Having Trouble As A DM

MNblockhead

A Title Much Cooler Than Anything on the Old Site
Lots of great ideas on this thread. I'll focus on specific tools and content that you might find helpful from free to expensive.

First - nice to have a model or battlemap of the ship. It helps build a sense of possession and personality for the ship. On the expensive side is the upcoming Wiz Kids "The Falling Star Sailing Ship" (https://wizkids.com/the-falling-star-sailing-ship/). Or you can get a battlemap that you can print to scale, such as the Galleon in the 0one Crimson Sea PDF set (see below). I used Zero Hour's Sailing Ships battlemap. I just printed them out on cardstock and cut out and put each level on top of the other. If there was action above AND below, I could just place the ship segment battlemaps next to each other. It worked well and is inexpensive: https://www.drivethrurpg.com/product/76432/0-hr-Sailing-Ships. Another excellent battlemap set, is Scrying Eyes Games Ships of Fantasy: Tall Ships series. I bought the Caravel Fleet PDF, which had three Caravel maps and versions with sails furled and of the ship at dock. https://www.drivethrurpg.com/product/111743/Tall-Ships-15-Caravel-Fleet

Next, have a good set of mechanics that give each player a role on the ship. These can act as additional class features while on the ship. Also, different NPCs will have specific jobs and skills that will make them worth protecting and keeping happy. Have rules for moral and ways to upgrade the ship. Some nautical combat specific magic rules, etc. I VERY MUCH prefer Ronny Hart's nautical adventure rules over the recent Unearthed Arcana rules. I highly recommend checking out his Nautical Adventures: A Supplement Providing Ship to Ship Combat Rules, published on his Dungeon Master Assistance blog: https://olddungeonmaster.com/2015/05/05/dd-5e-nautical-adventures/ It provides much more than combat rules. There are discriptions, images, battlemaps, and stats for a variety of era-appropriate ships. Rules for crew costs and moral. Prices for ships and upgrades. Travel rules. A character sheet for the ship and more. This PDF is a must have for nautical adventures in DnD IMO.

0one's Blueprints series has the excellent Crimson Sea "virtual box set". It contains nine Blueprints plus a color map folio. The color map folio contains a color version of the Crimson Sea Map plus a poster map of the Black Leviathan, the Galleon of the pirate lord Karnak. For the 9 blue-prints, they are actually a sett of many maps giving you entire islands and pirate village locations. The "Rule the Dungeon" feature of 0one's PDF maps is pretty cool, allowing you to show and hide layers before printing. The 0one "blueprints" are great for homebrew games. They are just very detailed maps with a key that will give a name for different rooms/locations, but you fill in the descriptions, plot hooks, npcs, etc. Some will give introductory paragraphs with some optional fluff, but they are all about the maps.

If you want a well fleshed out coast and island setting material, check out Frog God Game's Razor Coast setting book and map folio, which they offer in both print and PDF: https://froggodgames.com/frogs/?s=Razor+Coast&post_type=product It is for Pathfinder, but you can easily just use the 5e stats for the same monsters, you would mostly be buying the books for the maps and descriptions/stories.

The 7th Sea game system has a wealth of setting material you could repurpose for a 5e game. Get the old or new PDFs and use them as inspiration for maps and story ideas. https://www.drivethrurpg.com/browse.php?filters=10101_0_0_0_0

John Wick's Ships and Sea Battles (Swashbuckling Adventures), written for d20 system and 7th may give some inspiration. I bought it, but found I didn't use it. Ronny Hart's Nautical Adventures was sufficient for my needs, but check it out: https://www.drivethrurpg.com/product/12492/Ships-and-Sea-Battles-Swashbuckling-Adventures?it=1

Hope this helps!
 

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Thyrwyn

Explorer
I usually let my players tell me who the BBEG will be - meaning that I don’t start with a specific BBEG or even a specific endpoint in mind. I throw out ideas and encounters with groups and organizations that inhabit the world and pay attention to which ones the players/characters react most strongly. Which ones do they start plotting against? Which ones do they start seeking out? Which ones do they enjoy thwarting?

Once they’ve done that, it’s just a matter of narrowing the focus and fleshing out the NPCs they’ve crossed paths with until one really stands out - or until several stand outs get together and form a cabal intent on dealing with “those pesky kids” (the pcs).

That said: pirates are historically a response to a distant, but powerful, authority or authorities. They make an excellent source of enemies for pirate campaigns: who’s been sent to deal with the “pirate problem”? Who’s responsibility should it have been to begin with? How unified are the pirates? Are they freedom fighters? Thieves? Opportunists? Some of each? Is someone or something trying to unify them - and to what end? Who’s trying to keep them divided and why?

Throw some of these ideas out there and see what sticks. Your BBEG should develop naturally from there.
 

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