Due to the GameSpy shutdown, the 100% for this game is no longer possible.
+ Estimated trophy difficulty: 4/10 (Trophy Difficulty Rating)
+ Offline: 8 (1, 1 , 6)
+ Online: 2 (1, 1)
+ Approximate time to 100%: 10-20 hours (Estimated Time to 100%)
+ Minimum number of playthroughs needed: 1
+ Missable trophies: None
+ Glitched trophies: None
+ Cheats: No cheats
Age of Booty has a pretty good mix of trophies. There are a couple of easy trophies, difficult trophies, and grinding online trophies. You'll first want to get "Cartographer" out of the way. It's pretty easy and you can take care of it as soon as you download the trophy patch. Work on the challenges next. There are 21 in all, and you have to beat all 21 if you want the "King's Pardon" trophy. While you're going through the easy challenges, also try to get "Bombs Away", "Flushed Away", "Cherry Picker" and "Boom Boom". Each challenge in a difficulty gets harder as you go from one to seven, so get those miscellaneous trophies out of the way as soon as you can. The Hard challenges are where you're going to spend the most time, especially the final challenge. Here is a link directly to chucknorris078's post that helped me out a great deal. I think it's a sure fire method to get through the last Hard challenge: LINK
After the challenges are finished, start grinding out the online wins. You have options and different ways you can go about getting these trophies. The online methods are detailed in the description for "Sea Legs". The online grind is pretty lengthy so be prepared to do them in two, three or more shifts.
[PST would like to thank olsen77 for this Road Map]