G450 Sunrise HUD (Photo: Jeff Stafford)
Complicated? The actual flying part of international operations is easier today than ever and the rules are becoming more standardized. The hardest part, it seems, is facing the ramp inspector or the tax collector. I can't help you with the tax man but for the inspector you need to have a good SAFA plan.
You should have a library of everything that controls how and where you fly. While web sites (like this one), a knowledgeable friend (like Eddie), the Jeppesen State pages, or even the world's best flight planning service are not enough. This page should get you started.
What follows are quotes from the relevant regulatory documents, links to those I have for download, and links to sources otherwise.
14 CFR 91. 14 CFR 91 pertains to all aircraft.
14 CFR 135. For operations under 14 CFR 135, 135.3(a)(2) specifies that while operating outside of the United States, operators must comply with:
It is imperative for all pilots planning an international flight to become familiar with the appropriate Federal Aviation Regulations (FAR) and the information contained in Notices to Airmen (NOTAM), International Flight Information Manual (IFIM), Aeronautical Information Publication (AIP), International Civil Aviation Organization (ICAO) Annexes, and regulations of the foreign countries over which they intend to fly. [AC 91-70A]
Current and historical FAA advisory circulars are available at: http://www.faa.gov/regulations_policies/advisory_circulars/.
These are hard to find and often cost a lot of money to get. If you spend a lot of time in a particular country, it might be worth the investment if you can get it in a language you understand. Fortunately, the U.S. AIP is free: http://www.faa.gov/air_traffic/publications/atpubs/AIP/aip.pdf.
FAA Orders 8400 and 8900 can be found at: http://fsims.faa.gov/PICResults.aspx?mode=EBookContents.
These are available at http://www.faa.gov/regulations_policies/faa_regulations/.
Finding everything you need from the ICAO can be a challenge, so far the best source out there has been: http://www.bazl.admin.ch/dokumentation/grundlagen/02643/index.html?....
* Not all of Doc 4444 seems to have been reproduced in the 15th edition, so you might need to look at the 15th edition and then then 14th edition for some sections.
The Customs and Border Protection website provides a few helpful documents: http://cbp.gov/xp/cgov/travel/.
Portions of this page can be found in the book International Flight Operations, Part I