Maybe some of these will give you inspiration:
http://moorstation.org/typoasis/pirates/freebooter.htm
Or, have you searched for images of Oates' letter to see what his handwriting looks like?

Maybe Voyage would work for you:
http://www.myfonts.com/fonts/fenotype/voyage/

Voyage looks very much like what i'm looking for! Thank you so much Special-K

A font accurate to the period, but also something that resembles a Diary Entry? Something handwritten.

None of which describes Voyage. Careful—attractive though Voyage is, it is a popular style now that may look dated in a few years.

Here is an item from my grandmother’s autograph book; I believe it is a man’s hand.

A handwriting font like Olicana would be closer to your specification.

Or one of Laura Worthington's script fonts, which have more vigour than Voyage. I would take a look at Azalea.

While the story of Oates' futile sacrifice is moving, I think I'd be more inclined to a quote from Shackleton, who brought all his men home alive: "Superhuman effort isn't worth a damn unless it achieves results."

The quote has two main links to me, one, it is what inspired me to travel (The quote is included in a travel tattoo), and secondly, the story of Captain Oates was told to me by my father, who has designed the tat.

Thanks for all the suggestions guys, i'll take a look at them all and have a think