I bought a villa in Turks and Caicos, so yu can guess my pick. Although your picks are awesome.

You might want to consider Hawaii and St John, as one is a US state, the other a US territory.

Before you decide, you HAVe to consider the following things:

Visit all and then decide
Consider all local laws
Consider standard of living, always 2-3 times as much for less comfort
Maintenance is brutal in tropics, things rust out and break so much easier, longer to fix as waiting for parts

Most islands require work permits. Usually renewed at $9000+ annually
Most islands require you can do a trade that current islands can't, they have first rights
While most islands wifi works fine, it's prone to more outages than stateside

It's against most laws to even work for free a single day without permits
Permits can take forever to get (why should they be in any hurry to help an outsider out when they have their own problems to deal with?)

Work permits are not guaranteed and they may decide not to renew, or take time to do it

With Visas most times you have to be able to leave every 2-3 months for a couple of days, and air is outrageous.

You should go where you want to live for a month, away from tue beach, to see what living there is truly like, not just a s a tourist with a dream

Does it work out? For many yes, others no. It's a terrific thing when it works, but you have to put thought intovit and not just say, I just want to pack up and live at the beach.

If I had lots of money and there were no strings attached, my pick would be Grand Cayman.

Hawaii is the easiest if you are US citizen. St John the second easiest, again because it's officially part of the US.

For any of the other islands you need to check all the red-tape about permanent residency.

Have you ever spent extended time in the Caribbean? Island life is not for everyone.

Myself, I'd move to Hawaii, because I love it there and think it would make for the most realistic permanent move.

I'll assume you are a US citizen. If so, you'll find it infinitely easier to relocate to Hawaii, Puerto Rico, Culebra, Vieques or any of the US Virgin Islands as you'll already have residency and work status. To live on any other island you'll be subject to the immigration and work requirements of that particular island.

As a general rule you cannot just show up to live/work. Residency often requires a minimum investment of a large some of money (think in terms of US $300,000 to $500,000) in real estate or a business that supplies jobs for locals. Having residency does not automatically give you the right to work (even if you "telecommute" to a job back in the US). For that you'll need a work permit which can be difficult to get. Blamona gave you some good general info but you'll have to check out the laws on each island as they can vary since each island is an independent nation.

If you are considering moving to an island go to www.vimovingcenter.com - it's a website dedicated to living and working in the USVI's but much of what is written there applies to any Caribbean island. There s so much info on that site it will take the better part of a month to read everything (and you SHOULD READ EVERYTHING). There's also a very active form (with thousands of threads) answering every question you may have and hundreds more you haven't even thought of yet.

Also, get a copy of "The Settler's Handbook" (on Amazon.com or on the VI website I mentioned) it's a must read for anyone contemplating moving to an island.

Now, Hawaii or Puerto Rico may be your best bets if you need reliable high speed internet as the type of service will most closely match what you have in the US. Internet can be "spotty", slow and sometimes "non-existent" on many islands. Research that very carefully before you make any final decisions on where you relocate.

Also, do make a pre move visit to any island you are considering. Go for several weeks, not as a tourist but rather stay in an efficiency unit doing everyday chores. Try to live like a local - do grocery shopping, check out banking, utility costs and the logistics of paying bills, etc so you get a feel for what island life is really like. Take it from someone who lives in the Caribbean, it is not all palm trees and pina coladas. Island life can get very frustrating and it is not for everyone.

Lastly, make sure you fully comprehend the Catch-22 of island life - living expenses can be quite high compared to main land US and wages are often a lot lower. If you relocate to the islands and don't have a significant increase in your annual income you'll have to significantly reduce your lifestyle.

Good luck following your dream.

Well, the 10Mb internet will be a deal breaker in the USVI. Also you have to consider inconsistent power. The USVI or Hawaii are the easiest for US citizens, Puerto Rico if you speak Spanish. RoamsAround's advice about the VI moving center is good, just ignore the snarky responders there.

blamona, what part of the island do you live in?

I'm considering T&C slightly more than the other three destinations simply because of the attractive real estate prices. It's also easy to obtain the residency permit vs the Cayman residency that requires you to invest $750,000 in a property on Grand Cayman.

Here is what $400K can get you in T&C (what do you think of this neighborhood, blamona?):
http://www.tcrea.com/ViewDetail?id=1200153

Here is a shed in St. John for the same price:
http://www.americanparadise.com/view.php?list_number=11-277

I also don't think that the T&C work permit is an issue since my internet business runs on autopilot, and I don't have to work in T&C.

The area is good, but not my favorite neighborhood.

While you might not have to work in TCI, will you have a bank account there? If yes, then you'll probably have to have a work permit. Not entirely sure, but I think just depositing monies counts! Another thing to consider, your home is your office, so that might be considered working there too. Only way it's not, is monies made get paid through the States. This for Turks is consided a fine line. There are tons of "Internet" jobs there, and I can only assume they will give you a hard time about it.

Here's a start:

http://www.immigrationboard.tc/go/en/Work-Permits--page.html


Both are 2 completely different islands.

There are many expats in TCI, so it works for many.

TCI is in transition, they are holding elections in November. Currently they are being overseen by Britian. Currently I think the investment is $500,000. After that, you still pay for residency ($3000 per person?) .

Contact immigration at the link above to see if you still need a work permit. I do think they will consider you self-employed and still require some type of permit to do so.

I don't mean to sound so negative. While I don't doubt that if determined it will be successful, I don't think many investigate thoroughly what it's really like. It's a terrific life, but much harder than people assume. And a lot more work! If computer crashes for example, much harder to repair when you have to wait for parts to come in (or go to Miami shopping).

Living expensives are 2-3 times what they are in the States. Food is extremely expensive. Persons living there pay $250 monthly p person just for the right to use the hospital. The wear and tear is much more than expected in the states. Import taxes on everything you bring in are huge. In April, they are inducting a VAT tax, we will see what this does to business.

Roams, thanks for the Settler's Handbook suggestion. I, actually, got this book about a year ago when researching all island choices. I'm prepared for higher costs of living.

Blamona, can you suggest 2-3 Provo neighborhoods that you like?

Also, my understanding is that in order to obtain a T&C Permanent Residency Certificate, the minimum invested amount should be $250,000. But maybe that's some outdated info: http://www.resortsinternationalgroup.com/node/44

By the way, does T&C (or St. John) have any neighborhoods connected to a central sewer system?

T&C users klagesters I assume St. John is similar

My favorite neighborhoods are Leeward and the little cul-d-sacs off of Grace Bay Road

For the permanent residency certificate though, you do have to annually renew and pay for it. I looked into it lately and all it does is let's you use belongers line at immigration and makes it easier to open a bank account.

Would you be getting a mortgage there? It's actually extremely hard and long time process. Rates are higher for outsiders, and they will only lend 80%. Yu also still have to have enough cash for the one time stamp duty, currently at 11%?

It's my understanding they raised the minimum rate. I thought it was closer to $500,000.

When we bought our villa we meet the requirements, but did not pursue as the annual fee did us no-good.

If serious, you should rent for a month and live like a local. Do your homework from there. You will find no one answers emails like yours, most aren't serious. So you really need to do that in person. You will find you waste days just getting one little thing done. (1 signature to extend my stay took me 4 hours for 3 days in a row).

I can't stress enough, no one will give you answers until you're there in person. You won't be taken seriously unless you're there in person. I have found this to be "island life" and true on most islands.

Kauai - Princeville or Hanalei, no question. I also really loved Kihei on Maui. Practically, if I was moving to Hawaii, I would probably choose Honolulu with big city amenities, shopping, most non-stops to the mainland.