Issue #14 · Follow Me to Weird Places

“Follow me to weird places, Emily.”

That’s what my friend Sharon whispered to me one night, as we were sipping our fourth or fifth Aperol Spritz at a funky dive bar in Naples, Italy — a city that was originally never on my travel bucket list. We had taken the train up from picturesque Sorrento earlier that morning in order to do a food tour, as we had grown sick of the Amalfi Coast’s romantic honeymoon vibes and pizza a portafoglio was a calling.

Fast forward twelve hours and we had intentionally missed the last train back home until morning, as we were having way too much fun on this spontaneous day-trip turned all-nighter. Prior to this, I had only ever heard those frequently repeated negative stereotypes that paint Naples as a hectic, dangerous and seedy city, so I mentioned being pleasantly surprised by how much I was enjoying myself.

Naples is what I would consider weird by Italian standards — weird, simply meaning a bit off the beaten path. Compared to Venice or Rome, it’s usually lower on most tourists’ bucket lists (aside from maybe some Nassau County folk who want to get in touch with their Nonna Lucia's roots, of course). And I’m not talking about the sun-kissed shores of Positano — when I say Naples, I mean the city city. It’s fair to assume that the rolling hills of Tuscany or a grandiose villa in Lake Como appear with a bit more frequency in your average Italian vacation daydream.

That being said, I spent seven wonderful weeks exploring Italy that summer, and this unplanned night still stands out as one of the most memorable, lack of toothbrushes aside. That’s because Sharon was only half-joking when she uttered that now legendary quote that’s been forever etched into the lexicon of my travel friend group — she had a few years head start on me with full-time travel and had already figured out that weird places are usually much more fun to explore.

I've since followed her advice (and often her, herself) to even weirder places than Naples: Tbilisi, Georgia; San Juan del Sur, Nicaragua; a self-proclaimed independent republic in North Macedonia called Vevčani — just to name a few. If you spend a day exploring with Sharon, there’s a good chance you’ll end up in an abandoned underground bunker, a speakeasy not listed on Google Maps, or a random music festival without knowing a single performer. Pinky promise you’ll have a good time, though.

I’m thankful for friendships like hers which initially pushed me out of my comfort zone — and also for the 90-day Schengen Zone limit which has required me to venture further into eastern Europe and northern Africa in order to extend my “European Summers” (classic) by an extra month or two — see you soon, Belgrade! To be fair, compared to the rest of my circle of travel friends, I still haven’t even strayed that far off the typical nomad trail yet, though my hesitant father would probably disagree — hey Dad, I’m going to Cambodia and Laos in 2024, consider this your warning.

By going off the beaten tourist path, sometimes you hit the jackpot and stumble upon a hidden gem a few years before it reaches the mainstream radar. Ljubljana, Slovenia and the Albanian Riviera both come to mind, although that’s changing quickly — go now while there’s still time! Other times, you just have to chalk things up to a “cultural experience” (my favorite way to describe adventures that don’t go quite according to plan). But hey, at least you’ll have a funny story to tell.

One thing that never gets old: The baffled looks I get when I tell someone back home that I’m heading to Serbia or Cyprus — or better yet Georgia (“yes, it’s also a country”) or Bosnia & Herzegovina (“nope, it’s just one country”). In fact, my biggest takeaway from three years on the road is that people (ahem, Americans) asking "why the heck are you traveling to [location X]?!" has become an excellent benchmark of how much I'll probably love [location X].

Now, I completely understand if Barcelona or Paris or Rome are still on your European summer vacation itinerary. Major bucket list cities like those are sort of a rite of passage and it’s hard not to have a good time* even amongst July crowds or August heat. Just proceed with caution — the Italy section of Epcot was designed to mirror the stunningly beautiful Piazza San Marco in Venice, but between social media and overtourism, sometimes the real Piazza San Marco feels more like Epcot.

So my only suggestion for your next trip is that you also visit a few weird places — wander outside the main tourist zones, embrace the quirks of secondary and tertiary cities, choose a restaurant based on its vibe over its rating, hop on the train to a place you pick off the departures board, or at the very least, leave some room in your itinerary for spontaneity. After all, you want to have an Eat, Pray, Love life-changing cultural immersion moment of your own? Let’s not forget that Liz Gilbert’s first major breakthrough came when she went on an impromptu trip to — of all places, Naples.

* * *

*As long as you don’t lock yourself out of your apartment in Rome at 3am. That was not a good time.

Related: This TikTok made me die inside and I need to share my pain with the rest of you (even if it’s a parody, some of the comments aren’t).

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Here’s a list of every issue if you want to keep reading!

• Issue #16: Embracing the Blank Canvas [Sep 2023]

• Issue #15: In Pursuit of an Endless Summer [Aug 2023]

• Issue #14: Follow Me to Weird Places [Jul 2023]

• Issue #13: Self-Inflicted Social Overload [Jul 2023]

• Issue #12: Schlepping It 🎒 [Jun 2023]

• Issue #11: Finding My “Next Thing” [Jun 2023]

• Issue #10: Book the Damn Flight and Just Go [May 2023]

• Issue #9: Choosing Your Own Life Adventure [May 2023]

• Issue #8: Eat, Sleep, Write, Repeat [May 2023]

• Issue #7: My First Month of Indie Making: An Honest Review [Feb 2023]

• Issue #6: Ten Years of Making Money on the Internet [Jan 2023]

• Issue #5: The Modern-Day Mission Trip [Dec 2022]

• Issue #4: Ready, FIRE!, Aim [Nov 2022]

• Issue #3: A New City Every Month: An Experiment in Change [Aug 2022]

• Issue #2: Defining My North Star as a Nomad [Dec 2021]

• Issue #1: One Year on the Road: Looking Back [Oct 2021]