The following are some tips and rules for running a gambling session. Gambling can be fun and found in a variety of formats in campaign worlds. This article provides quick tips and four detailed options to get you started running games of chance for your players. You’ll find a mix of info for running games in casinos, taverns, and back alleys. You’ll also notice that these games have a nautical theme, but this can easily be changed.

Quick Tips for Running Gambling

  • Encourage other PCs who are not gambling to get involved with side bets, watching for cheaters, or anything else they come up with. Spellcasters can really help increase the odds for a PC who is gambling. What happens if someone gets caught cheating or casting a spell?
  • How fair are the games? Is the deck stacked against the players? Does the house refuse to pay out big winnings?
  • Decide ahead of time if gambling is something that is legal and held in casinos, highly illegal and punishable, or something in between.
  • Try to keep a balance between being too simple (flipping a coin, rolling a d20) and too complex.
  • Sometimes the best rules are to have no rules and to use ability checks and attack rolls.
    • An ability check (such as Sleight of Hand, Insight) can work well for general gambling.
    • For PCs that are actually proficient with gaming sets, now is your chance to run that epic chess game, poker game, or dice rolling in a back alley.
    • For something like archery or darts just use attack rolls. Add in a bracket with rounds if you want to run a tournament.
    • Blackjack can be run by rolling 2d10, with 1s able to represent a 1 or 11.
    • For a Poker-like game see Sloops & Sailors below or grab some poker dice.
  • Slot machines can be a fun way to show that the city you are visiting has some advanced mechanical devices. A 3d6 roll requiring 3 matching numbers would be a simple take on a slot machine.

Example Games

Captain’s Wheel

This casino game features a large ship’s wheel with twenty spokes sitting horizontal on a table. Each of the spokes are numbered one to twenty and colored black (odd) or white (even). The table around the wheel provides places for six gamblers to sit.

To wager on Captain’s Wheel a player chooses one of the following betting options based on where they believe the wheel will stop:

  • A number between 1 and 20.
  • Black (odd) or white (even).
  • Low (1 to 10) or high (11 to 20).

A croupier (or dealer) accepts wagers from the six gamblers and appoints one of them to be the captain who spin the wheel (rolling a d20). The captain position generally rotates through each of the six gamblers. The wheel is spun and whichever spoke that the spin settles on is the winning number and color. Fortana’s Wheel pays out as follows:

  • A player who chose the correct number wins twenty times their bet.
  • A player who chose the correct color gets their money back plus an equal amount.
  • A player who chose high or low correctly gets their money back plus an equal amount.

Sea Horse Racing

This is a game only found in finest casinos where four giant sea horses race around a massive pool with seating surrounding it. Change this to horses, griffons, fairy dragons, or whatever fits your world.

Each of the sea horse racers is controlled by a jockey. Gamblers bet on which seahorse will win a race to complete a circuit around the 250 yard pool.

Complete the following before each race begins:

  • Provide a name and number for each racer such as Swiftcurrent, Seacookie, Blue Beauty, Boxer, Okeano’s Choice, Stormwind, Fish Bait, Swift, Seacretariot, or any name you come up with.
  • Assign a payout for each of the four racers. Assign 2:1 for the favorite. Roll a 1d10 for the remaining racers to find their payout, where rolling a 5 would be 5:1 payout.
  • Order the racers by their payouts and provide the list to your players who wish to gamble. Explain that a seahorse with lower odds is more likely to win but will return less money on a bet.

A race around the pool generally takes around a minute to complete. To run the race you will need to roll 1d4 and add it to the left odds number for each sea horse four times. For a racer with 3:1 odds, you would roll 1d4+3 each round. After each round describe who is winning and losing. After four rounds, the sea horse with the lowest roll total will end up the winner.

To determine the payout for each winner simply pay anyone who picked the winning racer the amount you set for that sea horse’s odds. On a bet of 10 gp for a sea horse with 3:1 odds, the player would receive 30gp. If you are familiar with horse racing, you can provide your players with greater betting options such as place, show, or even box bets.


This dice game is popular in both the back alleys of port cities and at the casino. This simple game is played with dice made of bone, with the side with a single pip (or dot) representing the skull. The goal of the game is to roll as many skulls (or ones) as you can in three chances.

To make a wager on a game of skulls, a player places a wager, usually set by a croupier (or dealer). The player rolls three dice (rolling 3d6). Skulls pays out as follows:

  • if one skull is rolled the player gets their money back plus an equal amount
  • if two skulls are rolled they get their money back plus double the amount
  • if three skulls are rolled their money back plus triple the amount
  • if no skulls are rolled, the house keeps the wager

Wagers at the casino tend to be much larger, with gamblers far less likely to end up dead for rolling triple skulls.

Sloops & Sailors

The nautical themed sloops (type of ship) and sailors can be changed to anything that fits your world. In Vodari, this is a popular card game played most often for drinks or small wagers in taverns by a group of two to six. Hands are dealt out to players until the groups tires of the game or most of them run out of money to bet.

The goal of the game is to get the highest five card hand, with cards ranging from Ace (1) to 10. Here is a list of the hands ordered highest to lowest:

  • Five of a Kind. Five cards of the same number.
  • Four of a Kind. All four cards of the same number.
  • Sloop. Three of a kind with a pair.
  • Sailors. Five cards in a sequence.
  • Three of a Kind. Three cards of the same number.
  • Two Pair. Two different pairs.
  • Pair. Two cards of the same number.
  • High Card. When a player hasn’t made any of the hands above, the highest card plays.

Each round of involves the following:

  • Each player throws a set ante into the pot.
  • Each player is dealt two cards facedown by a player assigned as dealer for that round. Each player secretly rolls 2d10 and covers their roll with their character sheet.
  • The player to the left of the dealer can choose to add additional coins to the pot or fold their hand and drop out for that round. Each additional player to the left can do the same, ending with the dealer.
  • The dealer then places three cards faceup in the middle of the table. The dealer rolls 3d10 and places the dice in the center of the table.
  • Each player is given the chance to raise the previous bet, match the previous bet, or fold.
  • Once all the bets are placed, the players reveal their dice, with the highest hand winning. In the case of a tie, each player rolls 1d10 to represent drawing a card, with the highest card winning.

The winner of the hand collects the total from the pot and a new round can begin, shifting the dealer to the left.

Equipment Ideas

Looking to outfit your cheaters with some gear? Check out these two gaming set options:

Dice Set, Loaded (5 gp). These weighted dice are well made and provide you with advantage on checks made for rolling these dice. A successful DC 15 Intelligence (Investigation) check will reveal that these dice are weighted.

Playing Card Set, Marked (5 gp). These cards have been expertly bent, colored, or scratched to allow you to know what’s on the front of the card by viewing the mark on the back. A successful DC 15 Intelligence (Investigation) check will reveal that these cards are marked.