The Letters of Paul

First:   Dates from the Crucifixion to Death of Peter and Paul

33: Crucifixion of Jesus (Finegan, section 620)
36: Conversion of Paul (Acts 9:1-30), 14 years before the Jerusalem conference (Gal 2:1)
38: Paul visits Jerusalem, three years after his conversion (Gal 1:18)
38-47:  Paul evangelizes in Syria and Cilicia (Gal 1:21), and other regions. 
47-48: Paul's first missionary journey. (Acts 13-14)
49 Early Jerusalem conference (Acts 15:1-29, Gal 2:2-10)
49 Spring, - Fall 49: First half of Second Missionary Journey.  (Acts 15:30-17:34)
49-50 Winter, - Early Summer, 51: Paul stays in Corinth for a year and a half. (Acts 18:1-11).
51 Early Summer,:  Paul is brought before Proconsul Gallio (Acts 18:12-18:17)  This is the primary fixed point in Paul's life, because it's the date having evidence on when it happened.  Because of a plaque with the date of Gallio's proconsulate, and we know the proconsuls had one year terms. 
51 Late Summer and Fall, :  Second half of Second Missionary Journey (Acts 18:18-21)
51-52 Winter, Paul winters in Antioch. (Acts 18:22-23)
52 Spring, Beginning of Third Missionary Journey. (Acts 18:23-19:1)
52 Summer - Fall, 54: Paul spends two years and three months in the Ephesus (Acts 19) 
54 Fall, - Spring 55: Completes 3rd Missionary Journey: arrives in Jerusalem (Acts 20-21)
55 Summer-Summer, 57: Paul was arrested in Jerusalem (Acts 21:33) and jailed in Caesarea (Acts 23:33), under governor Felix.  After two years, Felix was succeeded by Porcius Festus.
57 Summer-Fall 57: Paul stands before Festus and King Agrippa II, and appeals  to Caesar (Acts 24-26) He would be tried in Rome instead of Caesarea. Paul is sent to Rome by ship. They were ship-wrecked on Malta.  (Acts 27)
57-58 Winter spent on Malta (Acts 28:1-10).
58 Winter-Winter 60: Paul completes the journey to Rome.  He stays there under house arrest, for two years (Acts 28:11-30) so the record in Acts ends. Guesses as to the next dates
60-67 According to Eusebius, Paul was released in A.D. 60, and continued his missionary work.    We know that he had planned to go to Spain (Rom 15:24,28).  There are references by Clement of Rome, and the Muratorian Fragment (late 1st to 2nd century sources), that Paul did make this trip.  Paul's letters to Timothy and Titus, indicate that he made it back to Greece after visiting Spain.  It is impossible to prove that this Spanish trip happened.
67 He was martyred with Peter under Nero, on June 29th, A.D. 67 

Dating the Letters

Paul did not write any extant letters until the beginning of his second missionary journey in A.D. 49.  The oldest letter is 1 Thessalonians, and it was written around 49-51.  He continued writing letters up until his death in 67, so we have a range of 49-67 for all of his letters. 
Some letters can be dated precisely, such as 1 Thessalonians,
1 Thessalonians A.D. 49 Dating based on 1Thess. and Acts.
Galatians A.D. 49-54 Dating based on when Paul visited Galatia (Gal 1:6-9). 
2 Thessalonians A.D. 52 It was written after 1Thess. and before Paul's visit to Macedonia in 54.
1 Corinthians A.D. 52 Written from Ephesus.
Romans A.D. 53 Dating based on cross references with 1 Cor. and Acts.
2 Corinthians A.D. 53 Written after 1 Corinthians,
Philippians A.D. 58-60 One of the four captivity epistles (Phil 1:7,13,16)
Colossians A.D. 58-60 One of the four captivity epistles (Col 4:18)
Philemon A.D. 58-60 One of the four captivity epistles (Phlm 9)
Ephesians A.D. 58-60 One of the four captivity epistles (Eph 4:1) 
1 Timothy A.D. 65.
Titus A.D. 65 Same as for 1 Timothy.
2 Timothy A.D. 67. Paul says he is about to be martyred.