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A few years ago, my wife and I took a kids-free trip to San Juan, Puerto Rico. While this wasn’t our first “free” trip with miles and points, it was a “surprise” trip where I didn’t tell Carolyn where we were going and one where we bartered airline miles for babysitting
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San Juan as viewed from the fort
Questioned by the creepy guy in San Juan Puerto Rico
We stayed at the Hyatt House San Juan, which was IMO an incredible bargain at only 8000 Hyatt points a night. One morning we walked from the hotel (which was in the Condado region of San Juan) over to Old San Juan, which is about a 2 mile walk. At one point, we were stopped by an older gentleman. Here is what I had to say about that in my original post
…as we were crossing up to Avenida Rivera, a guy came up to us and asked if we spoke English. His English was native, and he proceeded to tell us a story about he was on a cruise ship and he was walking with his dad and they got lost, and then mugged, and the police had taken his dad to the hospital but he needed like 4 bucks to pay this guy for taxi fare (or something). Perhaps I’m just overly jaded, but it sounded a bit fishy, so we moved on and he didn’t pursue us
Other people accosted by the SAME guy
The interesting thing is that in the 2 years since I posted the original article on Old San Juan, I’ve had several comments from people talking about the SAME guy. It’s almost like they run into him, then Google for “creepy guy in San Juan Puerto Rico” (or something), find my post, and share their experiences. Here’s a list of what people have said
I’ve heard that line before in Condado… he told me he was from WI, said his dad was mugged in the hospital and was not very kind.
and
Many reports about this guy on Cruise Critic… he seems to get mugged every time there is a cruise ship in town.
and
The same creepy guy told my husband and I that story. He needed $8 for a taxi to get to the hospital where his dad was.
and
Same creepy guy hit us up tonight, too. Story seemed very off to me. There was also a cruise ship in town. If I were him or his dad, I would check a cruise schedule and avoid being “robbed” again. Creep.
Ever ran into this creepy guy in San Juan Puerto Rico? Or anywhere else? Share your stories in the comments
Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
it is the same with gas station scam of a few dollars for gas. same trick different scenario
You definitely should have helped him. Poor guy has been getting mugged for two years and with his dad in the hospital for the past two years as well, how’s he supposed to afford that?
LOL – I never thought about it like that!!! 😀
I live in Chicago and take the El to work ever day. EVERYDAY on the way home the same meth-head gets on and gives the same out-loud spiel about how he just got out of the hospital and need $6 to get a ticket for a train to the suburbs to see his dying father. Most days he is so cracked out you can barely understand what he says. But I am SHOCKED at how often tourists gives him money. I saw a group of older ladies give him a combined $20….I wanted to yell at them…saying they are just enabling his drug use…but rule #1 on the el is never interact with the crazies!
For every person that sees this for the scam it is i think there are enough naive people that fall for it.
Right – if it didn’t work, they wouldn’t do it anymore
I live in Newark, NJ and the same guy has asked me for money virtually every day for 2.5 years. I never considered it to be content-worthy for a blog (or even a tweet).
I think I can shed some light as yo who he is and what is his purpose. I live in Puerto Rico, and a few blocks from the Hyatt House where you stayed. I’ve been seeing the guy in question for years. He is a heroin addict that asks for money around that area and only approaches tourists since every local knows who he is. There is a place in Old San Juan that is a very well known drug point for heroin and that is where he spends much of his time. But the guy is harmless since the police knows who he is and has been warned that any tourist that complains he will get a nice visit from them.
So if you see him it’s even better to just give him a dollar and be on your way than to stand there and hear his crap. Aside from that, San Juan is right now one of he best travel destinations, and you don’t need a passport.
He works with a woman – who has basically the same story. I was approached by both of them on the same day – and at the end of the day saw them together. In my head they have a fabulous beach house – and live off the goodwill of really dumb folks.
Yup he got us for six bucks tonight, same story near Condado Plaza Hilton. He’s still from WI and his Dad still got mugged and he’s still on a cruise.
Bummer – but it always amuses me to feel like there are other people out there are still people finding this guy and then finding this post
Was just walking around old San Juan today and he gave me the same exact story said look me up looked very American approached us in a alley and we ran across him again asking more people. I gave him some change and he told me to stay away from the blocks near el morro cause that’s where he got robbed. This is very funny now that I know this though that years later and this is reoccuring
Hilarious – it does crack me up (in a kind of sad way)
Damn, I got taken by this guy! I walked from Parque Barbosa in Ocean Park to Old San Juan, tired as hell, and he approached me as I just got to the boardwalk on the East side where the piers start. In his late 50s to late 60s, looking like a tourist, with a Hawaiian looking shirt and full brimmed hat. Approached from behind and the side, walking in my direction, and asked if I spoke English, saying he only spoke “Wisconsin.” Just seemed to be making conversation and said he and his Dad got mugged in a bad area of Old San Juan. I mentioned La Perla, and he said, “That’s it!.” Said they were taking photos at the wall and a guy walked up from La Perla with a gun, hit his dad on the head and took their wallets and stuff. Dad was in hospital, and he needed $8 boat fare from “Pier 10” to get back to hotel somewhere on eastern end of island. It took him ~1/4 mile of walking with me to get to asking for the $8. Didn’t look like a bum to me, so for $8, I thought I’d give him benefit of doubt. He had so many details, and I just thought that he wouldn’t be scamming for only $8/pop. He was very appreciative and said he wanted to hug me (I didn’t). Later, on my way back to Ocean Park, I was walking East on Constitution St. and ran into him walking in opposite direction near the Capitol. I said “What’s up?” He said Dad had heart attack and might not make it, and he was very upset and was going to take care of some hotel business in opposite direction. I asked what hospital, and he named one right away, and said it was pretty bad and he was going to transfer to an inland hospital. Thanked me again, god blessed me, and that was it. I saw someone else mention a similar scam in OSJ in 2010! Can’t believe this guy’s been doing this for at least 7 frickin’ years!
Kind of hilarious (but sad) 🙁