Chapter 55: Summer in Spain

Ibiza, Mallorca, and Marbella!

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Five years ago, I was lucky enough to spend a weekend on the mythical Mediterranean Island of Ibiza. As a 21-year-old fraternity president who played Levels by Avicii (and its remixes) no less than 500 times at various pregames, darties, and disgustingly unsanitary parties over the previous few years, I needed to see for myself why Mike Posner took that pill.

Unfortunately, I didn’t account for jet lag ruining my initial experience, and I spent the first ~36 hours or so as a sleep-deprived zombie.

Fortunately, I’m now a 26-year-old with a fully-developed frontal lobe (though some have their doubts), and I was prescient enough to spend a few days acclimating to the new time zone by deleting tapas, espressos, and an aperol spritz or 12 in Barcelona before heading to Ibiza.

With a lineup featuring names such as Calvin Harris, Diplo, and Kygo, it was an excellent weekend to run it back on Spain’s finest party island, and I would have the pleasure of being joined by 40 of my closest business school friends, whose names won’t be mentioned should any affiliation with me, at a later date, lead to them unfairly being part of an extended criminal investigation into my past.

Not that I did anything particularly illegal in Ibiza (other than smoking a cigarette in a venue, which may not be 100% legal, but it’s Europe so who cares? It’s still objectively cooler than hitting a vape).

I also don’t feel like leading off a blog post with 40 names of my associates like a genealogical record from the Gospel of Matthew. Ian, my roommate on the trip, will be the lone exception.

The flight to Ibiza from Barcelona was only 30 minutes or so, and on arrival, we headed to the hotel to hopefully check-in (we couldn’t).

I was hit by a nostalgia bomb upon arrival when I realized that this was the exact same hotel I had stayed in 5 years ago. The tattoo parlor in the lobby was a dead giveaway.

Ian, being a meathead in the best possible way, found a kick-ass gym 5 minutes down the road, so we headed there to pass time by pumping iron (shirtless) until we got closer to check-in.

I will never do deadlifts with Ian again. 5x10 straight bar deadlift is actually psychotic.

After getting our room keys, we headed up, showered, and changed for the day. The plan for the night was to rip a Calvin Harris concert at Ushuaia (not to be confused with the southern-most city in Argentina, which we were quite far away from), so I grabbed dinner and then headed back to the hotel to pregame.

Our hotel felt like a mixture between a freshman dorm and summer camp, as ~25 of us were all in the same hall, girls running around comparing outfit choices and guys hopping from room to room with cheap bottles of vodka and tequila.

I headed to the show around 8:30, arriving fashionably late (but still plenty early for the headline act). There was a conveniently located bar to the right of the stage that provided an excellent line of sight to Mr. Harris, and I spent ~$250 at that bar over the course of the show.

Hell hath no fury like evaluating one’s credit card transactions after a weekend in the Panama City Beach of Europe.

Photographic evidence appears to confirm that I did, in fact, shut the concert down, and after failing to hail a cab, I managed to run into my broader group at a Mexican restaurant on the walk home.

Not a terrible way to start the weekend, no?

The following day started similar to the previous: with Ian saying, “Wake up, let’s go to the gym.

My first thought was, “Respectfully, I’d rather bash my head into a wall,” but my next thought was, “You’re drinking too much to not go to the gym and your body is going to degrade like a melting ice cream cone.”

Vanity, not discipline, is the key to making it to the gym every day, in my experience.

After a much less productive pump session than the previous day (I was in and out in approximately 45 minutes), I headed back to the hotel to delete a calorie-rich, flavor-deficient wannabe full English breakfast before crawling back into my cave of a room to hibernate for hours.

I emerged a new man, ready to take on the world once again, and went to the pool to drink a cervecita. Today, we had a booze cruise around the island (like the hotel we were staying in, I had done this exact same cruise 5 years ago. I also went to Ushuaia 5 years ago, but I think I saw Steve Aoki, not Calvin Harris), so I walked over with a group of the guys to check-in.

The “cruise” was a weird setup. The bottom floor had a bar, but it was also filled with regular ferry seats and no music other than what drifted through the ceiling from the DJ above.

Upstairs was more lively, with a past-his-prime DJ desperately attempting to rally the crowd, but 2/3 of the upstairs deck was filled with tables and chairs that had to be reserved, and most of these slots were occupied by interesting characters such as a group of 3 British dudes, adorned in matching green onesies, lighting their parents’ money on fire.

I spent the first half of the boat downstairs, mainly on the outer deck, before my buzz reached a level sufficient for me to engage in the upstairs activities. Someone in our crew bit the bullet and copped a table, and I leaned into the ridiculousness of the whole thing.

After the boat tour, I kicked by the pool with a few of the guys for a bit, realized that I had completely missed the group Uber to dinner at a restaurant in the Ibiza Castle, called my own Uber, chatted up my Colombian Uber driver in his native tongue (gotta get my reps in when I can), and rolled up just in time to down a touristy cocktail known as a “Pornstar Boob”, which was served in a perky, breast-shaped cup.

Again, Ibiza is like Panama City Beach, but with a castle instead of a Ripley’s Believe It or Not.

Post dinner, we headed further up the castle to a chill bar near the top, where we took cool pics on the ramparts and ordered espresso martinis.

While I had a ticket to a show starting at 1 AM that night, I had low-key planned for today to be a chill day. Between the booze cruise in the afternoon and the Kygo show coming up tomorrow, it would have been responsible to simply go to sleep.

But we were still at the bar as it closed at 1 AM, which made for a very convenient opportunity to “pop by” the club for a bit. Had it been 100% up to me, I probably go to sleep at this point. But I am an easily impressionable young man under specific circumstances.

So, naturally, I found myself ripping a cig before a Diplo concert at 1:45 AM. When in Ibiza, do Ibiza things. What’s more Ibiza than that?

That being said, on my current trajectory of bi-decade Ibiza trips, I’ll probably be back at the same hotel going to the same concerts as a 31-year-old in summer 2028. If anyone reading this sees “Travel Blog 275: Headed back to Ibiza,” please get me some help.

Sunday was the day that I was looking forward to most, because we had a Kygo concert that afternoon. Kygo has been my go-to snow-skiing playlist for the last several years, so an opportunity to see him in concert was a no-brainer.

I spent most of the day doing frivolous work activities (such things are, unfortunately, play an important role in me affording to go to the Panama City of Europe with my friends), alternating between Coronas and espressos as I attempted my best Hemingway impression, before grabbing a light dinner at a café nearby.

I also managed to break a bed during a pre-game.

I’ve broken two beds in my life, neither of which were sexual in manner. The first happened in Gulf Shores, Alabama in March 2016, when a wrestling match broke out between several of my friends and I, and our combined mass broke a bed frame.

I was the best man at my best friend’s wedding in February, and his dad interrupted my heartfelt speech to reference that particular damaged bed incident.

In this second incident, I simply sat down on a bed that a girl was already sitting on, and the bed collapsed. There’s likely a venue for me to file an emotional damage lawsuit against the hotel, considering that, while surrounded by 9 girls, my sheer mass was enough to buckle a hotel bed.

What if I have body issues now? What if I’m perpetually worried that people think I’m fat? These things matter!

Anyway, I shook off my party foul with the opposite of grace, and we ubered back to Ushuaia for Kygo. My night started with a mysterious blue beverage before I regressed to the mean (tequila sodas). At one point, I almost put my 6’7 friend Henry on my shoulders, but that felt a bit hazardous (though I totally could have pulled it off. I hit 365 for a triple on back squat the other day. This would have been nothing).

Post-concert, I once again returned to the hallowed Mexican restaurant from Friday night, ending the trip how it began: chowing down on burritos and coronas after a night in Ushuaia.


However much fun Sunday was, Monday wasn’t.

I was flying out around lunchtime, so I woke up at 9:15, grabbed breakfast, gathered my things, and headed to the airport.

I’ve never been to the Middle East, and besides Israel, I don’t particularly care to go to the Middle East any time soon. But the Ibiza Airport after a weekend of debauchery is the closest thing I’ve seen to a refugee camp.

Thousands of zombie-like Brits and Germans, dopamine depleted after a 72-hour ketamine-induced bender, sprawled out on the floor, sweaty and disgusting, dreading their return to the real world.

I blended in well (minus the ketamine. I told myself going into this trip that anything I hadn’t done by age 26 shouldn’t be done for the first time at 26. Ketamine is one of such things that I haven’t done. Cigs are fine though).

After a weekend in Ibiza, I was happy to head to the beautiful island of Mallorca with my good friend Toni. Toni and I were coming off similar trips. He’d been in Mykonos for a bachelor party with his college friends.

This Mallorca trip was not a “going out” trip. Quite the opposite, it was a honeymoon in a small Mediterranean beach town, except instead of newly-wed lovers, we were hungover grad school friends.

Toni had rented a comically small Fiat 500 for us to whip around the island, and we were staying in the port of Sóller, a small beach town 45 minutes from the island’s largest city, Palma.

When it was time to board my flight, I walked to the gate to see that I would be on a twin-propeller jet operated by Iberia. I didn’t know “real” airlines used propeller planes, and I also didn’t expect to be seated facing two other passengers, and the first row turned around to face the second, but the flight was fine.

30 minutes after I landed, Toni arrived, voice completely hoarse, ready to whip our clown car across the island.

I consider myself a good planner. I know how to find great lodging, from hotels to Airbnbs to hostels. I speak functional Spanish, I can avoid touristy spots (and lean into them, as needed), I figure out the best bars and clubs ahead of time, and I’m generally good at befriending folks wherever I go.

That being said, Toni crushed this trip in a way that I simply wouldn’t have pulled off.

I never would have found Sóller, but it was perfect. The port was built around a near-circular bay, with hotels, bars, restaurants, and shops circling ~300 degrees around the water, before a gap between two cliffs opened up to the Mediterranean Sea. I was the only American in town, as everyone else was British, German, Spanish, and Dutch (and Colombian, including Toni). A small train carried passengers a few miles from the port into the proper town, and hungry diners enjoyed rosé and tapas at various eateries near the water.

It was the perfect European summer getaway. Certainly more wholesome that the previous 3 days.

Upon arrival, we parked the car, checked in, and chilled in the room for a bit before taking a stroll around town. While Toni often acts like an over-sized 12-year-old with a caffeine addiction, the kid does have good taste in wine and food (while I, on the other hand, thought until a few weeks ago that a “sommelier” was a pirate-infested country in northeastern Africa), and he took charge of our dietary plans for the trip.

We dined at a Spanish restaurant near the harbor, sharing paella negra. Afterwards, we enjoyed a much-needed 10-hour slumber.

The next day, I headed to town for coffee and a pastry, and then we jumped in the car and drove to a small town 45 minutes away. Toni had found an old, abandoned fishing village on the water, and we wanted to go see it.

Unfortunately, we didn’t realize that you couldn’t really drive to the village. It was a hilly ~1.5 mile walk, and we were in flipflops. We stopped at the one restaurant in this tiny town relatively close to our target destination and enjoyed coffee, beers, and a brief lunch, then we made our way to the village.

It was HOT, and I was sweating so much that my shirt changed colors entirely within 10 minutes.

Along the way, we passed a family of wild donkeys, and we were a bit worried that they were going to get aggressive with us (we soon realized a baby donkey was nearby, and they were just being protective), and we saw some insane cribs on the mountainside in the middle of nowhere.

Finally, we began our descent towards the water. I was growing nervous, as we had only passed one other group at the beginning of our trek, but we soon reached this weird compound built into the mountain near the water. I thought it was abandoned, but I heard a generator running and peaked in a window to see an older man eating some bread in one of the rooms.

I guess he lived there? Idk.

At the bottom of the compound, there were boat ramps and private boat storage ramps leading the water, and two women in their ~40s were hanging out on a rock near the compound.

Toni and I threw off our shirts and swam around the little inlet. After a few minutes, I asked if his legs were burning. I thought maybe I was having an allergic reaction to the algae in the water, but he said he felt fine.

We climbed on top of a rock, and I noticed that the entire left side of my right knee was beginning to blister up.

“It’s probably a jellyfish,” Toni said.

I swam back to shore and posted up with my book, trying to ignore the itching pain on my knee that was growing stronger and stronger. After ~30 minutes, it peaked, and my knee looked like I had pressed it against a hot stove.

We walked back to the car after another hour (and we passed a sign inscribed with jellyfish drawings, which made sense), and we stopped at a small mountain town on the way back to explore a bit. We grabbed dinner at a restaurant on a hill, and the food was incredible (shout out Toni once again). It was four large pieces of toasted bread, topped with different varieties of cooked pork. Absolutely delicious.

When we got back to the hotel, I realized that I had left the windows down on the car. Somehow, the steering wheel got locked and we couldn’t get the key to turn. Toni Facetimed one of his boys (also, ironically, named Jack) who was apparently a car wizard, he helped us get it working again, and then we showered and headed out for gelato.

On Wednesday morning, we had plans to meet with one of Toni’s Colombian friends, José Maria, and his wife. They happened to be in Spain for a wedding and came to Mallorca to vacation for a few days, so we rented a boat, they picked up paella, and we spent the day on the water.

 José Maria was a big Litquidity fan and appreciated my work.

We spent the afternoon riding around to various beaches and caves, stopping for 30 minutes at a time to swim around and explore. Caves have always been a combination of fascinating and terrifying to me. I feel like people, and especially boys, have an intrinsic desire to explore stuff. If you see a big rock, you think, “I wanna climb that.” Same goes for caves.

We also stopped at the same location where I got stung the day before. No stings this time, thankfully (thought I did see a big boy jellyfish floating around near the boat).

We returned to the port later in the afternoon, and Toni had a work call while I set up in the hotel bar/café to work for a bit (once again drinking espresso after espresso. I love America, but European coffee is leagues ahead of the stuff back home).

That night we had what was probably my best meal in Spain (well, this or a steak at Nacional Barcelona. That steak was incredible). Toni and I split a bottle wine and had grilled octopus and potatoes for an appetizer, then they brought out the best fish of my life. Once again, the kid knows his foods.

After dinner, we headed back to the hotel to get some sleep. Had to be up at 4:30 AM for a flight, not great! Toni was headed to London to meet up with his girlfriend, I was headed to Málaga to meet up with a few of the rugby boys at one of their grandparents’ houses in Marbella.


4:30 came way-too-early, and we rolled out of that room like the walking dead. We reached the airport at ~5:30, parted ways, and then I grabbed some food and headed to my gate. I had a layover in Barca for an hour, and then I sat down at the Málaga airport for a couple of hours to finish some work before ubering to Marbella.

One of my business school friends, Andrew, has a house in Marbella. His family is South African, and his grandparents spend a few months each year at their Spain residence. Six of us were hanging here for a few days: Henry, Ned, Chris, Ian, Andrew, and myself, and the place was incredible. I unpacked and threw my clothes in the washing machine (first time doing laundry in 10 days, much needed), and then we dug into a massive lunch spread.

Afterwards, we ubered to a small canyon/stream thing a couple of miles from the house.

We jumped off some rocks into the water, and swam/walked/crawled/fell for the next hour as we made our way down the stream. I’m pretty sure I rolled my ankle, and I almost got wrecked at the tail end of the journey trying to slowly climb down a 20 ft decline while holding a rope.

We then headed back to the house to nap and rest up before dinner.

Dinner consisted of pizza at the house, and we hung out with Andrew’s grandparents (who were hysterical) for a bit until they went to bed. We pregamed around the pool until midnight before heading to the port to go out.

We bar-hopped a bit, and then found ourselves at a night club around 1. I accidentally shattered a beer (which happened to be Henry’s, unfortunately) as I tried to set my beer down on the bar without looking and managed to slam it down directly on top of Henry’s beer.


At this point I was exhausted, running on 4.5 hours of sleep and failing to nap earlier. Ned called me out for yawning, I accepted that I’m now washed up, and I grabbed Andrew’s keys and headed home.

I woke up at 9:30 the next morning, drank a coffee, and updated the world’s most important daily financial newsletter before crawling back in bed for like 3 hours. Still hadn’t caught up on sleep.

I woke up again around 1, and we made plans to go to the beach Initially, we were planning to hit a beach club, but morale was low and we instead chose to get a casual lunch and hang out in the sand for a few hours. We strolled around the waterfront, stopping somewhere for coffee, then headed back to Andrew’s house.

We chilled in the pool for most of the afternoon, before tuning into a Rugby World Cup match at 8. While there was an initial push to go out that night, everyone was pretty wiped and Ned and I had to fly out in the morning, so we drank around the pool until 1:45 and called it a night.

Now I’m headed to Budapest with a decent night’s sleep and some clean clothes. Not a bad way to end my August in Spain.

Catch you guys later.

- Jack

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