Your first chance to play Caravan is in Goodsprings, the town you start the game in. Go to the bar and talk to Trudy - she'll tell you about Ringo, who's at the gas station. Say you'll go talk to him and you can go into the gas station - one of the dialogue options with him is to play Caravan.
One user has commented that you NEED to talk to Ringo in order to be able to play Caravan EVER. I am unsure whether this is a bug or a constant thing. Either way, just make sure to talk to Ringo before it's too late. Thanks Octobot Super. Ringo is not very good at the game so this is probably the best spot to get the achievement. Depending on your choices during his quest, he will then go to Crimson Caravans (East of Freeside) so you can play with him there too.
Note: You can hit X when deciding how much you're going to bet - set it to 1 cap at first, then there's no risk if you happen to loseCaravan confuses the hell out of me, so here are some basic tips - I managed to get this achievement and I still have no real idea how to play. But if you're smarter than me, you can also read the holotape Ringo gives you - it explains all the rules.
Basically, both you and your opponent have 3 piles - called caravans - of cards. The aim of the game is to getting the total these piles to be between 20 and 27, and to outbid your opponents caravans by having the highest value.
General Info- Numbered cards simply add their value to the pile. To play a numbered card, it needs continue in the same numerical direction - ascending or descending, and/or be the same suit as the previous card. Jokers placed on a numbered card remove all other cards of this value from the table.
- Aces add one to the pile. Jokers placed on an ace remove all other non-face cards of the aces suit from the table.
- Jacks remove the card it's placed on. (Tip - Placing a Jack on a King will also take away the card the King is doubling)
- Kings double whatever card you put them on.
- Queens add no value - instead, they reverse the current direction and the suit of that caravan.
How to Actually Win 3 GamesThe first 3 turns you must start your 3 caravans. Try to put either high or low value cards, since you'll be either ascending or descending. Remember, aim to get the value between 20 and 27.
Also remembers you can put face cards on your opponents caravan. So if an opponent has a caravan with a value between 20 and 27, feel free to to put a King on and it will go over, or put a Jack on the highest value card to put it under.
If you've got a bad hand, you can hit LT to swap out the selected card from your hand. You can also hit RT to remove an entire caravan if you please.
So basically, just remember what face cards do, try to make all your caravans add up to 21-26, and put cards on your opponents side to 'sabotage' them. Since Ringo kinda sucks, it shouldn't be too hard.
After you get this achievement, win 27 more games and you'll get another achievement:
(Also, there's a challenge for losing caravan 5 times, it gives you some XP so when you're done with the achievement you can quickly go for that as well)