I pre-populate the locations via Google Maps and TripIt. Major items like airports, hotels, appointments go in first. I usually add a few locations while at my hotel and not distracted by traffic.
Online Maps:
1) Log into Google Maps on desktop. Star my locations.
2) Log into Google Maps on iOS/Android. Stars appear
Offline Maps:
1) Create a Map in Google Maps.
2) Add locations and routing as needed
3) Export
http://www.igismap.com/create-save-e...le-google-map/
4) Convert to whichever file format needed (usually kml2gpx
http://kml2gpx.com/)
5) Import to offline map app like OSMAnd, MapsWithMe (Android) or Pocket Earth (iOS).