How to plan a mid range trip part one flights and destination The biggest word to understand when planning a mid range trip is flexibility whether that be flexibility with dates or flexibility with destination The goal is to try and find the cheapest flight that you can get to the destination you want to go to MY husband and I created a giant list of countries we would love to travel to at any point These are countries that excite us for one reason or another Once we decide on a date range the larger the date range the better we then look at the list of countries and figure out where would be a good to go during that time period After we narrow where we should go based on weather things to do etc we start looking for flights I use DialyDrop which is a paid service