You can simplify initiative to make sailing combat run more smoothly. The easiest option is to place the ships’ pilots at the top of the initiative order, rolling Sailing Lore for initiative but comparing their results only to one another. This ensures that both ships maneuver into position before anyone else on board takes their actions. The two sides of the conflict need to deal with the same circumstances for their attacks, spells, and other actions.

If a player character is piloting the ship, let them decide how to Drive it and roll normally. The Drive action is built to work well when multitasking, so if the pilot has few things to do, the player might be too strongly tempted to take complicated Drive actions. It’s best to make sure the pilot has other options for the remaining 2 actions during their turn, such as casting spells, making ranged attacks, or commanding NPC sailors.

The PCs might want to have an NPC pilot their ship. If an NPC is piloting a ship during a naval battle and the PCs are primarily fighting, it’s best to assume that the ship is staying on course to allow for combat to take center stage rather than have the pilot make tricky maneuvers. Have the NPC pilot Drive with 1 action; assume they succeed rather than rolling. A PC can spend a single action to give specific orders to the NPC, in which case the NPC typically tries to enact those orders the next time they Drive.

Battles in sailing combat should be kept to a close enough distance to allow for a variety of ranged offensives between ships. It’s much harder to get melee attacks in the mix, so if your party is heavily melee-focused, it might be better to skip sailing combat and stick to the other types of naval conflicts. Alternatively, you can make sure they have options to get to the other ship, such as separate rowboats or teleportation.

Some of the attack options include:

• Ranged Weapon Attacks: Creatures can attack with their normal ranged weapons and use any appropriate feats, magic item abilities, and the like.
• Ranged Spells: Spells with a range can also be used normally, and some cones, lines, or emanations might even reach in some situations. You might want to make such spells harder to aim on a moving ship, similarly to the penalties noted in Ranged Attack Challenges.
• Siege Weapon Attacks: The crew can attack using the siege weapons mounted on a ship. This usually takes multiple rounds, the effort of multiple crew members, or both.
• Ramming: One ship can ram another using the Run Over action. This is very dangerous for the pilot and their own vehicle and is a last resort for most captains.

The Vehicles in Combat rules note that attacks made while on a vehicle that has moved within the last round take a –2 penalty, or a –4 penalty if the vehicle is uncontrolled or any action in the last round had the reckless trait.

That section also describes the rules on cover. In sailing combat, creatures on a ship’s top deck don’t get cover against attacks from the other ship’s top deck, though they might be able to find cover behind masts or cargo on the deck. Creatures using hatches on the decks below typically have standard cover and can Take Cover as normal.

If the ships have larger crews, you can easily end up with allied NPC crew members attacking unimportant enemy crew members. To keep the game moving quickly, avoid playing out every single attack roll for these characters. Instead, play these NPC clashes narratively. Thin the numbers as the fight goes on, with the minor characters being defeated or knocked overboard.

If you’re using siege weapons, you can also put NPCs to work Aiming and Loading them. You can place all of the crew who are helping with siege weapons together in initiative so all the maintenance of the siege engines happens at once.

The weather at sea can transform a sailing combat encounter. Including a weather condition is optional! It’s usually best to use only one type of inclement weather and to avoid combining it with other major complications.

Dense Fog or Rain: The normal rules for fog or rain causing concealment matter at fairly large distances. If you want extremely dense fog or rain to affect naval combat, you can create concealment at a much shorter range. Because this adds a further detriment to ranged attacks, dense fog is typically better used in boarding combat.

Winds: Strong Winds have the strongest impact on sailing combat. The default rules should mostly be reserved for flying creatures. Imposing penalties on ranged attacks is less interesting, especially when the penalties for moving vehicles are likely already hurting ranged attack accuracy.

Winds can have a greater and more interesting impact on the movement of ships. At the start of a round, tell the players the direction of any high wind, such as blowing from the northeast, and tell them how many feet it will push all ships at the end of the round (usually 5 or 10). Movement against the wind is difficult terrain, and moving with the wind moves the ship 10 feet (2 squares) each time it would move 5 feet (1 square). At the end of the round, the ships are pushed the amount you stated at the start of the fight. As the new round starts, say whether there are any changes to the wind. Typically, the wind’s direction changes no more than 45º per round, such as going from blowing from the northeast to blowing from the north.

If a ship becomes broken, the fight continues, but if it’s destroyed, the sailing combat is over! The ship will eventually sink, though it takes long enough that you have time for another scene. It might be time to play out a final duel atop the slowly sinking remains!

Crew members can typically swim, surviving the destruction of their ship as long as they get taken aboard another vessel without too much delay or have a large enough piece of flotsam to rest on.