Where to spend a month or two this winter

Old Oct 21st, 2014, 05:58 AM
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Where to spend a month or two this winter

I'm considering spending a month or two someplace warm this winter, and would like to solicit ideas on possible locations in the Caribbean. I telecommute, and would plan on continuing to work while away, so this would be more a relocation than a vacation per se. I'm not a tourist compound kind of person, so am not looking for a condo rental in some big development for foreigners. Ideally I'd like to find a reasonably priced (less than $2,000/mo) rental (with kitchen, internet) someplace close to or on the beach, preferably also close to a jungle, and in or within walking or bicycling distance of a town. I'll be alone, so safety is a concern, as is not too, too much isolation(!) A place with an expat community or the opportunity for organized excursions would be good. Proximity to snorkeling, preferably from off of a beach, would be fantastic, as would some interesting (but benign) wildlife (I'm a biologist). Easy transportation to/from an airport would also be nice. Is this too much to ask?

Probably the closest I've found so far is Cahuita/Puerto Viejo in Costa Rica, both beautiful places, though a bit difficult to get to and maybe a bit small to spend more than a few weeks in. I'm thinking there must be somewhere in the region that fits the bill, but after weeks of searching various forums and websites my head is spinning, so I figured I'd ask those in the know.

Thanks for any advice.
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Old Oct 21st, 2014, 07:59 AM
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I know this is on the Caribbean forum, but would you consider Mexico? It has everything you are looking for.
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Old Oct 21st, 2014, 09:04 AM
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Regardless of where you choose make sure you check and understand the laws of the country/island where you are planning to stay. Many, if not most, Caribbean Islands have strict laws that do not allow non-locals to work without first getting a Work Permit (often very difficult to get and almost impossible for a short term position) and some of those countries/islands consider "telecommuting jobs" the same as working in that particular country. Now, some people will give you anecdotal information saying they "worked" while visiting some Caribbean island on vacation without experiencing any dire consequences but that doesn't mean what they did was legal. Islands are small and there are very few secrets & lots of gossip, especially among those who are staying for extended periods. The last thing you want is for one of the locals to get wind that you are "working" and report you to the local Labor Department - it's the quickest way to get deported.

Now for some useful info - if you are a US citizen consider Puerto Rico, Culebra or Vieques and the US Virgin Island as you will already have citizenship/work status so that shouldn't be an issue and on those last two islands you can find everything you are seeking (except PR which is not noted for great snorkeling).
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Old Oct 21st, 2014, 02:15 PM
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Good point! I hadn't thought about the legal ramifications. I've had working sojourns in Europe without problems, but I can see how that'd be different. A bit funny that countries would make it difficult for people to create little pipelines of American dollars to their shores!

Thanks for the suggestions. Culebra seems very nice (if a bit expensive), though it seems you'd need to rent a car there, something I'd like to avoid.

Thanks again for the tips.
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Old Oct 21st, 2014, 02:17 PM
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Suze - yes, Mexico would be a possibility. In fact Merida was kind of a fallback. No beaches there, but plenty warm, and a really beautiful town. Any other suggestions?
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Old Oct 21st, 2014, 02:33 PM
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Well I personally am crazy for Puerto Vallarta. I travel there solo every year and rent an apartment. You could find a studio in your price range somewhere near the beach. The international airport is right there within the city. Safety is not a concern in PV. Excellent public transportation and easy walking around town.
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Old Oct 21st, 2014, 02:34 PM
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When I first mentioned Mexico, I was more thinking the Caribbean side since that's what you were originally seeking. somewhere around Playa del Carmen. but I've never been on that coast myself, and realized after rereading your post, that PV does pretty much fit (lol)!
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Old Oct 21st, 2014, 05:18 PM
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OP commented - "A bit funny that countries would make it difficult for people to create little pipelines of American dollars to their shores!"

It has nothing to do with "creating a pipeline for American Dollars" but rather protecting jobs. Unemployment is high on many islands and the local governments don't want foreigners taking jobs away from the locals.

Anyway, good luck in your search.
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Old Oct 22nd, 2014, 02:19 AM
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To add, work permits are hugely expensive and hard to come by (think $3000-$7000 depending on job, or have requirements of having an Islander partner which can get complicated)

If you mean this winter, you're probably too late-- I've seen them take a year to get

They are in no hurry to make it easy to let you work (even without getting paid) as they have to protect their own first (as it should be)

Another huge obstacle for you is budget-- most expensive time of year that is mostly sold out already! Even bottom of the line places go for about $2000 a week-- most beachfront places go for $9000 a week on most islands.

Most islands, catch22-- towns are away from beaches, so you'll need a car if there for that long

Central America might work, it's overall cheaper, but I still think you're late in looking for this winter, especially if work permit will be needed
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Old Oct 22nd, 2014, 02:28 PM
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If your timing is flexible rents decrease by almost half after May and stay that way thru October in Puerto Vallarta (low season) vs (high season) of November thru April.
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Old Oct 22nd, 2014, 07:08 PM
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Thanks for all the replies. I hadn't really thought of the Pacific side of Mexico - I've never been there - but might be worth checking out. And yes, I'm starting to realize that it might be a bit late to be looking for this winter. And yes, prices during the winter do seem to be pretty high. From my experience in Europe I was thinking $2,000 would be a fairly easy target to hit.

The work permit situation is certainly the thorniest. After RoamsAround's comment I did a little research, and it certainly isn't as simple as I naively thought. By the way, my comment regarding pipelines of American dollars just referred to the possibility of attracting telecommuters - with their own jobs - to places that would probably welcome the influx of cash. I know some US cities are starting to figure this out; i.e., that there is a growing chunk of the workforce that can work wherever they want, and will bring their own jobs (and salaries) with them. It would seem beneficial to countries to cotton on to that fact, too. There is nothing to lose, and everything to gain from attracting telecommuters, I'd think.

Thanks again for the tips, they've been very helpful. I might check out Puerto Vallarta to see if it's feasible. Or I suppose it might just be the warmest part of Europe I can find!
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Old Oct 23rd, 2014, 05:33 AM
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Again, regarding your "pipeline of American dollars" comment - While your argument may seem logical to a non-islander you have to view it from the "local government" point of view. They would rather have that "telecommuting job" filled full time by a local rather than a part-time foreigner.

That way all the "cash" the worker receives as compensation stays in their country or on their island. This may not seem logical to you but as many of us Ex-pats who live in the Caribbean say - this is a "logic free" zone. The reality is the majority of the laws are designed to protect locals so they can control the island's destiny how they see fit. They want the tourists to come, spend their money then go home.

By the way, there are similar laws regarding foreigners working in the US (although the current administration doesn't seem to want to in force the law - but that's a topic more suited for a discussion on Fodor's Lounge).

Anyway, enough said on this topic.
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Old Oct 23rd, 2014, 06:38 AM
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Maybe it doesn't fit for your particular request this time, but the Pacific coast of Mexico is wonderful. Definitely keep it on your radar for the future.
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Old Oct 28th, 2014, 02:20 AM
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Have you considered Puerto Rico? That would eliminate all the work/visa issues and as an added bonus your cell phone and other technology will likely work without additional roaming or international charges, banking/money is seamless, and even outside tourist areas people speak enough English so if you do not speak Spanish you can converse. We did a bit of exploring of the island last Jan and it is an entire different world outside of San Juan - wondering if you could find a non-touristy rental in some smaller town on the southern or western part of PR. The interior mountains are full of foliage (including a rain forest) and probably wildlife that will not eat you.
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