re = /(?m)(?<=^info)(?:\r?\n){2}:(?:\r?\n){2}/mi
str = 'info
:
I went to Paris
xxx
yyy
zzz
info
:
I went to Italy
aaa
bbb
ccc
'
subst = ' : '
result = str.gsub(re, subst)
# Print the result of the substitution
puts result
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for Ruby, please visit: http://ruby-doc.org/core-2.2.0/Regexp.html