Bermuda or The Caymans? 

Which will it be if Bernie Sanders becomes president? I’m running, fast, that’s all I know. He was on CNN’s State of the Union this morning. I heard little tidbits like Community Policing, estate tax changes (and not for the good), raising income taxes…..I’m the Gone Girl (well, not THAT Gone Girl if you read the book or saw the movie!)

Pros: I can ride bikes everywhere, wear Bermuda shorts, order lots of Dark n’Stormy drinks, it’s easy to get to, and it’s where I can buy the best Royall Bay Rum aftershave for Mr. EOS.

Cons: Weather is iffy. Numerous direct hits by named hurricanes. Houses are very very very expensive but if I’m saving on my tax load by hiding money, hey, I guess I can afford a nice house. I could do this one, with some decorating updates. A mere $14.9

Cayman Islands
Pros: The beaches. The weather. The beaches. The weather. The beaches the weather.


Who is joining me? Maybe I can get Catherine’s British husband to forego Wyoming for his own flag on Bermuda and get us some native perks of becoming residents. John, c’mon. 🙂

21 thoughts on “Bermuda or The Caymans? 

  1. If it were the Bermuda I remember, I’d be there in a heartbeat. It’s not. Airfares are woefully high. Coral Beach isn’t the same. Trimingham’s is gone. An always expensive island, it seems to lack the civility we once were happy ( or, almost happy) to pay for. I can count 20+ visits to Bermuda, the last being about 10 years ago. As a non-Bermudian, you are limited in what properties are available for purchase. Mega Bucks help.
    The good news is that you can buy Royall products in the US. Goslings Black Seal is available. I just bought 1.75 liters of it. After trying out a bunch of ginger beers, my favorite for dark & stormy’s is Regatta. But, you may enjoy the trials as much as I did….
    No idea about the Cayman’s. I thought they were just for off-shore deals. But, what do I know.
    Consider Australia. Yes, it’s a hike but so what.

    1. I’ve only been to Bermuda a couple of times, first when I was about 16 and my hipster aunt took me and barely supervised my comings and goings. We stayed at the Pink Palace. We had a blast.
      I have cousins who go to Bermuda once a year to play golf and also say the place has changed. The MidOcean club was classic. Does it even exist anymore?

      If I lived alone and didn’t want a thing to do with my family, I’d already BE in Australia. Alas…… 🙂

  2. Mid Ocean is still a private club but nonmembers can get tee times albeit at hefty greens fees. It is in Tucker’s Town which is a gorgeous and exclusive area of the island. For a golfing trip, it doesn’t get much better.
    We’d go for squash tournaments and quick getaways. We don’t play golf- yet.

  3. If you’re not in the water diving multiple times a week, I’d say no contest in BDA’s favor. I really didn’t find Grand Cayman that nice of a place. No real character, no areas with a neighborhood feel and not a lot to do other than dive.

    1. My REAL first choice is to move to Barbados. But I’m not sure they have any tax advantages. Agree about the Caymans lack of character but again, if I’m hording my money there safely away from more Progressive doctrines of ruination, I can save enough to live half the year in Barbados and the other half lowering my standards in the Caymans.

      1. I’ll defer to a true tax professional reader, but I think the only way you get any US tax benefit from moving to Barbados is by renouncing your US citizenship like Bill & Hilary Clinton’s pal Denise Rich. Otherwise, Uncle Sam taxes US citizen income worldwide no matter where you live and I believe the same is true for the estate tax.

        1. Yes, I sadly know that. Just thinking ahead, fearful of what the next eight years might bring us, fiscally and otherwise with another Prog leading us down the road to destruction. I love America too much to leave but I sure would love to have more than $1.50 to leave to the kids and with all the Dem high tax laws they want to enact, I might as well just toll over now.

  4. Here’s a publication we’ve been receiving for quite some time although I seldom bother to read it. Mr S likes to dream of exotic- and economical- places to live.The July 2015 issue has an article on taxes for expats.

    I’m not sure if you have to actually live in the Caymans or just leave your money there and stop by once a year or so.

  5. Best of all worlds, domiciled in Grand Cayman, zero taxes, with a condo or 3-6 months time share((very common)), AND a house in Bermuda. Bermuda is little more than one hour from NYC. Closer than Bridgeport!

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