Downtime Activities

I'm going to use the Downtime Activities rules found on Xanathar's Guide to Everything starting on page 195.

• Carousing will help you bond with the crew - you must spend some money and time to build relationships with the crew. Most crew members see you as neutral parties at this point. But you can carouse and help move that dial toward friendly. Charisma will be the big help for this item, and you could even annoy crewmembers if things go badly.
• Gambling could earn you coin. Dice and card games occur often onboard - you spend some money and time to make the money you bet. Complications could create debt and enemies on board. Slight of Hand, Insight and Deception may all come into play for this downtime activity.
• Relaxing is you on deck working on your tan and enjoying a Mai Tai - You get to lay low, enjoy the cruise and stay out of everyone's way. You can recover from exhaustion or ability score drops. Nothing harmful happens because of your downtime. No skills needed. Enjoy!
• Researching may yield new information about a specific topic including trade routes, historical records, and trading contacts - Money and time is spent digging up information, compiling and distilling it into some valuable insights. Depending on how the research is conducted you may use Investigation, Insight, History, and Persuasion.
• Training will allow you to learn a new tool skill, weapon proficiency, or language - You will need to work with a teacher (and pay them in some way). Time and ability checks will be required based on the skill you wish to learn. Typically this can take up to 10 weeks to learn a new skill, but things may go faster depending on roles and other impacts. The number of weeks needed to complete training is reduced by your Intelligence modifier.
• Keep track of any days you spend toward the skill. Once you hit the 17 day mark, you can roll to see if you obtain the skill. Then you can roll again 17 days after that, and so on until 70 days pass. DC decreases with each time you roll.