The journey from Jaisalmer to Kolkata is a massive cross-country trip of over 2000 km. The most practical way is to take a train to Delhi and then a connecting train to Kolkata. Alternatively, you can fly. This route takes you from the desert to the eastern plains of India.
Total Distance: 2050 km driving distance, 1700 km straight-line distance.
Book your train tickets well in advance.
October to March for pleasant weather.