Hebrew as it's spoken today in Israel, or ancient Hebrew? There's a lot of intelligibility between the two, but it's mostly in the written form. In ancient Judea you'd be more likely to find a speaker of dialect that'd entirely dead today.

As far as English goes, obviously you wouldn't find any English speakers in ancient Britain, but you could find Saxons that spoke a language that English is descended from. There won't be much intelligibility, if any at all, but I wouldn't be surprised if it was equally unintelligible as ancient spoken Hebrew.