When planning a multi-city trip, consider flying 'open-jaw,' which means flying into one city and out of another. This can save significant travel time. For trips longer than two weeks, it's generally recommended to travel slower to avoid exhaustion. Instead of just listing cities, consider exploring a specific region and including smaller villages, beaches, or mountains in your route. You can use custom codes (e.g., #+A for Activity, #+R for Restaurant) to link information between different tabs of your itinerary template, allowing details to auto-populate. Make one of your last days an 'exploring day' to revisit shops, walk around a different area, or go to the beach, allowing for flexibility.