For Hive posts, you can only pin at one location, but on the mobile Haveyoubeenhere here app you can pin multiple locations (waypoints) and connect them together to make a post, like this below.
You can then cross post from the app to Hive and Pinmapple will take the first waypoint and pin that on the map. Hopefully that helps, but if you still have any further questions, feel free jump onto our discord (the invite link is on the Travel Digest), @Martibis will be the best person to help you