Citationjet (C525/C526) - CJ I / II / III / IV
Flight Crew Air Transport Pilot (ATP); Flight Crew Flight Instructor; Flight Crew Instrument; Flight Crew Multiengine
Flight Crew Last 90 Days 75; Flight Crew Total 4000; Flight Crew Type 1500
Communication Breakdown; Confusion; Time Pressure
ATC Issue All Types; Deviation - Track / Heading All Types; Deviation / Discrepancy - Procedural Clearance
Air Traffic Control Issued Advisory / Alert; Air Traffic Control Issued New Clearance; Flight Crew Became Reoriented; Flight Crew Returned To Clearance
Human Factors; Procedure
We were picking up our clearance from ground control at FDK; for our flight. The clearance we received was 'radar vectors direct to LRP... T295 PRNCE V483 FLIPS.' There were a few difficulties with the clearance. The first one being; our FMS would not recognize 'PRNCE' as being on T295 and the second one was 'FLIPS' was spelled wrong in the clearance and should have been 'FILPS.' After solving these challenges; Tower cleared us for take-off runway 23 and turn direct 'Winchester' [Westminster]. I have not spent much time flying in this area of the country and assume 'Winchester' was the first fix on our clearance 'LRP.' After take-off we made a right turn toward the first fix entered into the FMS. At this time I was starting to think something doesn't sound right. I don't think LRP is 'Winchester.' We then where turned over to departure control. They asked why we turned right. I replied 'because of the military airspace.' Departure said 'do you mean the ARSA' I replied 'yes.' Departure said 'don't do that again.' We were temporarily confused by why they didn't want us turning right; since it was roughly the same degrees of turn either direction. This confirmed that something wasn't quite right so I proceeded to try and verify the identifier for 'Winchester.' Before I was able to look it up; Departure ask 'are you turning direct to Winchester' so; I asked for a vector. Departure said 'turn to heading 130.' I then found the identifier for Winchester (IME) [EMI] and we proceeded to navigate to it.  Soon after this; Departure cleared us to another fix; not on our clearance (I do not recall the fix). I told departure the fix was not on our clearance. There was some more communication between us and departure then suggested they had a different routing for us then the clearance we received. All of the above events happened at a very rapid rate; allowing for little time to formulate solutions.Lessons learned:1. Consider including the name of the first fix in your take-off brief.2. If in doubt ask ATC.3. Don't hesitate to ask for vectors while you figure things out.4. Consider asking what direction tower wants you to turn; if there is any doubt.
A CE525 Captain departing FDK reports a track deviation when PCT clears him direct to 'Winchester'; which is not familiar but assumed to be the first fix of the clearance. It was not the first fix of the clearance.