For getting to Jaco, about the only time that might be troublesome is a Friday afternoon especially if it is a holiday weekend. Coming back from Jaco, Sunday afternoons can get you in a lot of traffic as well as ANY weekday, if you come back through Escazu on 27 later than 3-4pm, you will get stuck in the toll booth/merge/red light problem. I always cut off and go by the airport during times like that. Buzzfla (post above) probably got caught up in that then in rush hour.
That being said, there is constant road construction on 27 and wrecks are frequent. I've sat as long as 3 hours on the side of the road waiting for a fatality accident to be cleared. You just never know for sure how long it might take. Of course, coming back into San Jose rush hour can also hurt...advise guys to not be on the roads around San Jose between 6-9am then 4-7pm as those are the worst rush hour times.
If you really want to avoid traffic, like I do, try to do most of your transfers at night. The road traffic dies after around 10pm and driving then is a breeze.
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