Darjeeling is an old hill station that still runs on its two original draws — tea and the view of Kanchenjunga. Add the narrow-gauge toy train, a Tibetan-influenced food scene and easy add-ons like Kalimpong and Pelling, and it makes a comfortable five-day trip for a group.
The Kanchenjunga sunrise from Tiger Hill means a 3.30 am start and a shared jeep queue, and on a cloudy morning you will see nothing at all. It is still worth doing, but keep a second morning in hand — October and November give the clearest skies of the year.
Happy Valley is the closest estate to town and runs short tours through the factory. The toy train joyride between Darjeeling and Ghum takes about two hours and should be booked ahead in season. Ghum Monastery, the Batasia Loop and the Himalayan Mountaineering Institute fill the rest of the day comfortably.
Kalimpong is two hours away and quieter; Pelling in Sikkim, with its own Kanchenjunga view, is a common four-day extension but needs an Inner Line Permit for Indian nationals travelling to some parts of Sikkim. Groups usually fly into Bagdogra and take one booked vehicle up.