The Grand Finale: Where's Waylen Concludes
What should have happened vs What actually happened
Well, after 17 days of the most unexpected journey of my life, I made it back to New York. I landed at about 1:30 am, Ubered home and after a well deserved shower—and some YouTube doom-scrolling—I was in bed and asleep by the crack of dawn.
With all that being said, and being safe and sound back at home, I thought it would be fitting to compare what was supposed to be a peaceful European cultural tour with the international survival adventure that actually unfolded. This is also a great opportunity for all you who couldn’t navigate the perils of Substack to see my other posts, to see them chronologically and to have all the links in one place. Spoiler alert: these two timelines couldn’t be more different.
Day 1
What Should Have Happened: After a smooth flight from New York to London, I would have made my immediate connection to Berlin. Then, I’d check into my beautiful hotel (read hostel) just a 15-minute walk from the Berlin Philharmonic. Perhaps dinner at the Chabad Center, then the concert I’d been waiting months to see—Andrea Vanzo, Gibran Alcocer and Yehezkel Raz. I’d then end the evening with a romantic (and very lonely) stroll along the Spree River before bed.
What Actually Happened: Flight to London went fine, but then disaster struck at the gate for the Berlin connection. Passport expiring within 90 days = no entry to Schengen zone = no Berlin, no concert, and no European adventure. Instead of the Berlin Philharmonic, I spent the day being escorted out of Heathrow by the lovely Lexie, getting rejected by the U.S. embassy, making casual racist small talk with a Sainsbury’s manager, and ultimately fleeing to Cardiff, Wales. At least I managed to visit three countries in 24 hours—just not the original three.
Day 2
What Should Have Happened: Wake up refreshed in Berlin, spend the day exploring the Gemäldegalerie and National Gallery, visit the Holocaust Memorial. Interview a shliach about Ukrainian refugees he’s been helping. A day of culture, history, and meaningful journalism in one of Europe’s great capitals.
What Actually Happened: Woke up in Cardiff, Wales (definitely not Berlin). Explored Cardiff Castle, got asked for a photo by an Asian tourist, met Roy the enthusiastic museum guide with the Palestinian flag pin, saw some Beis Rivkah girls who turned out to not be Jewish, and met the local shliach. Then I took the train back to London for the Yehezkel Raz concert at World Heart Beat, where I sat close enough to see his gray hair and black Converse sneakers. Met Yaron the digital nomad and had a solid schnitzel wrap in Golders Green.
Day 3
What Should Have Happened: Morning flight from Berlin back to London, spend the day exploring the city, then attend the wedding in the evening—a perfect blend of sightseeing and celebration.
What Actually Happened: The London wedding happened as planned! Finally, a convergence point where both timelines matched. Attended the wedding, met Raf who actually knew Japanese literature, farbrenged about Aharon Strashelye and what it means to be a chosid, then made the brilliant decision to hit the casino afterward until 4:15 AM before catching a flight to Israel.
Day 4
What Should Have Happened: Catch my scheduled flight from Luton Airport to Tel Aviv, arrive refreshed and ready for my cousin’s bar mitzvah at the Gush Etzion winery. End the day not exhausted, enjoying drinks and celebrating family milestones in the Holy Land.
What Actually Happened: Casino hangover plus ETA visa system crash equals missing the 7:25 AM flight to Tel Aviv. Spent the morning crouched on Luton Airport floor frantically trying to get Israeli visa approval on broken government websites. Miraculous rebooking to a later Gatwick flight, bus ride through London traffic, and finally making it to Israel on Wizz Air’s medieval torture seats. Arrived exhausted, grabbed disappointing falafel, and collapsed in Jerusalem Airbnb.
Day 5
What Should Have Happened: Drive north to Tzfat to visit my sister, continue to Yokneam to see my friend Netanel, possibly even make it to Caesarea to visit Mendy Mann. A lovely Israeli road trip connecting with family and friends, ending back in Jerusalem.
What Actually Happened: Woken at 3 AM by first-ever rocket alert. Discovered that war had broken out while I was sleeping. Spent the day walking through eerily empty Jerusalem streets, getting unsolicited fitness advice from an elderly man about my “matchstick arms,” visiting completely deserted Machane Yehuda market.
Day 6
What Should Have Happened: The big day—my cousin’s bar mitzvah at the Kosel. Celebrate this milestone moment with family, enjoy a holy Shabbat filled with oif simchas.
What Actually Happened: Bar mitzvah at the Kotel did happen, but I didn’t make it. Shabbat was punctuated by sirens and shelter runs. Friday night found me sleeping on my cousins’ outdoor couch watching rockets streak across the sky like shooting stars. Motzei Shabbat shelter visits with colorful Jerusalem apartment building characters, including the man with the ponytailed dog and the woman scrolling Facebook during rocket alerts.
Day 7
What Should Have Happened: Early morning 7 AM flight from Tel Aviv to Rome. Arrive and head straight to the Borghese Gallery for some Renaissance masterpieces, then evening tickets to see Ludovico Einaudi in concert. Art, music, and Italian culture in perfect harmony.
What Actually Happened: Still stuck in war-zone Jerusalem, coming to terms with the new reality. Multiple daily shelter visits becoming routine, interviewed Rabbi Gluckowsky from Rehovot, discovered Pesek Zman chocolate superiority. Rome felt about as accessible as Mars at this point.
Day 8
What Should Have Happened: Full day exploring Rome—the Colosseum, more galleries, and an interview with the local shliach for a Chabad.org article. Evening flight to Dubrovnik, Croatia, checking into a stunning waterfront Airbnb as the sun sets over the Adriatic.
What Actually Happened: Moving day from obstinate landlord to lovely French/Moroccan Machluf. Spent the evening wandering Mamilla Mall like an architectural tourist, running fingers along carefully numbered stones. Had surprisingly decent Hatch schnitzel (8/10!) and met accomplished South African lawyer/marathon runner Chana in the bomb shelter.
Day 9
What Should Have Happened: Explore Dubrovnik’s old city, visit that famous beach everyone talks about, then take a scenic bus ride to the Bay of Kotor in Montenegro. End the day in one of Europe’s most beautiful settings.
What Actually Happened: War correspondent day! Attempted French diplomacy, hitchhiked to Hebron with Nuchem David the Gerrer, got premium heritage tour from my cousin and may have liberated—read “stolen”—a 3,000-year-old pottery shard.
Day 10
What Should Have Happened: The dream day—open my laptop overlooking the stunning Bay of Kotor, start writing my novel in paradise. The Airbnb had breathtaking views, perfect writing atmosphere, and the kind of peace that makes creativity flow.
What Actually Happened: Failed mission to reach Tel Aviv impact sites due to security cordons. Ping pong humiliation by bar mitzvah boy cousin, writing Chabad.org war journalism, and reflecting on my elte-Zeide, Srulik’s yahrzeit.
Day 11
What Should Have Happened: Lazy morning in Montenegro, drive to Budva to interview the Chabad rabbi (an exclusive story since Chabad.org had never covered Budva before), then drive to Podgorica for an evening flight to Katowice, Poland. Land around 10 PM at a beautiful B&B with rental car ready.
What Actually Happened: Epic Jerusalem wild goose chase day! Three taxi drivers refused to take me to Har Hazeisim, followed by the Great Potato Kugel Quest—visiting multiple establishments searching for something to rival Dovid Malka’s Carroll Street perfection (spoiler: impossible mission). Capped off with a 7,500-step nail clipper hunting expedition that nearly broke my spirit until the tiny makolet next door saved the day.
Day 12
What Should Have Happened: Begin my genealogical pilgrimage—drive from Katowice to Chrzanów to explore my Mandelbaum family roots, then to Pacanów for Jager family history, finally arriving in Krakow for a look around the old city.
What Actually Happened: Family history research was probably the last thing on my mind as I dealt with more pressing questions like “Where am I?” and “How do I get home?”
Day 13
What Should Have Happened: Drive to Leżajsk for Shabbat at the grave of Rebbe Elimelech. Check out the site where my paternal grandmother’s mother was born and the inn that her parents ran in the center market square.
What Actually Happened: Shabbat in war-zone Jerusalem. Friday night meal in the same courtyard where I’d watched rockets streak overhead the week before and ridiculously early 10:30 AM Shabbos meal where I spectacularly failed to eat anything my cousin’s wife cooked.
Day 14
What Should Have Happened: Explore Tarnów (my grandmother’s birthplace) and Tarnogród (her mother’s father’s family origins), plus other small Polish towns. A day of walking where my ancestors walked, seeing the places that shaped my family’s story and trying to find a few kvorim along the way
What Actually Happened: Lazy Sunday novel-writing (rabbi-priest-imam story that will inevitably join my 65 other abandoned novel ideas), family phone calls, first birthday party with escape route planning discussions, tragic forgotten-backwards-Chabad.org-cap incident during Jerusalem walk, and the discovery of genuinely good schnitzel sandwich (8/10).
Day 15
What Should Have Happened: Continue Polish family research in the morning, then a 5:50 PM flight from Krakow to Amsterdam, arriving around 10 PM to check into a beautiful Amsterdam hotel. The beginning of the end of a perfect European tour.
What Actually Happened: 3:30 AM departure in Leizer the Vizhnitzer’s 400,000-shekel Toyota Sienna, stunning sunrise over Dead Sea and Negev desert, Egyptian border crossing comedy, meeting Mahmoud the Bedouin driver who blessed me to find a wife, drive through ghost-town Sinai with abandoned development projects, aggressive Egyptian luggage handlers nicknamed Flotsam and Jetsam, and finally boarding a plane out of the Levant.
Day 16
What Should Have Happened: Brief Amsterdam morning—early wake-up, maybe explore a coffee shop, then 10 AM flight to Houston arriving 1:15 PM. Time to grab lunch, hang out with a friend, and head relaxed to the wedding.
What Actually Happened: 13-hour flight via Saudi Arabia with Tahitian woman living the most bizarre international marriage arrangement ever (husband banned from America, living in Saudi, they visit each other once a year). Eight-hour-assisted sleep, then the grand finale: 46 hours after leaving Jerusalem, finally arrived in... Houston! The epic international escape route had somehow delivered me to the exact same Houston wedding that was always the plan. Arrived mid-chuppah in casual clothes and signature backwards Chabad.org cap, surprised the groom perfectly, met the incredible Pinchas Aloof (sat at Friediker Rebbe’s table, present for Israel’s independence, Korean War veteran, Berlin Wall witness).
Day 17
What Should Have Happened: Triumphantly fly back to New York City and be done with this adventure, receiving plaudits and adulations from my hoards of fans who awaited my return.
What Actually Happened: Interviewed Mr Aloof for hours on end and had a very, very long Uber ride to the Airport with C and her stories about Principal Jeffrey Carter’s self-written obituary.
—
Thank You.
Thank you for joining me on this absolutely unhinged journey where nothing went according to plan, and yet somehow everything worked out in the end.
Thank you for following along as I discovered my passionate love affair with Pesach’mon chocolate, learned that Wizz Air seats are a human rights violation, experienced what it’s like to navigate international borders during wartime, met incredible people like C the philosophical Uber driver and Pinchas Aloof with his century-spanning life story, survived delays that turned into adventures and adventures that turned into survival stories, discovered that sometimes the journey really is more important than the destination (especially when you have no control over either), and witnessed firsthand that the best-laid travel plans are really just suggestions the universe uses for comedic inspiration.
What started as a peaceful European cultural tour became an international odyssey that taught me more about resilience, adaptability, and the kindness of strangers than any planned itinerary ever could have.
Sometimes the trip you don’t plan is exactly the trip you needed to take.
From New York to New York, with love and exhaustion,
Waylen