10,000km, 7 months.
It is now possible to go through the border between East Timor and Indonesia making this trip possible. It will, however, require a visa extension as Indonesia only grants visas for 60 days to Canadians. Visa extensions are for 30 days. With 4400 km to do in Indonesia 90 days should be more than adequate.
This can be considered in two legs:
- East Timor to Bangkok: 5795km 4 months
- East Timor 208 km
- Indonesia Border to Denpasar ~1000 km
- Denpasar to Belawan 3418 km
- Malaysia to Bangkok 1169 km
- The weather constraint for this leg is that the Malaysian peninsula should be done in Jan-Feb to avoid monsoons.
- Melbourne to Darwin 4096km 2.5 months
The weather constraint is that crossing from Adelaide to Darwin is best done in the winter: May to September. The prevailing wind, a modest 10kmh, is from the SE.
Optimum Route and Timing
It is probably best to start in Bangkok, Feb 1st, cycle to East Timor. Then fly to Melbourne (Jun 1st) and cycle to Darwin (going this way is best because the wind in the desert would be generally with us). Fly home from Darwin (Aug 15th).