How To Start Dragonborn DLC and Get to Solstheim
Talk about jumping through hoops. Unlike the Fallout series, the Skyrim DLC Dragonborn does not prompt you with a side quest notification in game. You have to either wait to get jumped by a group of cultists or find a specific NPC in the game. Here is a video and step by step guide on finding the Dragonborn DLC trigger NPC in Skyrim.
1. Download it (duh)
2. Make sure you are on or past the Main Quest “The Horn of Jurgen Windcaller."
3. If you installed the DLC while you were playing, you will need to exit out to your Xbox 360 dashboard and reload Skyrim in order for the NPC who triggers the quest to appear in your game. I wasted about an hour after reloading my save from the games main menu before trying that.
4. Once you reload your save, go to the Windhelm Docks. You have to enter the docks through a staircase located on your right after you enter the town. These stairs will lead you down a narrow path. Near the end of the path, there will be another Door that leads out to “Skyrim," exit through that door to get to the docks.
5. You should see a boat helmed by Gjalund Salt Sage, who will take you to Solstheim for 250 gold.
6. If he does not spawn, make sure you have done all of the following and try to wait at the docks during regular shop hours. He may not appear during the late evening or early morning in Skyrim.