Way back in 2006/2007 I worked a severely boring, soul draining desk job. I cruised Wikipedia deeply and often. On one of these online excursions, I came across the article for St Helena -- by some measure the most remote inhabited island at the time -- and read more. I learned about the RMS St Helena and how it was the only regular way to get to and from the island. I knew at some point in my life I had to make the journey by sea and check it out for myself.
In grad school I also became acutely obsessed with the (poorly documented) voyage of Edmond Halley to the island in order to observe a transit of Venus. I spent hours in the British Library/Kew looking for anything that might mention what he got up to during that time (apparently the British Governor was replaced for sketchy reasons, etc etc).
A decade later, I got the news that the long-awaited airport was complete and would open in 2016, and that the RMS would be decommissioned. I was in a weird position between jobs and fortunate enough to have the means to book the travel for what was supposed to be the penultimate voyage of the RMS. I had grand visions of interviewing people about what they thought of the airport opening and such (some of which I conducted and wrote about [1]).
The passage I took was 5 days by sea from Cape Town to St Helena, with 10 days on the island. After that, the voyage continued north (which was unusual) to the UK, stopping at Ascension Island en route. That leg of the trip was 14 days at sea.
So really, it was kind of a daydream that turned into a real dream that turned into a lived experience. Wouldn't trade it for anything.
[1] http://www.homoridiculus.com/blowout-on-the-island-of-furiou...