You can stack the deck in your favor to win at Caravan virtually every time. A Caravan deck has a minimum of 30 cards -- which you can buy from merchants or find on dead bodies -- so you need to choose those that will get you between 22 and 26 consistently while also giving you defensive cards to use against your opponent.

Here's a great setup. Take these cards with you:

10s
9s
8s
7s
6s
Kings
Jacks
Aces
2 Jokers

Jacks, Aces and Jokers are defensive plays. Use Jacks to remove cards from your opponent. Ace and Joker played will remove all cards of your Ace's suit (an Ace of Spades and Joker will remove all spades from the table). Kings will double whatever they are placed on. Optimally, 6+K+K = 24.

Here's how to play to win: To open, lay down your highest or lowest cards first to start the 'base' of your caravan. 10+9+8=27 so don't use this combination. 6+7+8=21 so don't use this either (unless you put your Ace down after the 8 to make 22). But every play between is a winner. As stated above, 6+K+K=24 is also a winner. Using this strategy, you are virtually guaranteed to win each hand of caravan, no matter how high your luck!

You can accumulate nearly unlimited items and caps by playing Caravan. Seek out vendors with lots of cash and items. Buy all the items you can afford off them, then challenge them to a few games of Caravan and win back all your money!