San Juan, Puerto Rico 🇵🇷 Gringo's Guide
A hybrid city — some people consider it a part of "gringolandia" — while others a part of Latin America
San Juan, Puerto Rico is definitely a hybrid city. Some people consider it a part of "gringolandia" — while others a part of Latin America.
It really has a lot of both cultures.
You could consider San Juan a "Latin America for dummies" kind of place. It's definitely more forgiving than the rest of the region for anglos trying to dip their toes in Latin culture.
On the other hand, life in San Juan does come with a lot of the downsides of living in the US you may be trying to get away from.
Overall, San Juan has some definitive pluses — but most gringos don’t like to spend to much time here.
Read on to find out why…
San Juan, Puerto Rico 🇵🇷
Population:
Officially, the city of San Juan has just under 450,000 people living within its city limits at the time of this writing.
However, the city limits are small. When you count the whole metropolitan area, there are almost 2.5 million people in San Juan — making it one of the largest cities in the Caribbean.
Weather:
In general, and as you can see, the climate in San Juan really doesn't change that much throughout the year:
With those temperatures, the humidity becomes really important.
And the good news is that it usually stays under the super-important 80-percent marker. That's a huge deal for your comfort.
It also does rain a fair bit in San Juan, but not enough to make you miserable. Percent possible sunshine is another very clutch statistic. As shown, it ranges from 60-76% throughout the year.
The sun in the middle of the day can certainly feel like it goes through you, though! Because of the low latitude at which the city is located, the UV rays are definitely an issue. Use the usual sombrero/sunscreen/etc.
Why Visit San Juan?
The above-mentioned balmy weather is one of the best reasons to go to San Juan, as the city has great beach weather.
In addition…
You'll be using USD as a currency
You will be experiencing Latin culture in the middle of US-style amenities
The day trips around the island are spectacular
95% of the time, you can get by with just English
Overall, most people visit or stay in San Juan, Puerto Rico for one of two reasons:
Beaches
Taxes
For a vacation, San Juan is an actual “beach city” with great beaches in the city itself.
For long-term living, you generally only live here long-term for the tax benefits as a US citizen.
Punto.
Getting There…
You'll almost certainly be coming into Luis Marín Muñoz International Airport.
This is one of the easier airports to get to in the world:
Just to summarize, there are tons of destinations to and from San Juan. However, the majority of them are from the USA and the rest of the Caribbean:
All major US cities, basically anything with a population of over 4 million or so, are directly accessible from San Juan.
You can hit the following Caribbean airports directly from SJU:
Saint Martin (Dutch)
Saint Thomas
Saint Croix
Saint Kitts
Dominica
Saint Barthelemy (Guadeloupe)
Beef Island (BVI)
Virgin Gorda
Anguilla
Santo Domingo
Punta Cana
You can also go back and forth directly from Toronto and Montreal. In Mexico, there are direct flights to Cancún. You can also reach Panamá City and Bogotá directly.
The only direct European destination is Madrid.
Flights are frequent and tend to be on the cheap side, unless you are trying to go during peak season.
More info found here.
Best Neighborhoods in San Juan 🇵🇷
Naturally "la gracia" of living in San Juan is to live on or very near the beach.
This means a narrow strip of land stretching from the famous Old San Juan down to Carolina in the east:
I personally feel Old San Juan is the nicest place in town. Others seem to agree with me, because it's the most expensive — and super touristy.
The colonial architecture has been beautifully preserved, and it's where most of the city's best nightlife is located.
The only downside is that there isn't the best beach access there.
To be right on the main beaches, you'll have to go to Condado or Isla Verde.
Condado is more upscale; Isla Verde is kind of more middle-class. I still would prefer Isla Verde, however, because the beaches there have nicer sand. Isla Verde is also right now the safest neighborhood in the Greater San Juan area.
Other decent options include Isla Grande and Miramar, which put you striking distance from both Condado Beach and Old San Juan.
Neighborhoods to Avoid
The first place I want to put adventurous expat readers on alert about is "La Perla", a colonial neighborhood on the western edge of Old San Juan.
This place used to be crazy back in the day; it's not as dangerous as it used to be but it's still controlled by drug gangs, and it's far from safe. Especially intrepid expats may find the place to be entertaining, but bring your ghetto pass if you go!
There is also a beach here, but it's small and rocky.
If, for whatever reason you want to stay somewhere south in San Juan, definitely avoid staying in the following neighborhoods:
Vega Baja
Puerta de Tierra
Piñones
Juntas
Santa Lucía
Capital
Chimbas
In general, there is very little to do as you go further south in San Juan. Some neighborhoods are OK as far as safety, but they're just boring and inconvenient. You'll be stuck in traffic most of the time (San Juan's traffic is not a joke) getting back and forth to places you want to be — places you should just stay near in the first place!
Places to Stay in San Juan, Puerto Rico
I've said in previous articles that some towns favor Airbnbs and others favor hotels. San Juan is one of those where you can split things down the middle.
If you want to stay in Old San Juan, it's going to be expensive any way you slice it. Naturally, Airbnbs will still come out cheaper, way cheaper if you are planning on a month or longer stay.
Airbnb Options:
This place is right near the heart of the neighborhood, and is pretty state-of-the-art. I'm not so wild about the spiral staircase; otherwise it would get full marks.
If an Airbnb in this neighborhood is going for under $3k in USD per month, be careful, and try to find out what's wrong with it before pulling the trigger.
Here's an example of a great deal on an AirBnB in Condado.
It's a nice spacious one-bedroom with a dedicated area for working and a huge monthly discount.
I also found this gem in Isla Verde. It might be too small for some people, but I think the location more than makes up for it!
If you're looking closely at the maps, you can see that Airbnbs really close to the water are rare. In fact, the Isla Verde map shows the only four that are even currently available!
Generally, if you want better beach access, you'll want to get a hotel room.
Hotel Options:
My pro-tip for people who want to stay in San Juan, especially short-term:
Check out the ESJ Towers in Isla Verde
Once again, this is all about location, which is super clutch in a city like San Juan.
You are literally walking distance from much of the best of what the city has to offer here.
You can get up to a two-bedroom suite at this place, although it will cost you a pretty penny if you want to stay long-term. You can save almost half that amount by getting a studio or one-bedroom. I would recommend paying the tiny extra charge for the sea view, though.
Other recommendations include:
Costs of Living in San Juan, Puerto Rico
This is NOT a cheap city whatsoever.
The combination of being part of the USA, mass tourism due to beaches, and tons of rich expats buying their time here to avoid taxes = expensive as hell.
In the opinion of your humble author, you would be hard pressed to live here under $5,000-6,000 USD a month on a short term rental — if you wanted any social life whatsoever.
All prices in USD below…
Airbnb Apartment in Best Area: $2,000-4,000+
Hotel in Best Area: $5,000+
Maid: usually included
Grocery Store: $900-1,200
Eating Out / Delivery: $800-1,000
Gym: $75
BJJ / MMA: $150
Partying / Dating / Social: $1,000-5,000+
Cell Data: $50-100
As you can see, this is far from a budget travel destination ;(
How Safe is San Juan, Puerto Rico?
As far as comparing San Juan to literally everywhere else on the planet, I'd say it is very close to the median line for personal safety. I've been in much more dangerous places, and also in much safer.
The good news about San Juan is that the vast majority of the crime occurs in areas that are easily avoidable.
Just don't go slumming in this town, and your safety factor increases exponentially.
Also, if you decide to explore the rest of the island — which can be incredible — stick to the coasts and avoid the center of the island, at all costs. The center of the island is known for mayhem in general, and a lot of people there don't take kindly to outsiders, speaking from personal experience!
Overall…
San Juan, Puerto Rico occasionally makes the lower end of the “50 most dangerous cities in the world” list.
But the nice areas of the city are overall quite safe.
Dating Scene in San Juan 🇵🇷
I'll start off on a bad note:
You will have tons of competition dating in San Juan, Puerto Rico.
Since the place is super accessible for Americans, you will be up against many of them on the dating scene, all year round.
You won't get any points for being exotic here, almost no matter where you are from on Earth, in fact.
San Juan gets people from all over as tourists and even long-term stayers as a matter of course.
Having said that, however, there is still lots of hope for the intrepid and adventurous expat type who wishes to succeed in San Juan. People here are still very friendly — although not as friendly as, say, Colombians, Mexicans or Brazilians would be.
Also, there's lots of demand as well as lots of supply on the local scene. San Juan is teeming with all kinds of women from all walks of life. There's no shortage of 9's and 10's walking around this city, especially in the areas you are going to be frequenting.
Here are some things you can do to stand out among the crowds of dudes you will be going up against for female attention:
Dress to impress — a surprising amount of people don't even do this! Just don’t look like the typical gringo.
Go to local cultural events to meet women, not just all the typical nightclubs. There are lots of these all around.
Corollary to that, learn about the island's culture and history, backwards and forwards.
This leads into the most important point of all. Speak excellent and elegant Spanish to impress women in San Juan.
I'll elaborate this point in the next section…
Do You Need to Speak Spanish in San Juan?
PRO TIP:
Puerto Rican women are — against all silly stereotypes — pretty well-spoken, well-educated and cultured.
Don't be fooled by the way artists like Bad Bunny talk; that's literally the most ghetto segment of Puerto Rican society being pushed forward there!
Puerto Ricans are also — this time in line with the stereotype — famous for being touchy and hot-headed. This is something you can use to your advantage, as many non-savvy suitors will be crashing and burning because they accidentally offended a girl.
In my mind, the secret to success on the San Juan scene is, despite the fact that you really don't need Spanish to get by — is to get your Spanish good. I mean really good, not just conversational.
Forget about the San Juan they show you on TV. In real life, women in this town will melt over a well-presented guy who can speak high-level proper honorific Spanish.
Be that guy. Full stop.
Absolutely need to speak Spanish here to get the best our of San Juan.
P.S: Luckily, learning Spanish is easier than ever before…Just click here.
Nightlife in San Juan, Puerto Rico
I could seriously sit down and write for days on end about the nightlife in San Juan. It's nothing short of epic.
Most of Latin America really knows how to party. But, I would put San Juan up against just about any other Latin American city when it comes to things to do after the sun goes down.
You have tons of live music venues here, discotheques blasting EDM at all hours with world-class DJs, other cultural events of every nature, cool local dive bars, you name it!
Here are a couple of quick recommends for what I think are top spots right now.
Toxic Nightclub - Condado — for the hardcore partiers. Doesn't even open till 10pm, goes all night most nights. Packed with beautiful women.
The Cannon Club - Old San Juan — great classy place for dinner dates. Live jazz and piano bar, depending on the night.
101 East Bar and Lounge - Isla Verde — more of a chill lounge atmosphere. Never closes. Hands down the best time in Isla Verde.
Pani Agua - Old San Juan — located right off the historic Plaza de Armas. You can get food and drinks here, but I'm including this because I had the best hookah I've ever had in my life there.
As always, ask around for up-to-date recommendations on nightlife — as it can change month after month.
Exploring the Rest of the Island…
Puerto Rico is small enough that anywhere you want to go on or even close to the island is easily a short day trip.
As such, there are lots of things you can do for fun date day trip action starting in San Juan. Not all of them are worth it, though.
As I mentioned previously, the center of the island is a no-go zone, even for the intrepid and adventurous among us. It's just too dangerous.
There are also cities like Arecibo where there's really not much going on. Unless you are visiting somebody's family or something, you're going to be bored.
Here are some of the best day trips you can go on from San Juan:
Isla Culebra
This place is drop-dead gorgeous and has an absolutely first-class amazing beach!
Bring things like snacks in advance; as you can see, the place is not very built-up.
Also, it only costs $2USD to get there. Because of that, the boats are booked up well in advance. You can't just show up and get there, unfortunately.
Vieques
This used to be a US Naval base until recently; popular opinion caused the gringos to pack up and abandon the place.
It used to be used for weapons testing, but you'd never know it now. The beaches here are numerous, pristine and varied. Most of them are the gorgeous white coral sand I love:
There's also a black sand beach for variety, though:
Vieques is also much more built-up than Culebra. Here you can find nice hotels and spas, and it's not a bad idea to stay the night.
It's also cheap to get to by boat, and the boats are also booked up way into the future. Plan ahead.
Ponce
Ponce is Puerto Rico's second-largest city. While it doesn't have the cosmopolitan vibe of San Juan, it has more traditional charm and culture.
It also has a very picturesque colonial downtown area. It's not as big as Old San Juan but it's been preserved much better:
How Long Should You Stay in San Juan?
If you go to San Juan, you should give it at least a couple weeks.
There is no real limit on how long you should stay in San Juan. People who really like the vibe could easily make this place a home base for an extended period of time.
In fact, many Americans especially may considering relocating indefinitely for reasons explained right below:
Tax Breaks for Americans in San Juan…
This is the MAIN reason while many wealthy Americans live in San Juan.
There has been a lot of buzz surrounding the issue of possibly finding your way into a tax haven if you live in San Juan. I obviously have to comment on this, or the article wouldn't be complete.
The rumors are true, and you can save money off of your tax bill by relocating to San Juan.
However, there are a lot of messy strings attached to this offer!
First off, residency requirements are very strict, and the IRS lately has been enforcing them with an iron fist.
San Juan has to be your primary residence.
Not only do you have to stay there at least 183 calendar days of the year, you have to not have stronger ties to anywhere else in any other way, shape or form. Right away, this clashes heavily with my nomad spirit. It probably does with yours too, dear reader!
Also, the law is designed not to help you out as an expat, really. It's mainly there to get people to invest heavily into Puerto Rico. As such, the real tax benefits only kick in if you do just that, invest heavily. Don't expect your capital gains taxes all over the world to drop down just because you set up shop in San Juan.
The real economic incentives only kick in if you actually create jobs for Puerto Ricans. Keep that one in mind before jumping into any type of investment.
However, there are obviously many loopholes here ;)
Finally, the law could change at any time.
The Puerto Rican legislature is famous for going back and forth on issues like these. Even if this initially works for you, you are always one bad election away from the law being revoked and your tax liabilities going back through the roof!
For more information on the law everyone is talking about, Act 60, you can read up on it here at the source.
San Juan, Puerto Rico 🇵🇷 Overall
San Juan is an excellent fit for people who:
Want a Latin "vibe" and don't want to give up anything from their home country in terms of infrastructure, etc.
Are still working (hopefully hard) on their Spanish
Like some things about Latin America but not all
Have deep ties to the US and want to get back and forth quickly and easily
The flipside to all that is that you won't get the bang for your buck you would get in any number of Colombian cities, for example. Really, San Juan is not a cheap place to stay, especially when you look at alternatives.
A lot of people might want to use San Juan as a sort of "stepping stone" to start to get acclimated to Latin culture. From there, you can then keep heading south to the rest of the region. This is not a bad strategy at all!
My home base is, and will be, in Colombia, but I like going to San Juan from time to time for a change of pace, even though it's expensive. It's nice to catch a short flight there and experience its unique hybrid culture.
In short, San Juan has a lot going for it, and it's definitely worth checking out!
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