Hi, Belinda!
Great clarification; thanks so much!
For your 5 p.m. reservation at Chef Mickey's (yum!) I would make
The Pirates League reservation for 3 p.m. While you'll be ready very early, you'll want to have fun with post-pirate transformation pics, many of which can be taken at great photo ops in and around Adventureland.
Once the transformation and photos are finished, it will take 5-10 minutes to head out of the park gates and another 10 minutes to swashbuckle over to Disney's Contemporary Resort (again, either walk or take the monorail. Just allow for a bit more time if you take a monorail as you may need to wait a tiny bit for the next one to arrive.) There are some neat shops at the Contemporary as well as some pressed penny machines near the escalator to the monorail; these can occupy some time if you are early for your dinner reservation. Of course, the arcade can take up some time as well, but even if you arrive as early as 4:30, I would simply check in at the restaurant. You might be able to be seated early if you arrive much earlier than your reservation, but the extra time will alleviate your worries if The Pirates League is running behind or if an unexpected pit-stop is needed.
Have a wonderful trip and happy planning, Belinda! Please send more questions as you think of them, too. I love to help!