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Hitchhiking out of Dubrovnik - which is the last major town in the south of Croatia - does not seem that difficult, although it might require quite some luck. Just climb up to the costline road and hitchhike on the E65 to the South.  Most drivers, though, are heading mainly towards either [[plane|airport]] or the small town of [[Gruda]]. It is still about 10 km from there to the [[Montenegro-Croatian bordercrossing]] between [[Herceg-Novi]] (Montenegro) near Gruda (Croatia). Since the traffic is pretty low on that road, - particulary in the late afternoon/evening - you will need some luck to find someone crossing the border and willing to take you. Most probably you will be picked up by some tourists. If you wait considerably long, you will probably need to walk to the border.