This achievement requires the player cross the entire length of the gameplay map. Blackwater is located in the extreme north-east corner of the gameplay map, in the Great Plains region of the West Elizabeth territory. Conversely, Escalera is located in the extreme south-west corner of the map, in the Punta Orgullo region of the Nuevo Paraiso territory.
Notably, this must be completed in a public Free Roam session. Obstacles could include antagonistic players or posses, so it is vital to ensure the cooperation of all players within the session. Playing in a public Friendly Free Roam session is recommended to reduce the issue of attacks from other players.
Sunrise = 6AM, Sunset = 6PM
Go to Blackwater, go to the map and place a waypoint at Escalera. Wait until at least 6AM to leave (leave no later than noon). Then just follow the trail, or for a straighter route, take the very first railroad bridge to Mexico.
Death has no impact on completing this trophy.
Occasionally the trophy may not register if waiting at Blackwater until 6AM and then leaving for the trip. Re-entering Blackwater after 6AM and then leaving should work.
It will take approximately 3-6 hours in game time (~8 actual minutes).
It helps if the player is high in rank where faster horses are available.
There is a bug/glitch for this achievement: if players who are in Blackwater join a posse and transport to a leader in Escalera, when arriving will earn the achievement/trophy.
This achievement can't be completed in a private free roam session.