Realistic? Definitely. I'm starting my first tour this Thursday morning. If I can do it anyone can so get planning.
Every last drop of advice you'll ever need is covered in this forum (admittedly it takes a while to find it all), the Travelling Two book and site and general tinterweb.
Dunno about prevailing wind direction. I have a 20 mile loop I like to ride regularly but every time I do it, I somehow have a headwind on both the outbound and return journeys. Go figure.
Do not accustom yourself to use big words for little matters.
A man who uses a great many words to express his meaning is like a bad marksman who instead of aiming a single stone at an object takes up a handful and throws at it in hopes he may hit.