Help me decide where to live in Latin America/Caribbean this winter
September 4, 2018 1:36 PM   Subscribe

Looking for somewhere warm and cheap to work remotely for 3 months, this winter, in Latin America or the Caribbean. Having a hard time narrowing down my options. Please advise! (Criteria below)

Hey there,
I'm an English-speaking 26-year-old male in the USA, looking to escape the cold this winter. I want to move somewhere for 3 months (Dec-Feb) where I can work from my laptop, outside coffee shops. And live cheaply and safely. It doesn't need to be a huge city with a ton of activity. But amenities are nice.

I'm thinking Latin America or the Caribbean at this point (SEA flights are too expensive, so that's off the table).

I've been struggling to narrow down my options, and would really appreciate some help; I would love to decide on a country, and then a city, so then I can finally do specific research on forums (eg. choosing a neighborhood, etc.) and get in contact with locals online before I arrive on the ground.

Here's my criteria for the city/town:

-You can survive (eg. buy groceries, eat out) with little Spanish (obviously I will make some effort to learn Spanish, but I will still suck by the time I arrive)
-Average daytime temperatures of 75-80˚F (23-26˚C) in the Dec-Feb months (80s is too hot, 60s is too cold)
-Centrally located apartment (a studio is fine) for <$600 USD/month
-Walkable, bikeable, or a good transit system
-Low crime, no political unrest, no hurricanes, etc.
-Cheap flights (so, not South East Asia)

Bonuses (not mandatory criteria, but would be awesome):

-Lots of universities/intellectuals/arts and culture
-Lots of young English-speaking women (tourists count)
-Fast/reliable internet
-Good urban planning (use of green space, not too many parking lots, mixed-use spaces, not too crowded)

So far, I've managed to eliminate some countries based on my criteria: Belize, Venezuela, Trinidad/Tobago, Nicaragua, Bahamas, US and British Virgin Islands, and Argentina.

Help me eliminate more! (Or tell my why I should re-consider one of the above countries)

Recommendations? Thank you SO MUCH for any help you can give!
posted by TheOptimizer to Travel & Transportation (15 answers total) 8 users marked this as a favorite
Cusco Peru or Sucre Bolivia
posted by sandmanwv at 1:45 PM on September 4, 2018

This link will help you with your temperature ranges.
posted by Homeboy Trouble at 1:54 PM on September 4, 2018 [1 favorite]

Have you narrowed down which of these places you can be in for 3 months with your citizenship?
posted by k8t at 1:58 PM on September 4, 2018 [8 favorites]

Came in to say more or less what k8t said - checking out what visas you’ll need for these countries and how working remotely in them may or may not affect you for tax purposes are unromantic but important parts of narrowing this down.
posted by penguin pie at 2:58 PM on September 4, 2018 [3 favorites]

Hurricane season will be over by then if that's why you are ruling out the islands. I'd personally stay on the islands if I only had three months. Very likely Grenada or Grenadines or maybe the Dominican Republic because I hate tourists and they are a bit less touristy. If you have a higher tourist tolerance or want an expat culture somewhere like Roatan or Bocas Town in Panama might suit.

Keep in mind you are going down there prime time and the rise of AirBnB and VRBO has definitely reduced the number of cheap pension rentals though.
posted by fshgrl at 4:18 PM on September 4, 2018

Maybe a secondary city in Chile? It will be summer there, so the weather will be pleasant, though you might compete with holiday makers in the coastal towns in terms of cost of lodging. But, like, La Serena or Valparaiso might be lovely.

Oh, Mendoza, Argentina is nice in their summer. Argentina has had issues with economy and crime but Mendoza is a smaller city. Maybe a bit warm though.
posted by vunder at 4:21 PM on September 4, 2018

Oh, Panama: Maybe Boquete?
posted by vunder at 4:22 PM on September 4, 2018

La Fortuna, Costa Rica (might take a bit of looking to find cheap rent, it's a popular place)
posted by fingersandtoes at 4:40 PM on September 4, 2018

San Miguel de Allende in Mexico ticks off a lot of those boxes -- it's known as an expat place so you can definitely get by with Spanglish, and there are plenty of English-speaking people around. Daytime weather is right in your range (though it gets chilly at night). Lots of AirBnBs to choose from, and a cursory glance shows me many in your price range. If you stay close to the center, you can easily walk lots of places, and taxis are dirt cheap. For food and drink you can go to very cheap places for locals or splash out, but when we were there, we had an absolutely lavish meal for three that was under $60. Highly recommended!
posted by BlahLaLa at 5:26 PM on September 4, 2018 [1 favorite]

Why not Puerto Rico? There will be no visa problems, the weather is fabulous and the populace, while always very welcoming to tourists IME, will be especially grateful to have you spend the winter there. Here is their tourism page regarding Hurricane Maria recovery.
posted by DrGail at 5:48 PM on September 4, 2018 [7 favorites]

Buenos Aires or Santigo sound about right, but I would avoid Bs. As. at that time. The weather is like swimming in soup. Santiago has a lot of cool culture, things to do and cafes with much cooler weather. I know a lot of people like the warmer beach town but I'm kinda partial towards the Southern Cone and it's more European feel.

I like Bogota too, but there may be more issues with language there. I feel comfortable there but I might feel a little constrained getting around town with the horrendous traffic and areas where safety is still a concern.
posted by Che boludo! at 6:46 PM on September 4, 2018

Mérida in the Yucatán is nice in winter.
posted by vunder at 8:47 PM on September 4, 2018

I would say either Puerto Rico, or Ecuador. if you do choose Ecuador we could have a mini-meetup in Dec as we are having xmas vacation there :)
posted by alchemist at 3:25 AM on September 5, 2018

A point I want to make about internet access is every place will say they have (free) wifi but actual speed will be abysmal. (Download speed less than 1 Mbps, true story.) If you are depending on it for work, check out travel routers, wifi extenders, and USB wifi dongles bought incountry.
posted by TWinbrook8 at 6:53 AM on September 5, 2018 [1 favorite]

Merida is great but it is boiling hot even in the winter, 90s and humid.
posted by wnissen at 8:47 AM on September 5, 2018

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