Tel Aviv had been a destination on my radar for quite some time, so it was a must-do when planning my year of travel in 2019. I had never been to Israel (or anywhere in the Middle East), but I had a lot of Jewish friends who had taken birthright trips, so I was always hearing about their visits to the country and feeling a bit left out. I planned six nights in Israel (split evenly between Tel Aviv and Jerusalem), followed by five nights in Jordan (Wadi Rum, Petra and Amman) and two nights in Beirut, Lebanon.

Pro tip: Do not plan an itinerary that includes both Israel and Lebanon in the same trip! It was extremely naïve of me to do so, and while it ended up being fine, I would not recommend that anyone take on the extra stress of visiting these two countries that are sworn mortal enemies in any near-subsequent fashion. I’ll cover this in detail in my Beirut post, so read that if you care to learn more.

I’ll admit that I was a bit anxious about traveling in the Middle East for the first time on my own. Enter David. My good friend and ex-coworker/ex-boss, David had told me that Petra was one of his dream travel destinations, and if anyone needed a vacation, this guy did. I was also anxious about traveling with him, but I decided to invite him along. I just laid out some ground rules:

1) Separate hotel rooms, and 2) We were not going to be hanging out together 24/7.

He accepted my conditions, and we agreed to meet at TLV in mid-September. We’d be avoiding the Jewish high holidays in October, and I hoped that the weather would be starting to cool down a bit by then.

Getting to Tel Aviv

While David and I were both flying from New York, he (in typical David fashion) waited forever to book his flight, and then decided that he couldn’t justify the price for a business class ticket on the nonstop JFK>TLV Delta flight that I had booked. He ended up flying Royal Jordanian with a short connection in Amman. Meanwhile, I had paid for a coach ticket months in advance, then upgraded with one of my global upgrade certificates, so I got to enjoy the nonstop flight in style (and at a great deal).

The view of Tel Aviv as the plane began its descent

While our flights were supposed to land at the same time, I arrived early, so I waited for David at Ben Gurion Arrivals and we shared a taxi to Jaffa together.

Staying at The Jaffa

I should also note that David and I weren’t even staying at the same hotel. I had booked The Jaffa with Marriott points, but by the time David got around to booking, rooms weren’t available with points, and he didn’t want to pay $600+/night for the hotel. He did his best to keep things easy by finding a less expensive hotel in the area.

I received a warm welcome at The Jaffa, which was much appreciated after the long flight
My room at The Jaffa. The historic complex used to house the French Hospital, hence the oddly-placed window.
My mirror was also a TV
This walkway was cute, but ultimately led to nowhere
The Chapel bar/club attached to The Jaffa

First Night Out in Tel Aviv

Although David and I were both struggling from serious jet lag (Tel Aviv is seven hours ahead of New York, and we landed at 5:10pm), we were determined to power through the night. We had arrived on Friday evening, which was technically Shabbat, but I knew that many of the kids would head out to the bars and clubs after fulfilling their obligation of dinner with family. After a drink at The Jaffa, we headed to Suramare, a hidden rooftop bar, for drinks and snacks.

The entrance to the bar was hidden in this odd gas station garage
Woohoo, we found it! Anyone who knows David could probably guess that multiple shots were involved.
They eventually moved us to a better seat by the view. And more shots were consumed.
I was still standing at the end of the night and had to pose at this video game photo booth in the odd gas station garage

Day Two in Tel Aviv

Honestly, day two started out pretty pathetically. We didn’t have anything planned until our 5pm walking tour, and we were both wrecked from jet lag and overdoing it on our first night out. If I’ve learned anything in all my travels, it’s to keep it low-key on night one (if not nights two and three as well). If you want to have any chance of adjusting to a massive time difference, do not mess it up by staying out until the wee hours of the morning when you first arrive. Unfortunately, I was dealing with a master manipulator, and all my wisdom went out the window with the first shot.

We finally motivated to meet for a late lunch at a restaurant by my hotel. These were just the side dishes. OMG, I was in heaven.

Our walking tour was a bit of a bust. It was nice to walk through some different neighborhoods, but the guide was totally dry and I was having a hard time staying engaged with the content, as much as I wanted to learn. David and I both agreed to peace out at the halftime break, which also gave us time to get ready for dinner.

Can you tell how I felt about the tour?

Dinner was at Mashya, which I did not document at all, but I remember it being pretty good.

Then we had drinks at Imperial, where I’d suggest booking in advance. We planned to go before dinner, but couldn’t get in, so we put in our name for a bar spot after dinner. The cocktails were excellent.

Cocktail menu at Imperial

We started chatting to the American tech bro sitting next to us at the bar, and things got oddly friendly. After a few drinks, we bade him farewell, but we were never able to determine who he was trying to hit on. Both of us? Was he just extremely friendly? Something was off, but we couldn’t figure it out.

We were baffled

Day Three in Tel Aviv

Our last full day in the city was Sunday, which one would think would have a fun end-of-the-weekend vibe if one was ignorant like I was. Alas, Sunday in Israel is actually like Monday in most of the rest of the world. I had booked us a brunch reservation at Claro, which turned out to have more of a business lunch scene on Sunday. Except we were on vacation and wanted a party brunch! Fail on my part.

After our disappointing Sunday brunch, we decided to walk along the beach back toward Jaffa. David wanted to hang out on the beach, but I wasn’t feeling it. I’m not sure if it was the lackluster brunch, jet lag or our omnipresent hangovers, but the scene was set for our first tiff of the trip.

At least we had a nice view of the Jaffa Lighthouse as we argued

“Why don’t you want to hang out on the beach?” -David
“I just don’t feel like it.” -Me
“C’mon, what is your problem?” -David
“I told you we weren’t going to hang out 24/7 on this trip!” -Me
“Why are you in such a bad mood?” -David
“I just don’t want to hang out on the beach!” -Me
“Are you mad at me?” -David
“Leave me alone!!!” -Me

Some more ridiculousness ensued, eventually resulting in me heading back to The Jaffa to relax and have some much-needed quiet time by the pool. Sometimes being with David felt like being with my brother, if my brother was two years older than I was and had also been my boss for the last ten years. Fun times.

Looking back toward the city and regaining my cool

Somehow, we both rebounded after a few hours of alone time. I was suddenly the happiest I had been on the entire trip when we met up again.

Dinner was at North Abraxas, which was possibly my favorite meal in all of Israel. Check out menu item #2 under Breads. “4 spicy instruments that will swirl the soul”? I was so in.
These were the four spicy instruments. I can’t say that my soul was necessarily stirred, but my taste buds were absolutely enraptured.
Post-dinner drinks were at Par Derriere. I was dying over this girl’s outfit. Cut-off shorts and stilettos?! I’ll give her credit for rocking the look with confidence.
My attempt at pretending to take a selfie while actually capturing whatever was going on in the background
And that’s all, folks!

While we had some rocky moments, David and I came out on the other end of our Tel Aviv trip with our friendship intact. We had gotten the party section of our itinerary out of our systems and it was now time to move on to the cultural section. Jerusalem, we were coming for you, ready our not.

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