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A possibility, which is ok for sending large attachments with emails, but I cannot comment on how the Kindle side would manage:
Yahoo mail allows you to send up to around 150MB attachments via Dropbox. You attach the file to your email and if it is over 25MB (I think it is) it asks you to sign into Dropbox (or to create an account there if not already held). Your email goes to the recipient and has a link to the Dropbox file; the recipient does not need a Dropbox account to retrieve it.
If the file is a book, I suspect this won't work direct from Calibre, but easy enough to handle outside of it, but as to whether the Kindle can pick files up from Dropbox I have no idea so is up to you to determine if interested.
Alternatively, if it is a .pdf file you can split it into smaller volumes easy enough and email each volume separately - the same with .epubs but I suspect not so easy with .mobi; but you could convert .mobi book to .epub, split it into smaller volumes and convert each volume back into .mobi volumes.
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