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July 12, 2022

Summer in San Juan!

by Ashley Hesseltine

Back in April/May, I decided that this was going to be ASHLEY’S SUMMER OF FUN.

The first few months of the year were total shit not great for me personally and I didn’t take any vacations, so by the time June rolled around, I was so ready to GTFO of my depression town.

To kick off my two months of traveling (read: people asking me WTF is my life), I went to San Juan on a press trip. I had been to Puerto Rico once before, but only for a day that was cut too short (ugh, cruises AMIRITE?), so I was pumped to go back and experience all the city had to offer sans curfew.

I arrived at the beautiful San Juan Marriott & Stellaris Casino, checked into my room, and immediately flopped onto the king-sized bed (then redid said bed flop four times to get it perfectly natural-looking for Snapchat), and took a pano pic from my balcony so I could #humblebrag about it on social media.


We spent the first afternoon and evening at the resort where the sun was shining, the ocean was crystal clear, the mojitos were strong, the people were friendly, and the food was mucho delicioso (PS, please disregard any Spanish I try to use in this article).

Here’s a mojito on the newly remodeled penthouse balcony (their loss not putting me up in this room).

And here’s the most delicious fresh fish over MOFONGO (a traditional Puerto Rican dish best described as “garlicky plantains”) in the hotel restaurant La Vista Latin Grill…and honestly the best mofongo I had on the trip.


After my mofongo overdose, all I could picture was starfishing on that king-sized bed, but apparently there was salsa dancing to be done.

The Red Coral Lounge in the San Juan Marriott is actually one of the top salsa spots on the island and we quickly understood why.

I even let myself be whisked onto the dance floor, even though I was basically Elaine from Seinfeld next to this pro.

An older gentleman asked one of the other girls to dance and we couldn’t help but notice his command of the room and sick salsa moves given he looked like he might croak at any moment.

Hey now, I know what you’re thinking: “Ashley that’s a really insensitive thing to say about your elder.” Well yeah maybe it would be except for the fact that Chi Chi (yes, that’s his name) ACTUALLY almost died on the dance floor just a few months prior. Yes, that’s right — we got the inside story from the bartenders.

Supposedly he was immobile on the floor with an ambulance on the way, and he came BACK TO LIFE and has been dominating the dance floor ever since with his (much younger) girlfriend, who never leaves home with her “dance kit,” which includes a handheld fan and high-heel shaped flask.


We hung out with them a bit, got some Snapchat footage, and when it was time to say goodnight, Chi Chi salsa danced the whole way out the hotel doors. I made a mental note to dance-exit more often.

And that was Day One.

The next day we toured Old San Juan. We did a historical tour at Castillo de San Cristobal and it was so cool to hear about Puerto Rico’s rich history and how it became part of the US. Even though I tend to zone out on field trips, I really payed attention on this one. (Don’t quiz me though.)

And because we’re bloggers/Instagrammers/narcissists/whatever, we all had to take artsy, “candid” shots like this.

Photo shoots like this are even MORE fun when you’re an awkward person in general and the wind is blowing 93493247 MPH.


We walked the blue cobblestone streets…

We had a pina colada at Barrachina, “The Home of the Pina Colada,” where they make an average of 2,200 A DAY (seriously, that’s what they told me). I am still having a hard time believing that stat but whatever, I’ll drink to it!

And I bought a custom Panama hat that I’m OBSESSED with at a place called Ole Curiosidades — I chose my hat style and ribbon color and the friendly owner fit it to my head (and cut me a deal).

(Not my hat, but wait for it….)

Then we stood in the street for 30 minutes and took iPhone bursts so everyone could get the perfect photo. #DoItForTheGram, y’all.

Old San Juan is seriously so beautiful and charming; you could spend hours just walking around and exploring (and taking jumping pics in the street, obvi).

That evening, we did a hard hat tour of the Hard Rock Cafe, which is opening right across the street from the San Juan Marriott, and is going to be a definite hot spot in town.

After a few glasses of bubbly, we strolled down the street to Cocina Abierta for a private cooking class and upon walking in and reading the menu, I regretted not wearing a more elastic waistband. This was such an incredible experience as we all got a little hands-on action and enjoyed a fantastic four-course meal.

When you go to San Juan (which obviously you will now, duh), definitely dine at this restaurant, cooking class or not.

The next day, we went “surfing.” Why is that in quotes, you ask? Because I wouldn’t call what I did in the ocean that day anything close to surfing aside from the fact that I was attached to a board.

Don’t get me wrong, we had an expert instructor and the waves were significant enough to ride, but I don’t surf, you guys. I’m good at many a few things, surfing and skiing are not on that list. Neither is patience.

But of course I still had to get a photo that made me look cool and somewhat comfortable with a #surfbort because #WhatWouldBeyonceDo?

And I will say, even if you don’t excel (read: totally fail) at something, it always feels really good to try.

After shredding all those sick waves, we went back to the hotel to relax/recover and I got a massage in the hotel spa. I know what you’re thinking — “Oh that sounds nice, massages are great!” Sure, massages are great, but have you ever been oiled up and rubbed down by a smokin’ hot Latin guy?

If not, put that on your bucket list, betches. Shout-out to Carlos for an amazing massage and letting me creepily take his picture (trust me, it really doesn’t do him justice).

Ok, I’ll stop talking about this now before my boyfriend dumps me.

Anyway, after all that excitement, we trekked up through the mountains to the Pork Highway, which is exactly what it sounds like (earmuffs, vegans) — a whole bunch of pig-heavy restaurants in one salivatory spot.

But before you book a flight to this meat retreat, know that it really only pops off on Sundays and many places are closed during the week. But luckily, we found a place to serve us literally everything they had left in their kitchen and all was right in the world.

Highlight of the meal: I asked for hot sauce and this is what I was handed.

A giant Dewar’s jug filled with pepper-infused condiment deliciousness? Try to put that in your bag, Beyonce.

(And yes, that’s my beloved CUSTOM PANAMA HAT!)

We made our way back down the mountain, and chatting over some gelato from the hotel’s cremeria, agreed we had to go out on our last night. We got ready and hopped in a cab for the short ride to Old San Juan, but given it was a Tuesday, there wasn’t much going on (pro tip: downtown only gets lit Thursday – Sunday).

But we refused to take the locals’ recommendations to hit Senor Frogs and pressed on to find the perfect (or just open) place for some cocteles. AND OH DID WE FIND IT.

Sol y Cruz is a three-story establishment of awesome. The first floor, St. Germain, is a bright bistro and bar. The second floor, The Mezzanine is a cocktail lounge with funky armchairs for seating and beautiful, Instagrammable decor.

And the rooftop, Al Fresco, is where we settled for ROSE MARGARITAS (yes, you read that correctly) and lounging under the twinkly lights, overlooking the city.

This was an absolutely perfect trip and I cannot rave about San Juan enough. I highly recommend visiting (and it’s a domestic flight, no customs lines or passports needed!).

I will definitely visit Puerto Rico again, stay at the San Juan Marriott (because mofongo and Carlos), do a “biobay” experience (#BucketList), and of course, master the art of surfing. (JK, no way in hell.)

‘Til next time, San Juan!

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