Wow... I just spent an hour long writing an e-mail complete with numerous links, just to watch ENWorld not recognize me, tell me to log in again, and cause me to lose everything. Which is bulls...
Theroc, your character is good to go. Voadam, we have yet to fill all PC slots.
Anyway, I'll type more later. We'll start in Damascus in 1386, which is a run down and once great city due to suffering from an overthrow of its ruling dynasty and the Black Plague a generation before. Oh... and it has 14 more years to go before getting smashed by the Mongols, so the atmosphere will definitely be tense. I'm using wikipedia for a lot of my info, but here is another link I found and recovered for the actual Canterbury Tales:
The Canterbury Tales
Do a wiki search for the years 1385 and 1386 for events in the Middle East and Europe. The Mongols are coming in from the east, and there is unrest due to Ottoman invasions and political infighting in central Europe. The western Crusaders were kicked out of the Middle East, but there is still significant trade and interaction between the cultures going on. Also, pagan faiths are still commonplace, but often kept somewhat secret despite the power of Christianity and Islam at the time.
The caravan leader plans to travel from Damascus, then towards the ruins of Antioch as he trades from town to town. Just west of Antioch, he will charter a large ship or several smaller ones to take the caravan into the Black Sea and into Romania (Transylvania and Moldavia). Then through Hungary, the Holy Roman Empire, northern France, England, and finally to his home in Canterbury.
The Caravan will have few horses, so it consists mostly of pedestrians, wagons, and mules moving at a fairly slow pace. The caravan master, Alfred Fayweather, has taken this route three times now for much profit as he brings spices from Persia and India, then trades these for dates, brass and tin from Damascus and the surrounding area, then trades these along the Black Sea for silver before arriving in Hungary and switching these for gems. He then goes into the Holy Roman Empire where he trades some of this for furs and gold. Then its off to France where he picks up some art pieces and sells everything he has collected in England for British pounds and a few political favors.