Probably Fiji. I’d like to be on one of Australia’s local islands, but the temptation of going back to the mainland would be quite great. Probably.
Having said that, I treasure isolation. Perhaps I’d manage at any location, as long as I had all my creature comforts and small risk of being eaten by monsters.
I’d be on an island in the Pacific Northwest, somewhere where it gets chilly and drizzly and foggy and damp but doesn’t snow very much and people on the nearby islands and the mainland know what good coffee and Internet access is like. You can have your sunburnt sandtraps in the monsoon zones; I’ve got a neater, sweeter setup in a cleaner, greener land.
Amen!
Can I decorate my island? Full blown coastal fortress FTW!
I currently live on a big island, bigger than Iceland or Cuba. Your deal would still be an awesome trade-up for me. No job, better weather, more vacations, MORE time off-island, and frankly, better island.
I call Whidbey Island! It’s mine you curs!
In an odd coincidence someone at work asked what place on the earth’s surface is opposite Sydney. It’s some spot off the coast of North Africa in the North Atlantic. And the nearest land is the Archipelago of the Azores and we all want to go vist there now.
One of the cayes of Belize.
Long Island, New York.
Does the Isle of Dogs count as an island? If so, I wouldn’t mind living there, though it would be frustrating to not be able to visit the mainland.
Iona, off the coast of Scotland. It’s tiny, and peaceful. I could also nip over onto Mull for some awesome fish and chips every so often.
I’m not as big a fan of sunshine as most of you, clearly 
Not saying it’s my final choice, but Martha’s Vineyard or Nantucket would be on the list – beautiful in the summer, I don’t mind the cold in the winter, and plenty of culture/food/shopping in season at least. Then you get some peace and quiet all winter.
(For that matter, do you count Cape Cod as an island, since there is a canal separating it from the mainland?)
Kauai, paradise on earth.
Hey… if you had this guys email address you’d tell me right? I’m seeing absolutely zero downside to this deal.
Dammit, that’s the answer I wanted. You could spend half your time on Staten Island or Long Island if you wanted.
I’d go for Cyprus, myself; big enough that there’s a reasonable amount of stuff to do, and the Turkish-Greek thing seems to be stable and headed (very slowly) towards reconciliation. Plus my parents live there.
Saint Martin/Sint Maarten. We are headed there in a couple of weeks. It is my favorite place on earth. There are several islands within a kayak trips journey (Anguilla, St Barts, etc).
I’ve been to Tahiti, and found Papeete crowded and dirty, though you can get to rural areas within a short drive. Spent a few days on Moorea, that was much better, more rural. The best was Bora Bora, fabulous scenery, very nice people, good food, very relaxing.
You can easily take a ferry to Moorea. We flew to Bora Bora, it was about an hour if I recall.
Here’s a list of islands of the world by area. All the Hawaiian islands are in play, as are all of the Caribbean islands except Hispaniola. Ditto all of the Greek islands in the Aegean.
I’d probably choose a Caribbean island, with an eye to (a) a good selection of nearby islands for variety, (b) English-speaking and American-friendly, and (c) a decent variety of good restaurants.
Maui would be my top non-Caribbean choice, but I figure I could always spend a month in Hawai’i once every couple of years, and still have plenty of mainland time left over.
I guess I’d plan on retiring where I currently live.
You should probably make explicit that islands connected by bridges or tunnels don’t count. So Bainbridge, Mercer, or Whidbey don’t count, but Vashon and the San Juans would. This criteria also keeps out rubbish like Manhattan.
I’d be climbing the walls in days if I was confined to any one place.
Over the years I have been to many “tropical paradises”, and for me at least, the novelty wore off very quickly.
Not born to be a lotus eater I guess.
I’d pick Oahu. I don’t think I’d be happy living longterm outside of the United States. And I’d want at least one decent sized city around.