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Well Travelled in Dungeons & Dragons 5e

Well Travelled

Overview:
You have traveled all around the world and made friends in every continent. You know so many people that no matter where you go you will likely run into someone. You're the type of person that could go to a tavern in the Underdark and find you're friend from college on the opposite side of the world, or maybe run into an old drinking buddy on a boat. How do you even know these people? Why are you friends with a King from that far-away city? When did you meet that celebrity? It's a long story.
Skill Proficiencies: Persuasion, Perception
Tool Proficiencies: Two types of gaming set, Land Vehicles or Sea Vehicles (If land, Select a horse)
Languages: Two of your choice
Equipment:
1 gaming set of your choice, a backpack, 10 days rations, traveler's clothes, a trinket from a place you visited, a pouch of 10 gold pieces.
Features:
1d8 Specialization
  1. Road Salesman
  2. Travelling Mercenary
  3. Wandering Labourer
  4. Courier
  5. A Sense of adventure or purpose
  6. Didn't belong anywhere
  7. On the run from someone or something
  8. Really are just mad

Feature: Friends around the World

You somehow just know people no matter where you are. You could walk into any bar and always find a table of friends. This comes in handy when you are on the road as often as you are. These friends could help you out with small favours, or might ask help of you. Either way, you'll still be expected to have fun with them, try not to get into too much trouble!

Alternate Feature: Enemies around the World

No matter where you go, you see people you've met before. Probably not a good thing, you've somehow managed to piss off everyone of them. You can't even go into a bar anymore without starting a brawl. You're banned from many establishments and may even be wanted in a few towns. You've gotten pretty good at hiding from people now, sticking to back allies while still moving at a good speed. You can travel through urban areas at any speed while still moving stealth, and can even guide your allies down these secret routes. You also gain proficiency with the disguise kit.

Alternate Feature 2: I Know a Guy

You know many people that can help with anything you could ever want. Need to fix up an old set of armour? You know a good metal worker in the next town over that might give you a discount. Want a new magic item? You know just who to call, but they might want something in return. Many people are still in debt to you for help you've already given them. They might repay you with vital information or free labour: just don't push it.
Suggested Characteristics:
Travelling the road isn't all sunshine and rainbows. You've seen some shit, you've done some shit. But then again, maybe you haven't. How do people know you? Are you the traveler that is always up for a laugh? Or are you still jet-lagged and tire from the trip?
Personality Trait:
1d8 Personality Trait
1 Always tired from the trip
2 Cheery and all smiles
3 Cranky
4 Misses home
5 "I saw so much cool stuff on the way here!"
6 "Reminds me of that one time in..."
7 Longs to get back on the road
8 Forgot to pack everything again
Ideal:
1d4 Ideal
1 Money. I need this money to buy stuff for myself/my family (Good or Evil)
2 Adventure. If you don't know where you are going, any road will get you there (Chaotic)
3 High Places. You always want to have a few friends in high places, just in case (Lawful)
4 Party Animal. There's always a party going on somewhere in the world (Neutral)
Bond:
1d6 Bond
1 I was helped out of a tough spot and want to repay the favour
2 Nothing wrong with a good adventure
3 These are the least-awful travelling companions I've ever had
4 These people are my best friends and I would go anywhere with them
5 This'll make quite the story later
6 I literally have nothing better to do
Flaw:
1d6 Flaw
1 Always rambling on about somewhere they've been
2 Can't sit still
3 Keeps forgetting what language they are supposed to be speaking
4 Just an awful friend
5 Never turns down a challenge
6 A little bit of a hoarder

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