I'm pretty sure trains don't go up to Dharamsala (I could be wrong) because of its position in the Himalayas. I think a better bet would be to catch a train to Delhi, then you can get a bus up to McLeod Ganj, it takes about 12 hours - you'll be able to book a bus through most guest houses once you're in Delhi, (spend a night or two in the Pahar Ganj area where there are loads of guest houses and other travellers) so it shouldn't be a problem.
Don't worry about the trains in India! It can take a little while to get your head round it but don't panic - the Indians just have their particular way of doing things and it doesn't always seem clear. Not sure about the Day 1 Day 2 thing, but possibly it's to do with the fact that the train will be starting somewhere and travelling over a couple of days through lots of places, and then on to a final destination, and most passengers will only be on the train for part of the journey, so more than one passenger will be booking the same seat or bunk for different parts of the journey. Dont' worry about it now anyway! It's probably best to wait till you're there to start booking stuff unless you're on a tight schedule and need to book journeys before you leave. Most of the time guest houses in India will book trains for you which takes the hassle out of it - you don't need to be staying in one, a lot have their own travel desk and will sort it out for you if you drop in - if you look in Lonely Planet they'll tell you the guest houses near to where you are and the ones with travel agencies there - where are you flying into? Probably Mumbai? Can you spend the first night or two in a guest house before going to the orphanage? If so, see if you can get your travel sorted then. If not, do it from Pune, which isn't so far from where you'll be.
If you book trains yourself, go to the train station booking office. Often trains have a quota of tickets reserved for tourists, so say you're a tourist. Generally you go to one window to enquire about times and days of trains. The person will look it up for you and tell you the number of the train (or trains) you need. You get a form to fill out where you put this number, the date you want to travel, where you're going to, your name, what class you want to travel in, then go back to the window to book the train. The people working at train stations always have enough English to help you, so don't worry!
Buses are always a good alternative to trains - you can book 'tourist' buses which are more comfortable than local buses and still cheap, so probably you can get a bus to Ellora Caves from where you'll be, if there are difficulties with trains. Again, you can do this through guest houses or travel agencies. You'll really see when you get there that India is very travel-friendly, - unless you're really off the beaten track, places are overrun with guest houses, travel agents etc - and other travellers! so you'll find it much easier than you think to get around, I promise. I didn't plan anything in advance before I went to India, and I was fine - you will be too.
Cost of things in India is very cheap - I haven't heard of a Wachovia card! Most cities and large towns, and tourist towns have ATMS which take visa and mastercard and delta and switch. If not, you'll be able to get cash through money changers, via your credit card - where there aren't ATMs, there are money changers, if you're in places that are touristed.
General costs - a litre of bottled water is about 10 rs, things like shampoo and shower gel and toothpaste are normally 30 - 100rs depending on where you are (prices always go up where there are lots of tourists). Rickshaw rides vary and are dependent on haggling, but a short hop should only be 20 -30 rs; from train or bus stations to guest houses, expect to pay anything from 40-100rs to a rickshaw driver. To have a rickshaw driver for a day might be 200rs or a bit more. Generally I found 500rs a day was fine, more than enough, and a bit extra in case of anything. I normally had 2 or 3000 rs in cash at any one time, which was plenty to keep me going over days where I was in places that didn't have atms. Generally it's good not to take too much out in one go, as you'll often get it in large notes (large by Indian standards anyway) - it's good to have as low denominations as possible, as a lot of shops, rickshaw drivers won't have a lot of change, and even a 100rs note sometimes can be difficult to change, if you're paying for something that's only 10rs. I generally used my large notes topping up my SIM card, where they always have change!
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