Condemned to an island paradise

You are being given enough money that you can retire. But the eccentric billionaire that gives you all this money has these unusual conditions:
You have to live the rest of your life on an island. You are allowed to take two (non-consecutive) one-month vacations ever year for the rest of your life, but the other 10 months have to be spend on the island. (The vacations can be taken wherever in the world you want.) From your island, you can take a boat to another island but you have to be back home within 5 days. Unlimited 5-day trips per year, but each 5-day trip must end with you going back to your main island, and staying there at least 7 days before you go on the next boat trip.

Oh, and to avoid the nitpicking about the word “island”, the island has to be smaller than Sicily, i.e. 25,000 km[sup]2[/sup] or less. The islands you get to visit with your five-day boat trips also have to be less than 25,000 km[sup]2[/sup].

Which one do you pick, and why? I’m planning my life after I win the lottery.

My first choice, without doing a lot of research in the matter, is going to be Tahiti, because my cousin told me once that he had the best vacation of his life in Tahiti, and I have never met anyone who’s been to Tahiti and regretted it. I would need to convince my wife, but I know she likes warm places, so that shouldn’t be too difficult. I would want to check on the availability of high-speed internet access over there first. :wink:

Does anyone know if I could get to these other nearby islands with a short boat trip?

I am planning this for real. There a whole bunch of good choices out there. Your question simply isn’t that difficult for an introvert like me. There are thousands of islands in the Caribbean alone and many would do just fine.

A no-brainer choice would be one of the U.S. Virgin Islands. It is part of the U.S. and picture perfect and mostly pristine on St. Croix and St. John but there are towns. You don’t really have to give up anything if you don’t insist on having a big city nearby or need a huge job market and there are always people coming and going. You can easily travel to the British Virgin Islands (among many other varied islands) as well as San Juan, Puerto Rico for the big city stuff. A U.S. citizen can just move to the USVI as long as you have the money and it isn’t insanely expensive. There just aren’t that many good jobs.

Probably one of the Hawaiian Islands. I like being an American, with all the rights and privileges that go along with citizenship. Also like my modern conveniences, which, so far as I know, are all available there. Given my sudden wealth, I’ll get a cable package that includes all SEC and NFL games, and whatever the best possible internet connection may be…something good enough to let me run multiple computers online at once, and put together the ultimate uber-gamer “war room”.

Ireland’s too big for your criteria, so I’d probably pick one of the Hawaiian islands, too. I’d miss the snow, but one of my two vacations would be over Christmas, anyway, so I could at least get some snow in then, and I think there might be some on some of the mountains, too. Plus the first-world conveniences and English as the primary language, of course.

Really, with the vacations you’re allowing, I can’t see it as “condemned” at all. I mean, after all, that’s more vacation time than I get right now, anyway.

I was waiting for the catch as well but the OP never hinted of one. What is the downside of this supposed to be?

The downside would be, if a billionaire gave you a bunch of money to retire, you might not want to be on an island. If I could live anywhere in the world, with vacations, I’d be back in Switzerland, not on an island.

Bonaire. It’s easy to get to Aruba and Curacao for shopping if you want, but Bonaire itself is peaceful, not overpopulated, not over-touristy, and blessedly flat compared to the Virgin Islands. It has one really great beach, the best beach I’ve ever been on really, and the scuba diving is pretty well unparalleled. Scuba diving is one of my great pleasures in life.

Hawaii. Hell, most of my family have made this deal, without the billionaire, and mostly without the vacations.

That isn’t much of a downside the vast majority of us. There are a whole bunch of islands out there that most people would be happy to choose from. You presented a choice between nirvana and a kick in the nuts for most people. It isn’t that hard a choice.

I hear Switzerland is nice but most people, including me, would select an island if we could pick one that fits especially with your more than generous rules.

Just out of curiosity, did you really think this was a hard dilemma when your wrote it? If so, why? I really am interested even if the reason is just because you love Switzerland that much. I love the U.S. too but the St. Croix in the USVI is like a second home to me so all I have to do is pack a bag and move there which I may when my daughters are older. There are so many islands available that I can’t see that being a problem for most people. I am more interested in why you thought that it might be.

Arnold, buddy…if a billionaire gave me enough money to retire in style, I would cheerfully kiss his ass on live TV during halftime of the Super Bowl. Then me and my Druidess would dance all the way to our limo for the ride to the airport, and smile all the way to our island “prison”.

I gave serious thought to the U.S. Virgin Islands, but the big island of Hawai’i wins. Jaunts to the other islands, but a mini-ranch above Hilo would do just fine.

Some people would be happy to spend ten months a year (less boat trips) on Manhattan Island, I guess.

Alcatraz or Hawaii

Somewhere in the Caribbean. Couldn’t tell you specifically. One of the rim islands, though. Jamaica, Hispanola and such are too much trouble. I’d want an island that KNOWS it relies on the good will of expats and tourists and will cater to them with a minimum of revolutionary fervor.

The USVI are a good idea but I think for a jefe like I’d want to be somewhere outside the borders would make a better idea. I didn’t spend five years studying latin american history not to pick up a few things.

Zealand.
Location Baltic Sea
Coordinates 55°30′N 11°45′E / 55.5°N 11.75°E / 55.5; 11.75
Area 7,031 km2 (2,714.7 sq mi)
96th largest island in the world. It has Copenhagen, and smaller cities towns and countryside. I can go to Amsterdam, British Isles, Iceland and many Scandanavian Islands.

I count Amsterdam as an island because the canal district, like Venice is a series of Islands. As long as I do not leave the canal district, it fits the need of it being an island.

What? I am not int roasting and sweating. I’m a snow bunny.

I live on an island in SE Alaska, it’s not paradise but i enjoy it. It is about a tenth of your size limit and I only get a month of vacation.

Being “condemned” would mean I could quit my job and see my family twice as much. :dubious:

I’d move about 150 miles south to live on Sanibel Island. For my boat trips, I’d go to Captiva Island, Upper Captiva Island and Pine Island. Beautiful beaches*, great fishing and a couple of old girl friends. I would have picked Beautiful Island right smack in the river by Fort Myers but there aren’t any islands worth visiting within the specified distance.

*Excluding Pine Island, but there are some nice mud flats there.

It’s a bit small, but the island in the middle of the lake at Kinkakuji in Kyoto would suit my tastes nicely, although Zealand is mighty tempting too.

Singapore

Probably not Pitcairn, although I’d love to visit it during one of those month long vacations!