Hey all,

I'm planning a "side quest" for one of my PCs, a morally-ambiguous Paladin, focused on his relationship with his wealthy Blackguard father. I'd like to base a lot of it on the high seas. I'm thinking that his father will host, sponsor or participate in a regatta from Waterdeep to Chult (we're based in Faerun, obviously). When they get to Chult they'll realize the Blackguard father has committed a horrible crime (still figuring that out). 

I'd like the regatta to include meaningful racing mechanics, as well as ship-to-ship combat and swashbuckling. Can anybody recommend adventure modules from which I could borrow relevant content / mechanics? Again, looking for: 

• Ship / yacht racing mechanics (i.e. skills checks, survival checks) 
• Open ocean encounter tables
• Ship-to-ship combat / swashbuckling mechanics

I've found some good stuff on ship travel and management (UA), and a great homebrew on seafaring in general. If anybody can recommend better resources, though, I'm all ears.

Also, recommended adventure modules based in Chult would be cool, too. I've had a lot of luck using / leveraging DMs Guild modules, but could use some guidance on where to start looking.

Thanks much,

Matt

Ghosts of Saltmarsh has some rules that you’ll find useful for water based adventures. You can start there. Tomb of Annihilation is based in Chult so it may be useful to you. 

I'll check out Tomb of Annihilation, thanks!. I can't believe Pendleton Ward contributed! That's so cool. 

Ghost of Saltmarsh has everything you need, from sample ships to rules governing high seas combat. My party is currently off having fun on the high seas and GoS has been invaluable. It includes random encounters for open seas, and if you cross that with the underwater tables from Xanathar's you have all your work done for you.