Hello. Since tsuave of the PS3Trophies.com website posted the trophy guides for Tales of Monkey Island (all five chapters), I just thought that I would post the trophy guides for the same game so as to save them from disappearing or being completely buried in a barrage of other trophy guides. Here's a guide for ToMI Chapter 1, and I hope this thread can be stickied. (WARNING: SPOILERS AHEAD!)
Leave Well Enough Alone: Experienced a brief, yet horrifying transformation.
In the jungle, whilst you wander aimlessly, you'll come across a wishing well. Go up to it and press [Cross]. You'll transform into the mightiest pirate in all the land! ...and the trophy will unlock.
The Sounds of Science: Heard De Singe treating four different patients.
1. When you first arrive on Flotsam, go to De Singe's house near the Screaming Narwhal and knock on the door.
2. After a bar fight at Club 41, knock on the door at De Singe's house again.
3. After knocking Winslow off the Narwhal, knock on the door on De Singe's house again.
4. Finally, after helping D'Oro out, return to Flotsam and knock on the door on De Singe's house once more.
Why Is My Older Brother Laughing?: Encountered a shipload of references to the previous Monkey Island games.
This can be very, extremely tricky, so make sure you examine everything at the very beginning of the game, up until you meet the Voodoo Lady. Here are some tips from another PS3 Trophy Guide site that "shall remain unnamed *cough* .org *cough*, paraphrased as so not to incriminate the innocent"-
1. Examine the Hatch, Quarters Door, and Wheel on Guybrush's ship.
2. Complete all conversation with LeChuck, in particular his history as a ghost and the monkey's secret.
3. Examine the Jail on Flotsam Island.
4. Examine all items and conversation options with the Voodoo Lady.
Is That a Pox on Your Face, or Are You Just Angry to See Me?: Experienced the effects of the pox on the charming inhabitants of Flotsam.
Once you return to Flotsam from the Voodoo Lady's shack the first time you meet her, go see Crimpdigit and ask him how his business is. Then go back to the Screaming Narwhal and fire the cannon. It'll destroy his precious unicorns. Now go knock on his door and he'll flip out a bit. Now, go one screen right and talk to Hemlock McGee. Through the course of the conversation, he flips out too. Go back to Crimpdigit and ask how business is. He'll flip again. Go back to Hemlock and keep asking different options until he flips a second time. Then go back to Crimpdigit. This time, show him the Unbreakable Bottle and he'll bring out the Unbreakable Bottle Breaker. Return to the Screaming Narwhal and fire the cannon again. Return to Crimpdigit's house and take the Unbreakable Bottle Breaker, then return to Hemlock and talk to him until he flips out for his third (and final) time. Go back to Crimpdigit again, ask him how business is again, and he'll lament about the loss of his Unbreakable Bottle Breaker then flip for his third, and final, time.
Bats Right, Throws Lame: Repeatedly threw things...kinda.
Return to Flotsam after getting the Young Miss Mini-Bombs from the Jungle. Repeatedly throw mini-bombs at Winslow, both lit and unlit, prior to knocking him off the ship. Later on, after a scene when De Singe closes the door of the Ancient Portal in the jungle (assuming that you have a Pyrite Parrot), and after you used the Unbreakable Bottle Breaker on the crystal nose of the door face, toss the Pyrite Parrot at the topside of the Ancient Portal.
LeChuck Slayer: Defeated LeChuck (again).
Use the Cutlass of Kaflu on LeChuck after finishing the recipe and dipping it in root grog.
Use the Source: Met Deep Gut.
After accomplishing all three tasks for Nipperkin, head for the Voodoo Lady's shack and tell her the password: "Deadline".
This Ain't a Library: Intensely browsed a prominent bookshelf.
Also done while accomplishing things for the "Why Is My Older Brother Laughing?" bronze trophy. Look at the Voodoo Lady's bookshelf and she will warn Guybrush. Despite the warning, look at the bookshelf up to five times, and Guybrush will lose his voice over the coughing and wheezing. Keep looking up the titles in the bookshelf until a book title repeats twice, indicating that you've read the whole rack of books.
The Legend of LeFlay: Quizzed everyone about Morgan LeFlay.
The first time you land on Flotsam, take the flier of Morgan LeFlay that you see here, and show it to the proper people in order: Reginald Van Winslow, Gaffer Crimpdigit, Davey Nipperkin, Joaquin D'Oro, the Voodoo Lady, and finally Hemlock McGee.
The Winds of Freedom Blow: Escaped from Flotsam Island.
Once you've finished rearranging the final wind idol, which happens to be a messed-up idol, and escaped with Winslow on the Narwhal, the trophy unlocks.
Many Unhappy Returns: Found Elaine.
Once you've managed to entrap your hand in the tar and ordered Winslow to set sail for the Rock of Gelato, the final trophy unlocks at the very end of the chapter.
I'll do more guides for the remaining chapters later when I get a chance. ;)