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As gorgeous as Bermuda is, it is quite North of the real Caribbean, so you should remember that seasons are important depending on what you really want to do on this island paradise.
If its warm weather and beach time you are after, stick to late spring and summer for your Bermuda vacation. Its is at the same latitiude as the Carolina's so you won't be dissapointed with the warmth and beauty at this time of year.
If you are looking for a quiet break where you can enjoy shopping, architecture and history - and maybe a little golfing, you can explore Bermuda in the off season and you won't be dissapointed!