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I suspect that things must generally happen in sequence or things you saw in the video don't happen.
Check that you have done all these things:
- Go into bar (west side).
- Talk to Wild Rick.
- Get spoiled wine from basement. Give it to Rick.
- Take Rick's money bag. Leave bar.
- Outside the bar, talk to Jack... who is happy to get the money.
- Go east to Jack's ship.
- Put 4 large cannonballs on 4 targets on ship.
- Talk to red-bearded pirate on beach.
- Drag rum barrel from ship to target.
- Target appears in front of cannon. Put cannonball on it.
- Shoot cannon / destroy statue.
- Pirate who was blocking lower deck comes up... now out of the way.
- Go to lower deck. Talk to the friar.
- Chase the monkey to the room at the top that has two hammocks.
- Go back to the friar, who then moves.
- Enter the room. Get metal key.
- Go back to house with pirate flags. Get the two keys in the upper left corner.
- Go to small house in the south. Look through telescope. Remember placement of the red X that you see.
- Go to small house in the north. Look through telescope. Remember placement of 2 red X's.
- Go out. Put 3 stones where you saw red X's in the telescopes.
- If stones are correct, the gold key will appear.
- Take gold key to big house with pirate flags.
- Get doll out of Jack's room.