How Not to Lose a Guy or Girl in 10 Days in Italy

To anyone taking an Italy vacation with a significant other, the obvious tip I would offer is to refrain from watching Gone Girl on the plane. The stress on your relationship inherent to such a trip is worrisome enough without imagining what might happen if you really piss her off.

Our first fight happened on our second day in this romantic land, culminating with my fiancée crying in an uncomfortably conspicuous spot in St. Peter’s Square (where I presume the tears are usually reserved for the Pope rather than secular matters). Traveling overseas with an intimate partner demands teamwork, compromise and communication. Under some circumstances, it’s not a stretch to call the struggle a litmus test for how you two will fare in marriage.

Italy fits those circumstances because of the overwhelming quantity of sights and experiences to capture. If we were simply going to a beach destination or on a tidy self-contained tour, there would not be as many challenges with logistics and opportunity costs. But Italy in all its splendor exhorts the tourist to absorb a vast amount of history, culture, art and discovery in a short amount of time. This will set up any lovebird couple for failure, especially if the get-to-know-you honeymoon phase long passed.

I don’t want you to fail in Italy. I want you to enjoy your investment and leave the country with the relationship you had entering it. Having succeeded on that front, I will pass on 10 tips to make your path easier.

1. Fun Zone
There are roughly two types of vacationers: those who read the placards at museums and those who do not. I read them. My fiancée does not. This was the root of why we sat in front of a 4,000-year-old monument in the plaza that second day, with her crying and me staring aloofly at the street while hoping no one noticed.

Figure this stuff out ahead of time. Align on objectives. Do you want this vacation to be about fun and relaxation or seizing the moment? To me, fun is irrelevant when visiting Italy. I could have found plenty of entertaining things to do in L.A. and kept the change on the 6-grand tab. To me, what is relevant when visiting Italy is the fact that you are in mother-effing Italy. You are behind the walls of the Vatican. You are inside the Colosseum. You are underneath David’s manhood.

Truth be told, it’s all kind of boring. I certainly will not see this stuff a second time before checking out a long list of other places first. So let me read the stupid placard while I’m here this one time in my life. Let me see every wing of the museum, even if all the paintings look the same. Let me keep climbing hills and exploring even if we’re hot and tired. We had 10 days in Italy. Go hard or stay at home.

Listen, vacation is a subjective thing and neither side is right here. But I am definitely more right. As the saying goes, when in Rome… it is a more efficient use of resources to fill your time with things you can only do in Rome. I didn’t come here to sit in a café to soak up the “Italian” experience. Sharkeez has an outdoor patio too, and they don’t even care sometimes if you take your shirt off.

2. Pooping Terms
This conversation occurred while we were standing on a step overlooking the majestic Basilica:

Me: (kiss her) How many times a day do I kiss you?

Her: Twenty. (brief pause) I haven’t pooped in a while.

Me: (turn away disgusted; she doesn’t notice)

Her: So after this, pizza and gelato?

If you and your soul mate aren’t on pooping terms yet, talk it over on the plane and reach a comfort level before you land. Because once you’re there, game on. European hotel rooms are tiny. You can run the shower and turn up the television all you want, but the truth will be self-evident.

With nowhere to hide, transparency is the best approach. Communicate and plan ahead. After my fiancée took a shower, I figured it was a good time to go. Now, I don’t know if it was the shower steam or the foreign all-carb diet, but I almost fainted in there. I absolutely destroyed the premises. Seconds after I exited the bathroom, she waltzed back in there to do her makeup and nearly died of shock.

Can you imagine my embarrassment? I repeatedly asked her throughout the next hour if she still loved me. All I know is that if she had done that to the bathroom, I would have taken the next flight back to LAX and we would figure out our relationship when she got back.

Again, try to plan ahead. Because of adjusting body clocks and demanding itineraries though, that won’t always be possible. We had to catch a bus to Cinque Terre early in the morning, and my fiancée didn’t get a chance to use the bathroom before the 13-hour tour. The bowel pressure mercilessly converged on her 90 minutes before the first rest stop, and she could not disguise the pain. I was about to get on the intercom to announce a Level 5 alert like Keanu Reeves in Speed.

There is no getting around it. You have to be on pooping terms with your mate, no matter how romantic you want the trip to be. I have one more word of advice on this, and then we can move on to more palatable topics. European toilets do not keep much standing water. Pretty much only the opening is covered in water before flushing. Unless you are comfortable with leaving NASCAR-quality skid marks, sit back and aim accordingly. Even followup flushes won’t remove the evidence if you hit the wall.

3. Phone
Bring an outlet adapter (thanks BC). Put your phone in airplane mode to avoid charges, and then turn on Wi-Fi. It will not be difficult to find a connection, which of course enables email, social media, and iPhone users to text anyone with an iPhone. Most important, you can pull up Google Maps walking directions. This is especially useful because even when you start walking and lose the Internet connection, you can still see your dot moving on the map and figure it out. If you want to look up a new place, there always seems to be a Burger King or hotel around the corner with free Wi-Fi.

Keep this in mind for Venice, a pedestrian city built on a labyrinth of small islands and canals. Streets might have multiple names or unmarked, arms-length entrances covered by awnings. You can be walking along a row of cafés bustling with Bellinis and cannolis, pivot onto a side street, and wind up at a dead end that makes you want to preemptively reach for the rape whistle.

I don’t care if you are MacGyver in his prime — you will get lost in Venice. If you’re Asian, you might never make it out. I bet there are entire Japanese tour groups who just gave up and are currently sending smoke signals from hostels.

Know your partner. Some people do not enjoy being disoriented or wandering. Let technology save you an argument or two.

4. Food
I do not recommend pegging much of your anticipation and excitement on the vaunted Italian cuisine. It’s good, but no better than that. The mystique comes from Americans with a hard-on for the history and ambience of Italy rather than their taste buds. A New Yorker who studied abroad and lived in Rome recommended Alice Pizza as a hole-in-the-wall with the “BEST PIZZA EVER.” It was fine, but basically DiGiorno with some fun toppings. Ian’s in Madison, Wis., probably throws away slices 10 times better. Italian pizza isn’t even in the same stratosphere as New York, Chicago, San Francisco and many inventive places in between.

The same goes for pasta. Gelato schmelato. I tried many of those pretty sandwiches in cozy shops, and all were eclipsed by the Trader Joe’s sample I had after returning home. And am I really supposed to go crazy over hard, dry bread because I can dip it in oil? Have you ever tried a Red Lobster biscuit?

You might think I am being a provincial biased American, but I think you’re biased by the Italian aura and reputation. Again, there is no right answer, but I am closer to it. America is the fattest, richest, pickiest, most creative country on Earth. We know something about food. We are a melting pot of cultures, and our collective ladle benefits from these varied inputs.

Think of it like having a diverse gene pool. You mix it up and get Derek Jeter. You stay too close to home, and you get Down syndrome.

At the very least, we don’t charge people $5 for water every meal. I am not asking for you to fly in a pitcher from a mountain spring in the Amazon. Just run the tap and put some ice in it. No self-respecting First World nation should make people pay for water. This isn’t Sudan.

5. Tipping
The water expenses are more than offset by dramatically less tipping. You can’t even sign for tip when paying with a credit card. A couple times I had no cash and didn’t leave anything at all. My research and observations indicate that this is OK in Europe. Service charges are built into the pricing and wages, at least enough that the staff doesn’t make its living off gratuities. I remember getting my tip returned in Berlin once because the waitress said it was too much.

That said, I still feel you should tip a little bit, certainly not 20%, as a nominal token of appreciation. I started hoarding 5-euro bills for this purpose, and really even less than that would have been fine for a simple two-person meal.

For tours, I asked our Cinque Terre guy straight up what the norm was, and he said all the tour guides (many of whom are freelance) can’t stand Rick Steves because he promotes the idea that tips are unwarranted. It was a fair point, given that our guides really made an effort to enrich our limited time on vacation.

I ended up tipping him about 10% but noticed that no one else in our majority-American group did at all. It’s a judgment call and personal preference. In hindsight, I like my unofficial 5-10 rule: 5 euros for meals, 10% for specialized services, a couple euros for bellhops and drivers. Try to coordinate with your significant other, break large bills when possible, and limit ATM withdrawals because you will get dinged each time with the transaction fee.

6. Vatican
The kerosene on our fight at St. Peter’s was that we couldn’t figure out the “shortcut” from the Sistine Chapel to the Basilica. The guy at the information desk told us to exit the Vatican museum, so we did and walked all the way around the perimeter only to find a mile-long line wrapping around the plaza. After standing in it for a bit, one of us became impatient and suggested we try to go back through the museum. That’s another thing — know how well your partner handles waiting in line and pack snacks for him/her (let’s be honest, her). Hurry-up-and-wait is an unavoidable part of tourism, but planning can make a tremendous difference. Buy tickets online to all major sights, which lets you skip the big lines. You can’t buy tickets in advance for the Basilica, but there is definitely a way to get there from the museum.

Anyway, we again walked the length of the Vatican walls to the museum, and the armed guards wouldn’t let us back in based on the time stamp of our tickets. At this point, one of us wanted to wait in a long line for food, and the other wanted to wait in the Basilica line. One of us did not feel comfortable splitting up, and one of us did not feel comfortable being inefficient. We eventually made it through both lines and got to the Basilica after baking in the sun, only to find that the dome had closed for the day. Needless to say, there was some spirited sexual intercourse that night.

7. Pompeii
The city wiped out by a volcano eruption two millennia ago is not worth seeing today if strapped for time. But if your fiancée is a teacher who has always been fascinated by the story, then I suppose it’s worth it. Just know that you will not run out of ruins to see in Rome, and Pompeii is not a trivial day trip. The train tickets were expensive and included transfers at stations that made the Howard L stop look like a kiosk at Disneyland.

8. Trains
Riding the trains through Italy is not so bad as long as you maintain an expectation of Murphy’s law. If you are early, the train will be late. If you are literally running to not be late, your assigned car will be on the other side of the platform and the entrance blocked by a family with no apparent purpose in life.

Listen carefully on this one. If you are approaching a station where you need to change trains, get your fat American body out of the seat, grab your stuff, and wait by the exit. We were in the process of doing so at Bologna Centrale when some little girl stepped into the aisle, blocking the way while staring into space like the freak children in The Shining. It took a good 45 seconds to clear our luggage and get her to pass, and it turned out she didn’t even need to stand up in the first place.

By that time, a torrent of people waiting at the station had already rushed onto our car and filled the aisle while loading their belongings. At that point, I should have switched to Karl Malone mode and thrown enough elbows to get to the door. But Americans not from big cities generally aren’t accustomed to that mentality, and we idiotically cleared our stuff from the aisle to accommodate some folks who just couldn’t wait to stow their luggage. By the time I pushed my way to the door, pressing the button didn’t open it.

I thought an Italian lady was calling out to the conductor to help us out, and there was about a minute of tranquility after a stressful situation. Then my fiancée asked, hilariously in retrospect, “Are we moving?” as the train sped off for Verona with us standing in disbelief. I have heard of people missing trains, but not being forced to ride trains that they wanted to exit and then later charged 46 euros for it. I should have refused to pay because no one likely would have pursued any recourse. But then again, I had already burst into the off-limits cockpit and pissed off the conductor to the point where he was yelling at me and making phone calls. So maybe I could have gotten in more than 46 euros worth of trouble by starting an argument with the attendant.

Don’t put yourself in that quandary to begin with. Of course the rest of the trip, we were waiting by the exit doors at all of our train stops. And of course, Bologna Centrale was the only time that we really needed to be ready because we happened to be in the one car with only one exit, during a short stopover at a crowded station, with the child from The Shining.

9. Fight Plan
The swindlers are aggressive in Rome. They might say you’re walking the wrong way just to get you to stop. They might try to impose a “service” on you and then demand money for it. In what has to be a violation of some ethics code, hustlers at the train station dressed in business casual will ask “Informacion?” as if they were staff.

While sitting on a train waiting for departure, we saw a young guy lead a British girl to her seat and put her bag in the overhead compartment. He then asked for money. She was obviously flustered, saying she thought he was staff. She gave him a euro or two, and he said it wasn’t enough. She said that was all the money she had, and again, she thought he was staff. He persisted, basically trying to intimidate this 20-something girl traveling alone.

I made eye contact with her and gestured not to pay him, which caught his attention. He showed me the coins and said this was no good, and I repeated that she thought he was staff. We went back and forth briefly. This punk knew exactly what he was doing. He put his index finger to his lips, not in a “shh keep a secret” way, but more like “shut up or else.” I was too slow to think of a witty response and just repeated what I had been saying, and he eventually walked off.

A substantial chunk of my ego wishes I had punched him in the throat. My fiancée was glad I spoke up but also paranoid that he would be waiting at the train station with his friends ready to throw acid on us. She instructed me not to be stupid if we were to run into this jerk again, who by the way looked like he would get carded at every bar in America.

In Rome specifically, I think it’s pretty easy to find a fight if you react aggressively. I have heard stories of girls being groped but didn’t see anything like that. My fiancée later told me she felt uncomfortable on one of the ghetto trains because a creepy guy was ogling her. I’m fine with that and honestly do the same thing when wearing sunglasses.

Develop a good understanding of how your partner wants you to respond in situations that call for some level of sticking up for yourselves or others. Some girls might want the alpha-male knight in shining armor, and you don’t want them to feel like you wussed out. Some might want you to just walk away, and you don’t want them to feel like you were a hothead who made it worse.

On a less intense level, get on the same page with responses to any overture. As a suburbanite at heart with the tendency to give people the benefit of the doubt, if someone asks me a question, I answer it. A woman at the train station asked me where I was going. I told her. She read the board and pointed me to the platform. She followed me and asked for money. I gave her a euro. She said it wasn’t enough. I shrugged and walked off, feeling stupid.

My fiancée was much more intelligent handling these situations. While I was buying a beer from a sketchy guy on the street, another offered a rose for “free” and tried to put it in her purse when she declined. The way she very loudly announced to everyone in the vicinity that she didn’t want the rose and backed away like a corner trying to cover Dez Bryant made me so proud.

A sweet-natured lesbian on our tour wasn’t so lucky and had her money, credit cards and phone stolen while an accomplice distracted her by shoving some sort of poster board in her face. The point of these anecdotes is not to paint Rome as some kind of lawless danger zone. It is, however, known for skilled pickpockets who exploit carelessness. Comforting a girl who lost all of her vacation pictures would be draining enough without fighting over whose fault it was. Decide ahead of time how much you are willing to engage strangers, if at all.

When you need a break from being so vigilant all the time, ask a Canadian to take a picture for you and prepare to hear his family’s life story. Also particularly endearing when feeling like you can’t trust anybody is seeing the dad in the giant Asian tour group wearing his backpack over his chest so he can safely immerse himself in the camcorder. We have focused way too much on the Zapruder film. Somewhere in a Japanese family’s video albums lies conclusive footage of the second gunman.

10. Olives
My fiancée bought olives, salami and cheese for her dad. The liquid in olive jars makes sneaking one through airport security a 50-50 proposition. We got caught in Pisa, but they did give us the option of pouring out the liquid and going through the security line again. We didn’t have time. Check a bag, pour out the liquid in advance, or buy a smaller jar.

When you land back in the States, don’t declare anything at customs. I naively noted we brought back meat, and the automated passport check put an “X” on our sheet. This forced us to wait in the much longer line. Saving an hour-and-a-half at LAX on a Wednesday night before work after 24 hours of travel is worth the lapse in honesty. Plus the customs agent said he was being lenient in letting us bring back salami.

Just lie. Sometimes it makes things so much easier with no ill effects.


The marriage is still on after 10 exhausting days together in Italy. In the heat of one of our disagreements, I opined that perhaps we should stick with resort-style getaways and then take more sightseeing-heavy vacations with our respective friends and siblings. She was hurt by this suggestion, while I maintained it was a good solution.

I take it back now. In Florence, we bought three purses in two trips to a small leather shop called Moretti Walter. The grandfatherly owner looked like a portly Einstein and was so sincere, ignoring other potential customers while giving us a history lesson of the city and family business. All in beautiful Italian. He would occasionally use a calculator to translate numbers and dates and just kept talking as if a few digits made us understand what the heck he was saying.

At the end, we took a picture together, shook hands, and he was able to eke out in English, “Have a beautiful life.” Maybe the old man says that all the time, but I thought it was a poignant goodbye. Our paths crossed and we shared a moment, and we will never see each other again. It’s kind of sad if you’re in a thoughtful mood, and makes you appreciate what you have. I got to take the best part of my vacation home with me, which was the person I took it with.



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