http://pluto.jhuapl.edu/mission/mission_timeline.php gives the timeline of the New Horizons probe currently on its way to Pluto .  
In annex the amazing , but not spectacular , animation of NH voyage trough the solar system from the viewpoint of Pluto , looking down at the sun.  
NH is the white dot in the beginning leaving the planet Earth ( white orbit ) , which gets a gravity assist from Jupiter ( the red dot originally at the left ) .  
One can see NH approach Pluto . For an observer on Pluto there's amazingly no indication the probe is heading towards Pluto until the end of the animation where NH makes a dive under Pluto .
 
Initial conditions were taken from the JPL ephemeris on 01/01/2009 , ie after the gravity assist with Jupiter .  
I think the people of JPL made an incredibly  good precision job because I get a close encounter with Pluto at 14/07/2009 , precise on time at a distance of only 80.000 km , whereas the flight shedule predicts an approach on the same date at 10.000 km .  
So only a small upwards burn may be needed to be right on schedule .  
 
Animation can be downloaded to view on full screen .  

Quote from frankuitaalst on 05/02/09 at 05:59:06:

Assuming that Pluto is a fixed point in your animation, it Looks perfect to me.  You are seeing the non-fixed Earth cause a "wobble" every year as it orbits the Sun.  Have you tried the animation as viewed from the Sun?
 
-- Kevin

Yes , I remember some stories about drunk astronauts , but things get even worser even for spacecraft ..

"Soon" New horizons will meet Pluto .  
 
A big while ago I made the following animation showing New Horizons view on the Plutonian system when it arrivés at Pluto .  
The camera view is only 0.05 ° and stays centered on Pluto .  
Charons orbit is in grey .  
The sim starts about 200 days before close approach and ends about 300 days later .  
 
(I hope New Horizons will give us an lot better view ! )