The time of year you go will also influence where you go. Is it monsoon season? Are blizzards likely? If so, you may want to choose a different date or place. The advantage to travelling during the off-season is you will likely deal with fewer crowds.
Photo Gallery Timing For Your Travel Destination
Timing For Your Travel Destination Images
Research the local festivals and holidays. In some countries, everything closes for a month in August for the Summer work break, which might make it hard for you to shop.
Other countries have strict fasting laws for religious holidays, which will make dining out a challenge. Know the weather, festivities, and customs of your travel destination before you decide.