Jerusalem:
On our first full day in Jerusalem, we headed straight to the Jaffa Gate to hook up with a walking tour of the Old City. Once we wrapped that up, we spent the afternoon down the main drags of Yafo Street and Ben Yehuda, making our way toward our Airbnb near the Mahane Yehuda Market.
Because we hit town right during the national Jewish holiday of Sukkot, the Immas and Abbas (moms and dads) were out in full force with armies of kids in tow. The streets were absolutely packed with people dressed in their formal holiday best—eating, shopping, dancing in the square, and just hanging out. The entire city was absolutely buzzing with holiday spirit.
I’ll admit, I inadvertently booked our trip to Israel right during Yom Kippur and Sukkot. It easily could have been a logistical nightmare, but it turned out to be an awesome mistake. It gave us a front-row seat to experience the high holidays in a way you’d never see back home.
The Western Wall
The absolute centerpiece of the Old City is the Western Wall. The last time I stood in front of these ancient stones was for my Bar Mitzvah back in 1977. I distinctly remember squeezing a handwritten note into the cracks of the wall back then, asking the Almighty for a moped. Hey, don’t judge—mopeds were the coolest things on two wheels in ’77.
Naturally, that wish never came true, so on this visit, I went looking for the note just to see what the hold-up was. No luck. But standing there as an adult with a completely different perspective on life, I took the opportunity to slide a new note into the wall with a slightly more meaningful request.
[The Wailing Wall Protocol]
1977 Request ──> A brand-new motorized moped (Status: Denied)
2026 Request ──> Health, perspective, and continued global travels (Status: Pending)The timing of our trip also allowed us to visit the Wall for the Friday evening Shabbat services, and let me tell you, it was truly spectacular. If you ever find yourself in Jerusalem, make it a priority to see the Wall on a Friday night. T he atmosphere is completely electric—it’s an absolute sight to behold.
Kidnapped by Kindness: Brain Meltdown in a Sukkah
One of the things I love most about flashpacking is the wacky, far-out encounters you stumble into on a daily basis. We had just dropped our bags when Barbie and I set off for a casual stroll through the narrow, twisting alleyways of the Nachlaot neighborhood, which sits right next to the massive, colorful chaos of the Mahane Yehuda Market.
Barbie actually wanted to dive straight into the market action, but I convinced her to skip the crowds for a minute and wander the local residential side streets instead, promising her that’s where the real neighborhood treasures were hiding. Well, I definitely wasn’t prepared for the specific treasure we were about to uncover.
As we were walking, a pretty Israeli woman in her late 30s standing outside with her baby caught my eye. Instead of a casual nod, she warmly invited us right into her courtyard for a Sukkot blessing and a traditional “shake of the lulav” inside their homemade Sukkah (a temporary holiday hut). Her husband, an Orthodox guy, stepped up and led a formal holiday blessing for us using a citron (a massive local citrus fruit) and a bundle of palm and willow branches. Barbie and I both did the official ritual shake, and once the prayers were wrapped up, they sat us down inside the hut, poured us drinks, and handed us homemade holiday pastries that, to be totally honest, tasted a little bit like cardboard.
Then came the conversation. They started diving into heavy religious and spiritual concepts that went straight over Big Doug’s head. I sat there listening intently, all while feeling like my skull was about to physically explode from information overload.
Barbette, on the other hand, was absolutely in her element. She was totally engaged, soaking up this in-depth Orthodox philosophical lecture on the enlightenment of the human soul and body. It was incredibly deep stuff, and despite my best efforts, my internal circuits completely fried. I just sat there in a state of pure bewilderment.
Thankfully, I had my smiling, attentive, and highly personable co-pilot Barbie with me to carry the social heavy lifting and bail me out. Thank you, Barbie—I owe you big time for carrying the team during that intellectual workout. Cardboard pastries aside, getting to share an authentic religious holiday tradition inside a local’s home was pretty cool, and it’s a memory that’s permanently etched into the travel bank.
Yad Vashem
The Yad Vashem Museum, Israel’s official memorial to the victims of the Holocaust, sits on the slopes of Mount Herzl, and it is an absolute, non-negotiable must-see. I had visited the original museum about 25 years ago, and I was incredibly impressed to see that the entire complex and the exhibit presentations inside have been completely rebuilt from the ground up. They did an absolutely phenomenal job with the redesign.
It’s a cryin’ shame they didn’t do as good of a job with the remodel of the Anne Frank House in Amsterdam—which I also visited 25 years ago and felt completely ruined the raw intimacy of the original space.
At Yad Vashem, the historical timeline of the Holocaust is presented in a way that is incredibly captivating, even for a simpleton like myself. We smartly paid the extra shekels for the audio tour, which was so deeply engaging that I lost track of time. When I checked my watch after two hours and realized we weren’t even a third of the way through the exhibits, I knew we had to drastically pick up the pace. Otherwise, we would have been stuck inside for well over eight hours. And let’s be honest: going eight hours without downing a hot shawarma is just plain bad for Big Doug’s soul.
Flashpacker Pro-Tip: In my opinion, the absolute optimal way to digest the massive amount of historical weight that Yad Vashem has on tap is to split it into two visits. Go see the first half of the exhibits on day one, head back to your rental to process all that heavy information (and eat a shawarma) that evening, and return fresh the next day to tackle the second half. Best of all? The museum is completely free of charge to enter. As long-term travelers, we’ve grown completely accustomed to getting nickeled-and-dimed at every major global site, so it was a refreshing change of pace to find a world-class institution where nobody was after your shekels.
Navigating the Jerusalem Attitude
Strangely enough, I found the daily pace in Jerusalem to be much faster and more aggressive than the laid-back beach vibe of Tel Aviv. That was the complete opposite of what I was expecting before crossing the country. Maybe it was amplified because we arrived during the chaotic rush of the Sukkot holidays, but being in one of the holiest cities on earth revealed a few odd cultural quirks that left me a little uneasy.
While the folks in Tel Aviv were incredibly friendly and relaxed, the general attitude on the streets of Jerusalem takes some serious adjusting to. To put it bluntly, a lot of the retail workers, restaurant staff, and hotel employees have completely perfected the twin arts of customer apathy and outright rudeness. If you’ve ever eaten at the famous Durgin-Park in Boston’s Faneuil Hall, you know the vibe—except at Durgin-Park, the sassy attitude is a fun part of the theatrical show. In Jerusalem, it’s the real deal across the board.
Along with the sour attitudes, the sheer physical pushiness of the crowds was something I’ve never seen to this degree in any other country we’ve visited. In Jerusalem, personal space simply does not exist. T he reigning street philosophy seems to be: whoever pushes the hardest wins.
The Israelis specialize in warfare, so they know all the psychological mind games required to win a turf battle—but they met their match with me. I weigh in at a solid 200+ pounds, and the second the shoving starts on the light rail trains, in the narrow market stalls, or around a crowded falafel counter, Big Doug simply flexes, locks the joints, and turns his frame into a solid brick wall. It was game over for those hombres; they bounced right off.
Ultimately, the aggressive street posture didn’t rattle me too much because I quickly realized the locals aren’t just rude to tourists—they’re equally rude to each other. I’m still trying to decipher the cultural root of it, because it is a night-and-day contrast to the communal harmony we experienced back down on the coast.
Despite the rough edges, Jerusalem is easily one of the most visually impressive and deeply fascinating cities I have ever laid eyes on. You can easily get lost in its endless maze of stone alleys, and honestly, that’s exactly what you should do. Where else on earth can you witness so many fiercely distinct cultures and competing world religions co-existing inside such a tiny footprint?
You’ll be wandering down a random cobblestone alleyway, and within a single block, you’ll pass Hasidic Jews in full regalia, Muslim merchants, Christian clergymen, Eastern Orthodox priests, and a massive mishmosh of other global pilgrims all crossing paths to get to their respective mosques, churches, synagogues, and local betting shops.
Jerusalem’s Old City is incredibly compact—clocking in at roughly one single square kilometer—but it is absolutely packed to the gills with intensity. Whatever your personal faith or lack thereof, there is an endless amount of history to look at. Sure, the main holy sites are completely choked with tourist crowds, but at the end of the day, we’re tourists too.
The saving grace here is that shuffling shoulder-to-shoulder through these crowds doesn’t feel like navigating a cheap, commercialized theme park. It’s because Jerusalem is raw, alive, and happening. It’s not some dead, boring ruin city; the people surrounding you in those crowds actually want to be there on a spiritual level. You will see people openly crying, people deep in intense meditation, and people chanting prayers at the top of their lungs.
The New City is almost as fascinating as the old historical center, offering a buzzing modern grid of cool old streets packed with lively cafes and bars where the younger locals hang out. Our strategy in Jerusalem was simple: walk out the front door, get completely lost, and love every minute of it.
But Is It Safe?
Since we started this leg, a ton of people back home have reached out to ask if Israel is actually a safe place to visit. Look, nobody can guarantee what might happen tomorrow, next week, or anytime down the road—that applies to any square inch of the planet. But generally speaking? Israel feels incredibly safe.
Barbie and I walked the city streets day and night in both Tel Aviv and Jerusalem, walked down dark, remote residential alleyways, and never once felt even slightly threatened. The military and all branches of security personnel are absolutely everywhere keeping tabs on the environment.
The specialized tactical forces deployed to protect the crowds attending the Friday night Shabbat services at the Wailing Wall were an absolute sight to see. They looked incredibly intimidating, standing guard with assault rifles in hand, with a collective body language that clearly screamed, “Don’t even freaking think about it.” Long story short: Israel is safe, and honestly, I’d argue it’s probably a hell of a lot safer than whatever major city you’re currently sitting in back in the USA.
Thru the Binocs: The Three-Grand Hat Club
The Shtreimel Enigma
I’ve never come into close, daily contact with Hasidic Jews the way I did while navigating the streets of Jerusalem, and trying to figure out the economics of the lifestyle was a total puzzle. According to a few locals I talked to, a large portion of the strictly religious Hasidic men dedicate themselves entirely to Torah study and don’t hold traditional corporate jobs, relying heavily on community and government assistance programs to get by.
Yet, every single one of them is walking around in an elaborate traditional uniform that looks incredibly expensive to source. They wear these pristine, heavy, long shiny black silk coats paired with massive, towering fur hats crafted from mink or fox tails.
Intrigued by the look, I did a little digging through the glass. These custom-made fur hats are called Shtreimels, and they are definitely not cheap off-the-rack items. A genuine, high-quality Shtreimel will easily set you back in the ballpark of $3,000 USD. That is a serious amount of freaking shekels for an item of clothing. To be honest, they look exactly like the kind of wild, pimped-out statement hats a highly paid professional football or basketball player would proudly rock into a stadium tunnel in the dead of winter. It’s an unbelievable look, and seeing hundreds of them moving through the desert heat of Jerusalem is something you have to see to believe.
Big Doug & Barbie Drop Out of Society 