Unbound is definitely the beginning quest, in that I think it refers to you being unbound from your execution and are therefore freed.
The Way of the Voice is the quest where you learn about dragon shouts and your heritage.
Diplomatic Immunity probably has something to do with your status as a prisoner.
Dragonslayer could be one of two things: The final quest where you defeat Alduin, or a parallel quest where you slay dragons and reach a certain point. Either way, the 50 G points to this being a massive achievement. After reading the rest of the achievements, this is likely the ending of the main quest.
Take Up Arms, Blood Oath and Glory of the Dead are related to the Companions, with the latter being the final quest for that faction.
Gatekeeper, Revealing the Unseen and The Eye of Magnus are related to the College of Winterhold, with the latter being the final quest for that faction.
Taking Care of Business, Darkness Returns and One with the Shadows is related to the Thieves Guild. The end outcome being that the Thieves Guild is returned to its former glory... (wasn't this done before?)
With Friends Like These..., Bound Until Death and Hail Sithis are related to the Dark Brotherhood. Mmmm, can't wait for these!
The next three is a BIG spoiler... so...
Spoiler
Taking Sides, War Hero and Hero of Skyrim relate to the civil war. In each case, you side with either the Stormcloaks or Imperial Army and end up capturing important forts and eventually the opposing faction's stronghold city (which is Solitude for the Imperial Army and Windhelm for the Stormcloaks)
The rest of the achievements are miscellaneous stuff. One detail gleaned from this is that you have a separate bounty in each of the nine holds. You can get married, buy a house, get thrown in jail, break out of jail, pickpocket, pick locks, steal things, kill people, yadda yadda yadda.
An achievement called "Oblivion Walker" is gained for finding 15 Daedric Artifacts. There are 17 Daedric Princes. Two are missing, or this is just a roundabout number. It's also possible that the quest for Hermaeus Mora is the same as it was for Oblivion, and this achievement is gained before starting his quest. But I think the two most likely missing parties are Jyggalag and Mehrunes Dagon. Could be wrong though.