24. Taking Woodstock (2009)
Director: Ang Lee
Stars: Demetri Martin, Imelda Staunton, Henry Goodman, Liev Schreiber, Jonathan Groff, Eugene Levy, Emile Hirsch, Paul Dano
Vacation destination: Woodstock, NY
There are few things more appealing than the vacation situation thrust upon Elliot (Martin) who inadvertently plays a pivotal role in the infamous Woodstock Festival of 1969 when he offers up a permit and his family's hotel to the organizers of the festival.
In return, he gets the summer trip of a lifetime: taking LSD with two strangers in a van and watching Woodstock's massive crowd swell while under the influence. Or, as his van-mate would say, "Tiny little people on stage with their waves of tiny electric voices." And, thanks to the psychotropic waves of color, we're also transported to a new place, the closest thing we'll have to a groovy vacation while remaining on our couches.