A Guide to Italy for Brooklyn Hipsters

Go for that party in Como, stay for the expresso

This is usually where you’d find the audio recording, but my AC unit is loud and I would surely perish without it in the time it would take to read this to you.

Younger adults with US passports who identify not as Americans but as New Yorkers, Californians or Global Citizens have made Italy their official summer destination for remote-not-working, consuming illicit substances and expanding the boundaries of their unconventional relationships. While Italy has always had a gravitational pull for people who wear large sunglasses and refer to themselves as foodies at other people’s dinner parties, travel to the peninsula that’s shaped like a thigh boot kicking a pigeon has spiked within a certain US demographic as a result of the rise in elective unemployment and the realization that the food in Portugal—improved by vanity restaurants opened by post-work expats who relocated for the vanity passport—is still largely inedible. If you or someone you know uses alternative pronouns or has heard of Burning Man, it is likely that you will one day find yourself in Italy during the Summer months of April to mid-November for an indeterminate amount of time. This guide will ensure the peakness of the peak experience you seek out in the country responsible for pesto, pappardelle, and the Pope.

Preparations

Italy runs on the chips of American credit cards, and as such, the entry requirements are perfunctory. The only visa you need is your Chase Sapphire, and the only reason the border guard will stamp your entirely optional passport is to channel his disdain when you cheerfully mispronounce, “Ciao!” On the off chance you’re considering buying a round trip flight, this is ill-advised. ­It is inevitable that you will arrive and discover via Instagram stories (or Threads!) or an indiscreet comment in a WhatsApp group that a fringe member of your Burning Man camp (who considers you a fringe member of their Burning Man camp) is in Ischia/Capri/Como hosting a party to which you are not invited—but will weasel your way into by claiming to have “Unicorn K”—and due to FOMO and missing your flight because you slept through the alarm that you will be too high to actually set, you will end up changing your return flight so many times that the change fees exceed the average per capita income of North Dakota. 

Packing for Italy is very easy, because you should bring only your flat-brimmed summer weight hat, amulet(s) gifted to you on Playa, and face chain. Everything else should be bought in Italy so that you can tell people back home that you bought that deadstock silk, abstract-flowered, vintage deepest of v-neck Miu Miu in Italy. 

For a certain kind of traveler, Italian fashion is third only to brightly colored rags sourced from the mercado in Tepoztlan and jeans made of selvedge denim the texture of Communist cement tailored by That Guy in the Shibuya district of Tokyo. If the label says Made in Italy, and the price tag gives your parents heart palpitations when they see it deducted from your trust, you can be absolutely certain that there is a one in twelve chance the garment you’re considering was indeed assembled by the adult hands of someone employed by the fourth generation of an actual Italian family in the factory that looks like a 1950s film set pictured in sepia on their .it website with materials produced by people employed by other (closely related) Italian families. However, you will almost certainly end up purchasing garments that are not actually made in the factory sketched on the tiny pamphlet attached to the label bearing a hand-written price. Despite this fashion fraud, any garment that says Made in Italy but is not actually made in Italy will still look great on you before it disintegrates during your first heavy sweat, because the Latvian children who made it out of Chinese fabric have even smaller hands than the Indonesian children who make clothing that does not say Made in Italy.

Language

As a “citizen of the world” who embodies American entitlement (a descendent of the British superiority complex), you are intrinsically international without speaking any foreign languages because of the geographic range of Saved Places on your Raya profile, the variety of countries in which you have reliable drivers and dealers, and the volume of foreign transaction fees that appear on your monthly Amex statement. The only Italian word you know is the pinched-fingers emoji, which you use every time you post a shot of Carbone’s spicy rigatoni. Luckily, most Italians over the age of 45 begrudgingly speak at least five words of English, and Italians under the age of 45 write best-selling romance novels in English, which they then translate themselves into 9 other languages. There is, however, one word that you should learn so that your travel posse will think that you are fluent when you use it during your very spotty call with Laura (pronounced LAO-rah), your Airbnb host, to complain that the key doesn’t open the door to the villa: (It does, you’re just super high.)

Ciao

This word to Italians is what vibe is to you: it is every third word spoken, and it means anything, everything and nothing at all. Depending on the time of day and context, ciao might mean hello, goodbye, and nice try dickface. Only if you were born in a 17^th century villa in the Italian countryside (owned by your family for at least 600 years), make pesto from home-grown basil and pignoli nuts, and own a vintage green/white Vespa with a faded Italia FIGC football sticker above the wheel well will you ever pronounce ciao correctly, but you will sound cooler to your friends if you at least try not to sound like a Will Farrell character. Ciao appears to the naked eye to be a monosyllabic word, but it is actually a little more than three syllables. This is the phonetic spelling and intonation:

Since every single one of you is an accomplished DJ, you will recognize that the first syllable is a C, the second is an B, and the third is a G. Ciao is sung, not spoken. This is why all Italians are opera singers and most opera singers are Italian: one must literally sing every third word.

Other common words for the more ambitious include: allora (AHLL-or-ah), which means let’s go, what’s up, whatever, fuckit, and YOLO, and occhei (UH-kaiEEEE), which, depending on the context, can simply mean ok, or it can be a very chill way of telling someone to go fuck themselves.

Currency

Much to the chagrin of Italians, who still mourn the death of the long defunct Lira­–because being Italian means you must always be mourning something (the loss of a football match or a horse race, the last sip of your first coffee, your 45-year-old son moving out of your house to live with his wife and children, etc.)–Italy’s currency is the Euro. The cost of food, clothing, and Aperol spritzes is reasonable compared to socialist countries such as France and Sweden, isolationist monarchies such as the United Kingdom and Norway, and countries that exist purely to store and launder ill-begotten wealth such as Liechtenstein and Switzerland. 

To add more suspense to every purchase, Italy has a charming tradition of adding tiny, almost imperceptible incremental fees on top of the very perceptible EU VAT. One will overtly or tacitly agree to a certain price and then find that several creative fees have been added to the sum, much like how the cost of a rental car is enhanced by dozens of line items (airport fee, parking fee, moving fee, profit margin fee, creative accounting fee, incremental revenue directly to the private equity company that owns the rental car company fee, etc.). For example, you will be charged a €3 fee per person for sitting at the table on top of the cost of food and drink, which are the only reasons you are sitting at a table in a restaurant. This annoyance fee is called the coperto. Loosely translated into English, coperto means don’t ask me about my business. If you ask your server what this “coperto” is on your check, they will stare right into your eyes, channel their inner Cosimo de Medici, and tell you unapologetically that, “eet’s for seetting at-a tha table.”  

Climate

Because finding silk kimonos, sheer cotton tunics, and matching pastel chiffon tops and bottoms in winter weight is challenging, and getting high on chartered catamarans and retrofitted fishing boats equipped with Funktion One (or a Soundboks if you’re on a budget) speakers isn’t as fun when it’s cold, you will most likely only ever travel to Italy during the summer months. Summertime weather in all but the northern mountain regions of Italy is identical to that of Tulum, so it is helpful to bring your rose quartz amulet from Tulum to cool your heart chakra. The temperature ranges from a breezy 24 degrees just before the sun rises to a not as breezy 40 degrees, which remains consistent from sunrise until about an hour before sunrise. 

Air conditioning has not yet been invented in Italy or anywhere else in Europe, but fans are highly effective at moving warm air from the fan to your body. It is customary in Italy for people to compensate for the absence of air conditioning by eating spectacular volumes of gelato. Gelato is basically ice cream without the obesity stigma, and as such can be eaten multiple times every day. Unlike ice cream, gelato is only eaten in public and while standing in dense clusters right in the middle of streets and sidewalks.

For people who have read Peter Attia’s book or listen to Dr. Huberman’s podcast and have thus sworn off processed sugar, dairy, and joy: an alternative to consuming 4,000 calories of frozen lactose is a dip in one the many swimming pools that are found behind private villas owned by American movie stars, or a brisk swim in the ocean, accessible from the soaring, jagged cliffs that surround the entire country except for that tiny patch of sand in Calabria. For those who follow Wim Hoff or are Wim Hoff and use cold plunges as both a conversation starter in Aspen/Mill Valley as well as a personality type, do not fret. Simply find a Loro Piana boutique and walk inside, and you will feel like you are back home in your VC/PE dad’s $15k medical-grade cold plunge. The air in these boutiques is just a bit colder than a sushi fridge and not quite warm enough to prevent the occasional hypothermic cardiac arrest of staff. While Brunello Cuccinelli keeps their stores cool with the hearts of their customers, Loro Piana has the air in their shops flown in daily from Antarctica, which is why you can feel justified purchasing a t-shirt for €840.  

Food

The food in Italy is even better than the Fettuccini Alfredo invented by Olive Garden for people in Texas, co-opted by Lean Cuisine for people in West Virginia, and bottled by Bertolli for people in Wisconsin. If you are vegetarian, you can consume chicken and fish, as they are not considered meat in Italy. If you are vegan, you can choose from the country’s many different preparations of nightshade vegetables, which your nutritionist forbade you to eat because forbidding nightshades is fashionable. If you ask for a “salad,” you will receive a plate of sliced zucchini, and if you ask for an insalata mista, you will be presented with a bowl of sliced eggplant, zucchini, and mushrooms with slabs of parmesan flanked by exceptionally large bottles of olive oil and balsamic vinegar (made by the restauranteur’s uncle) along with monstrous olivewood salt and pepper grinders, which are multifunctional and utilized by the police for crowd control after football matches.

Italy is of course famous for its pasta, which is served al dente. Al dente loosely translates in American English to half-bat on the East Coast and half-chub on the West Coast. The range of pastas is dizzying, and even the most annoying eater will certainly find a dish that they can post in their Instagram stories. That said, most of you will not have any kind of pasta experience in Italy, because you have not consumed gluten since the Clinton administration. For the three of you who are actually gluten-intolerant, the majority of people with clinical dietary sensitivities find that native Italian wheat products do not arouse the bloating and inflammation caused by American wheat (which is made of soy beans and pork rinds). People whose gluten intolerance is caused only by an intolerance of being tolerable will find that eating wheat products in Italy still makes them feel less special.

Coffee

While most machinery in Italy operates sporadically and with the lethargy of a trust fund kid at Trinity or St Andrews, espresso (no x) machines operate flawlessly all over the country despite the fact that most machines predate WWII and are operated by men who predate WWI. It is known that Italy lacks a space program because the top designers and engineers matriculate to espresso machine companies, with Scuderia Ferrari a distant second choice of employer. ExpressoEspresso machine companies employ 1 in 4 people in Italy and the sale of these machines to Brooklyn and Venice Beach coffee shops are responsible for 23% of the trade between Italy and the US.

Despite the quality of the coffee, Brooklyn-based travelers will be frightened to find that Italy has not yet invented alternative milk. Along with your peptides, adaptogens and nasal k, travelers from Williamsburg and the more expensive parts of Greenpoint and Bushwick, Venice Beach and the US protectorate Portland, Oregon are permitted to bring their own alternative milk to Italy. Any barista will always happily take your special milk and froth it for you with their steam wand, which in Italian is called a cazzo. You will find that coffees in Italy are significantly smaller than their American counterparts. While the average cappuccino in the United States is one pint, Italian cappuccinos are just shy of a thimble. This is not only the reason for their accessible price – between €1 to €2 – but also why one can have twenty to thirty a day without becoming schizophrenic. Note that to order a cappuccino after 11am in Italy you will need to show a valid American ID or a note from your doctor explaining that you suffer from osteopenia due to calcium deficiency.

Wellness

Athletic travelers who don’t consider pasta a sport will find several gyms in the country. Two of them are in converted hotel rooms at Sheraton Four Points in Milan and Rome, and one of them is in the basement of a retired porn star’s home about an hour outside of Turin. Gym attire is somewhat more conservative in Italy. Women typically wear clothing, and men wear jeans and either a silk polo shirt or a linen button down with a braided belt and loafers without socks. (A reminder that cold plunges can conveniently be found in any Loro Piana boutique and the entire country is an infrared sauna from early April until mid-November.)

Traveling within Italy

There are countless delightful places in Italy to which you will be drawn. These places include Milan (for 7 hours of pre-travel shopping), Florence (to post a photo of David with a wistful, virtue-signaling remark about Michaelangelo’s repressed sexuality), Forte dei Marmi, Capri, Como, Puglia (POO-lee-ah), Stintino on Sardinia, Cefalu on Sicily, and, for those with staggering financial abundance who settle for nothing but the finest Fettuccine Alfredo, Il Pelicano. As such, it is essential to understand the nuances of mobility in Italy. Fundamental to this is the time conversion, which has nothing to do with the 6-hour / 11-hour time difference: in Italy, one US minute is equal to approximately 1 minute and 93 seconds. For example, when an Italian tells you that your table will be ready in 10 minutes, this means the table will be ready in just under 30 minutes. When you tell an Italian to meet you for a 7pm dinner, they will make a mental note that you must have a serious health problem, and will arrive for your 7pm dinner—entirely free of contrition—promptly at 8:25pm.

The only entities in Italy that operate on a universal timetable are the trains, which – unless canceled for no apparent reason – are never late. You will miss every train you book in Italy. This is because Uber has not yet been invented in Italy. AppTaxi, the Italian taxi-hailing app does not work because the drivers of the 5 taxis in the country carry Nokia flip phones. If you try to walk from your hotel to the train station, which in literally every Italian city is never more than 12 minutes on foot from your Airbnb, you will most likely suffer from heat stroke. On the off chance you make your train, you will be seated next to an older Italian businessman who works (works!) in middle management for a trucking company, refuses to speak any of the 5 words of English he knows, and knows that American millennials are the reason the world is terrible.

 Given the complexities of train travel, you will be tempted to rent a car. As a result of inflation and you, daily car rental rates hover between €400 and €900 for a micro-sub-compact vehicle, which is suitable for a polycule of five with five RIMOWA or Tumi rollers, three garment bags, and two designer hat cases. When you forget your dry cleaning bags and vapes at the AirBnB, Laura will gladly ship them to whomever buys them on eBay. Drivers drive on the right side of the street unless they are in a disagreement with another driver. Be advised that in order to give police sufficient time to drink espresso all day at gas stations, invisible speed cameras are placed every twelve feet on every road in the country. If you slip over the speed limit for more than six American seconds, your parents in Connecticut will receive a fine of €3,000 long before they receive your postcard.

Italian Romance

There is really only one rule in Italy when it comes to romantic pursuits. If you are a male, do not make the mistake of hitting on a woman who is with a guy. The more attractive the woman is, the more likely you will be followed to the bathroom by her male partner and not come out. The more attractive the guy is, the more likely you will be followed to the bathroom and asked in tears why you didn’t hit on him.  

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You may be tempted to follow your DJ friends (who are following your credit card) from one summer music festival to the next and leave Italy to the Fettuccine Alfredo crowd, but this is kind of like buying IKEA instead of an antique. You know what you’re going to get with an IKEA product—it takes a lot of sweaty effort to put it together, it doesn’t look nearly as good IRL as it does online, and you end up with buyer’s remorse and a weird rash. Sure, an antique isn’t practical, and it doesn’t really work, but it’s pretty and it has a story that people will at least pretend to want to hear. This kind of sums up Italy today: beautifully designed, and nothing really works (except for the espresso machines), but people would rather hear about your multiple gelato orgasms than Solomun’s set at Destino Ibiza, because they saw him at Pacha last week.