New timeline based on trilogy
I'm trying to keep things straight, so bear with me and see if there is anything to be added. I'm guessing on ages. Jack may be older than what we previously guessed, but here is my speculation.
Jack is born: According to the POTC visual guide, Jack was born at sea in the middle of a storm.
Jack: 15, Will and Liz are born: Will is born to Bootstrap Bill and mother. He lives in England. Elizabeth Swann is born to Weatherby Swann and mother. Sometime before she is 12, her mother dies.
Jack: Between 18 and 22 (most likely)------ Jack works for the EITC under Beckett. Although not specified in film, it is speculated that Jack freed a shipload of slaves, thus branding him a pirate. According to the POTC Visual Guide, Jack is an average/below average swordsman in spite of being taught by an Italian swordfighter in exchange for gold. He is, however, a fantastic sharpshooter. Somewhere in his life, he obtained all his "effects," including a compass that points to what you want the most from the mysterious Tia Dalma.
Jack: 23, Will and Liz: 8----- Davy Jones makes a deal with Jack to resurrect the Wicked Wench. Jack renames it the Black Pearl and somewhere here appoints Barbossa as first mate. He can captain it for 13 years before he has to serve 100 years of service on the Flying Dutchman.
Jack: 25, Will and Liz: 10-----Barbossa mutinies against Jack, maroons him on an island. Jack suffers intense heat exhaustion and escapes only by help of the rum runners. Will and Liz are, uh, 10.
Jack: 27, Will and Liz: 12--- Will and Liz meet after Barbossa as captain of the Pearl sinks Will's ship. Liz finds him and takes his medallion that Bootstrap sent to him. Jack is probably tracking the Pearl. Norrington is about 19 or 20.
Jack: 35, Will and Liz: 20. Curse of the Black Pearl: Our trio meet, Will learns his father was a pirate who may be alive. Elizabeth gets her first real taste of pirates and learns she can hold her own, and Jack gets the Pearl back, shoots Barbossa dead, and escapes a hanging with the help of his new allies. Will is supposed to be the greatest swordsman in the series. This places Norrington at around 27 or 28.
Jack: 36, Will and Liz: 21. Dead Man's Chest: Will and Liz face death for helping Jack. Jack's 13-year deal with Davy is up and the evil captain of the Dutchman tracks him down. Will meets his dad, contemplates a plan on stopping Jones. Liz becomes a pirate, and with Will as a teacher, masters swords quickly. Jack dies. Norrington steals the heart and gives it to Beckett. He is 28 or 29 at this time.
Jack: 36, Will and Liz: 21. At World's End : Jack escapes the Locker and begins to fear mortality even more than before. Norrington saves Liz and dies probably at 29. Will and Liz grow as pirates, he becoming the captain of the Dutchman and Liz becoming Pirate King. The two conceive a child. Jack explores the Fountain of Youth.
Jack: 46, Will and Liz: 31------- Will and Liz have a boy and Will returns from his sea duty. T&T say that the curse is over, although it raises the quesiton of who the captain of the Dutchman is after Will. There is no word where Jack is at this point in time.