It is best to first reach either Shillong(60 km) or Guwahati(150 km) and then start for Cherrapunji. Shillong airport is the closest. Taxis from Shillong are easily available. If you plan to go by train, the Guwahati station is the closest. Helicopter services are available from Guwahati to Shillong - a thrilling experience in itself. Bus service is quite active and good between Shillong and Cherrapunji.
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The most ideal way to visit the sites in Cherrapunjee is to hire a cab.