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On one of my characters, the guy in the wagon at Whiterun will take me to almost any city in Skyrim.

On my slightly newer character, he only lets me go to four cities - Markarth, Riften, Solitude and Windhelm.

My first character has all those plus places like Morthal, Winterhold, and Falkreath.

What's the reason behind this? It's not based on which cities I've visited (as I've only visited Riften out of the four on my second character).

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This is speculation, but perhaps it's affected by your main quest progress, the civil war, or bandits along the travel routes that you've killed. – Arkive Nov 28 '11 at 16:25

Locations only show up if you have enough gold to travel to them, it is likely that your newer character did not have sufficiant gold to travel along the more expensive routes.

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False. After handing over my entire fortune to Lydia and traveling to a stable, the driver offered me the entire usual list of destinations. :-) – Ben Blank Nov 27 '11 at 18:29
I have around 800 gold on me, so I don't think that this can be the case. As well, the prices are usually some at 50g and some at 20g, and all the ones listed were priced at 50g, there were none of the cheaper ones. – victoriah Nov 27 '11 at 21:38

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