re = /\bto\b(?:(?!\bto\b).)*?CITY\d+/
str = 'John from beautiful CITY1 in sdfsf to dsfs in sf to abc CITY2 to CITY3 for 3 days'
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