though, we were too early and the pizzeria wasn’t open yet.

So, we headed out to do a loop around town. We started by crossing back to the old town, then headed north along the Adige – a treacherously fast-running river. We dipped in towards town, wandered partway across a footbridge and through a charming little medieval area. We passed by the Duomo, a moderately large 850-year old church, where Sunday evening mass was in session. We stood in the back and silently watched mass until it let out; some older guy came up and shook our hands. I think we were the youngest people there. Afterwards, we wandered in the direction of the old town, and another nearby church was letting out, so we followed the crowd past nearby shops, and then continued onwards to check out the city’s castle (nice enough). We were getting pretty hungry by that point, so we made a beeline back towards pizza.

But – we stumbled on a road where the entire center was cut out, revealing Roman foundations underneath; this was near a roman gate embedded in a nearby building, the Porta Leoni, so called because it’s decorated with two lions. After that, it was straight for pizza.

But – there was a half-hour wait for the pizza. Luckily, the pizza place was next to a bar, so we grabbed two glasses of mediocre wine. The pizzeria waitress somehow figured out where we were and grabbed us (“oh yes, the foreigners”), as our reservation was ready a bit early. I ordered an egg & asparagus pizza; Alex had Buffalo Mozzarella. The pizza was good – crusts were uniformly excellent in Italy – and the wine was cheap (usually $5 for half a liter, $10 for a liter). The place was packed with locals, and we had bizarre plexiglass tables filled with bent up silverware. It was a great start to the trip. Bloated with tasty food and wine, we headed back to the apartment for some long over-due sleep. We’d get up early the following morning to head to our next destination: Venice.

We wanted to travel – but where? Alex and I had been carefully hoarding our vacation days all year, but now it was early summer, we had to decide where to go. The whole world was open to us for two weeks.

My own criteria were simple: somewhere we wouldn’t need a car, and somewhere not in Northern Europe or America. After all, over the past three years, I’d traveled to Iceland, Belgium, the Netherlands, and Germany, and driven across much of the US. It was time for a change. Alex’s criteria were equally straightforward: somewhere outside of South America. Having traveled to Mexico in the past, she wanted to see something more exotic… and maybe even cross the Atlantic.

These were broad criteria, leaving the vast majority of the world to choose from. We had to develop some heuristic to limit the options. With only two weeks available, the major constraining factor was time. That eliminated Asia and much of Oceania. You don’t want to spend 16 hours flying back and forth all the way around the world, and then be so jetlagged you can’t do anything. I’ve worked with many people who have families in India, and by and large, they guard their vacation days even more jealously than I do, carefully scrounging together enough to disappear for a month. This simple decision eliminated half the world.

Next, we preferred somewhere with a reputation for safety, so decided to leave out much of Africa and the Middle East. Of course, I would love to visit eventually, but these aren’t a great place for novice tourists! Now, we selected areas with the most to do: England, Istanbul, and Italy were the top choices – and Italy won out because of the overwhelming amount of travel choices, the resources available, and the sheer convenience.

As time went on, and we assembled books and trawled websites, the options within Italy itself grew daunting. We composed a huge google doc with links, priorities, and notes. There’s a ridiculous amount to do in the country. Consider: seeing the snowcovered Alps and Suedtyrol; boating around Venice; strolling the Roman forums; traveling to the sunny isle of Capri; seeing the preserved remains of Pompei’i; sleeping in the ancient caves of Matera; traveling along the Mediterranean and seeing Sicily or the chain of interlocked villages in the Cinque Terre. Not to mention the microstates of the Vatican and San Marino, the artistic masterpieces of Florence, the hilly streets of Siena, and dozens of other little sites that dot the country.

We eventually settled on the following itinerary:

1. Milan – because the cheapest flights go there.
2. Verona – as a smaller stopping point before Venice.
3. Venice – because it looks damn cool.
4. Florence – because art.
5. ? – a two-night gap to go where we wanted.
6. Rome – because Rome.
7. Milan – to fly out again.

Now we just had to find the time. Alex was busy through November, so we were looking at that timeframe – and in September, cheap tickets popped up online: $500 round-trip to Milan. Done!

Tickets booked, it was a waiting game. We did more preparation, particularly at the end of October, booking rooms on AirBnB. But there’s only so much preparation you can do, and only so tightly you can schedule a trip. I prefer to select sites the day before I visit them, according to my mood, so that’s what we did here.

Finally, after an interminable wait, the day arrived. We wanted to travel light, not to worry about luggage, so I selected the least amount possible. This method of travel has served me well in the past. No possibility of lost bags, no standing out as a tourist, and no need to check into hotels early. Bag packed, I said goodbye to Miko (a neighbor would be watching her), and headed into Manhattan.

I’ve found little as liberating as stepping out of the apartment, with only a backpack, headed for another country. It feels like an inside joke, as I walk pst people who have no idea I’ll soon be on another continent.

I met Alex in the subways near Penn Station, and we headed towards JFK. Unfortunately, there were some construction problems with the line, and the train stopped somewhere that wasn’t JFK, so we ended up taking our first gypsy cab ride. I suppose it’s something you’ve gotta do if you live in NYC at some point, right?

The plane was delayed. Of course. There were no announcements and we ended up waiting an extra hour in the airport before we could board. And when the boarding officially began, everyone rushed to the woman checking the tickets, no queue or organization to be seen. The man next to us chuckled at our confusion (and our frustration with the delays). “These are typical Italians,” he laughed. He was, of course, Italian. I’ve found Italians, by and large, to be wonderfully self-deprecating and conscious of their stereotypical faults – namely, a lack of timeliness and a charmingly self-centered disorder.

The flight was 9 hours. We had a lot of wine and watched X-Men: Days of Future Past together, on the little seat-back screens. They fed us three times. It was good, insofar as a flight can be good (ok, it wasn’t the Singapore Airlines Suites).

Finally arriving in Milan, we made our way out of the airport. It’s 30 minutes to the center of Milan via commuter rail. The train departed from under the airport and headed to the center, surrounded by large banks that obstructed our view of the countryside. I could tell Alex was anxious to get a look outside; I was anxious for her to see Europe (and of course, to see Italy for myself). We got some hints of the countryside – large flat fields, the industrial side of towns, tiny little houses. It reminded me of parts of the Netherlands.

Finally we pulled into Milan. A city of 4 million, it’s the 7th largest city in the EU. Despite its size, it doesn’t have a lot of tourist sites: the Milan cathedral and Da Vinci’s Last Supper are the best known. The city has a business-like, no-nonsense air. Outside the tourist quarter, we found quite a few restaurants where nobody spoke English. It’s known as a financial and fashion hub, has wide streets, and as a result it felt a great deal like NYC to me. We only had a few hours before heading to Verona, but thankfully the few main sites are within a few blocks of each other (we returned briefly on our final day to see a bit more).

Literally two blocks from the train station (Milano Cadorna), and anchoring the city’s central park, is the huge Sforza Castle. There was some kind of book conference there – we got to see how Italian publishers sell their books (the same way American publishers do). Despite the fact that Milan isn’t very touristy, and this was the off-off-season, the castle was quite popular. You could wander inside and see the grounds, for free. There were several museums which we opted to skip, and a few tourist stands outside that we walked past. I liked the castle, which was forthright and square, and which must have been imposing in its day, but which now felt like a nice cultural hub of the city. On a tight schedule, our next goal was the Milan cathedral, which is a 15-minute walk via the main shopping street.

The entire area was packed, because Italy was playing their neighbor, Croatia, in a Euro Cup qualifying game (fireworks thrown on-field, riot squads, delays, 1-1 result). Lots of checkered red-and-white shirts, chanting, singing, drinking. Here was also where we met the most dreaded Italians: the hawkers. Clouds of these people, who aggressively shove flowers, selfie-sticks, bracelets, and other knick-knacks into your face, swirl around the tourist sites and even inside restaurants. Even the people handing out comedy club cards in Times Square aren’t so aggressive.

The cathedral, the largest in Italy, opens on a big square filled with Croatians. There was some kind of event here, complete with miniature net-covered soccer fields with 12-year-olds (they were bad). Thankfully, there was a short line for the cathedral, but we were faced with something new: soldiers checking the bags. At least, I think they were soldiers: they wore berets and camouflage, and seemed militant. The security was so severe that I felt like I was back in the US.

The Milan cathedral is among the nicest I’ve seen, and we spent some time wandering around the inside. The highlight, to me, was a statue near the front, a solemn, muscular man clutching a book and swathed in a cloak. I was entranced by this statue, but something was off… it took me a while to realize just what was wrong with it. The subject, Saint Bartholomew, was one of the twelve apostles, who was martyred by flaying. So, that was no cloak – it was his own skin. A chunk of Old Saint Bart’s skin ended up in San Bartolomeo all’Isola, a small church we took refuge in during a rain shower in Rome. In a sad irony, Saint Bartholomew became the patron saint of leather workers.

We wandered around the cathedral and found the line to go up to the roof (6 euros). The cathedral, right in front of us, was under repair. All the building restoration I saw in Italy was fronted with very classy facades around the scaffolding to obscure the construction. It was a thoughtful touch, except for the enormous animated Samsung ad in the middle.

On the roof, we wandered through a forest of ornamental spires, gargoyles and saints. The view of the city is refreshing, and you can see the Alps in the distance (we’d also gotten a tremendous birds-eye view on the flight in). There were some nooks and crannies that offered a refuge from the crowds. Not to mention, a huge volume of bizarre gargoyles. One of my take-aways from the trip overall is that my knowledge of Christian iconography is woefully underdeveloped. I’m sure there’s an incredible backstory behind many of these saints, but all I can see are funny poses. Any recommendations where to start?

After we came down from the roof of the cathedral, we took the subway to Milano Centrale, the central train station. Destination: Verona, for some much-needed rest and a night in a smaller city before heading to Venice.