From New York, I will be traveling alone to the following cities:

-Delhi
-Jaipur
-Agra
-Varanasi
-Mumbai
-Himalayas

Questions:

(1) Can I do this itinerary without a guided tour, or is this just too much to do alone?

(2) How do I travel between cities in India? By train? By plane? By bus?
When I visit multiple cities in Europe, I book train tickets online with Eurorail, and it's simple. Is it different in India?

(3) If visiting all these cities by myself for the first time would be logistically overwhelming, can you recommend a group tour that is inexpensive?

(4) Where is the best place to visit in the Himalayas? I'd like to get a good view of these mountains, and perhaps do some hiking for a couple of days, but nothing too serious.

(5) Should I fly from New York to Delhi, or New York to Mumbai?

(6) Finally, when are the best months of the year to visit the places I mentioned?

FYI: I will be in India for about 2 weeks.

i think you have packed in too much for 2 weeks....

you can rent a car & driver for delhi, jaipur & agra....the rest of the places you would have to fly to....

there are travel agencies that can help you hire a tour guide....i would not go with a group....

not too familiar with the himalayas....i would suggest a place like nainital which would be a 5 hour drive from delhi....

mumbai is the odd one out in your list of cities....there are other places you could visit unless you really want to go there....

oct, nov, feb, & march for all the places except the himalayas....

like i said before, too little time....i would either drop mumbai or the himalayas....

Why not? Is it because you then have to conform to where they want to take the group, and not cater to my individual needs?

Wouldn't I be missing something if I skipped Mumbai? It would be like taking a tour of the U.S. and skipping New York.
What would you suggest for my itinerary? What places would you include for a comprehensive (for 2 weeks) tour of India?
Funny, I've been told that March starts getting too humid and warm. I would love to go in March, as this would give me some time to prepare and do my homework.

pretty much....i know a bunch of people who went for the guided tours & they all said that they would have done so differently if they had the chance again....

i really would not compare mumbai to new york....more like chicago....its a good city (i lived there for a bit) but a tour to the states without chicago won't be missing much....

there are so many more places you can see as compared to mumbai....places like udaipur & jodhpur in rajasthan would have more touristic value than mumbai....you could keep mumbai as the starting or end point of your journey so that you can spend a day or 2 there....but once again, you wouldn't be missing much if you didn't....

march does start to get warm but its still good weather....the best time in my opinion would be all of november or mid feb - mid march....

The Himalayas are a diverse region that spans a wide breadth of north and east India. It would really take it's own 2 week trip to appreciate it from either the north or the east perspective (rather different experiences IMHO). If it is your first time to India, I would recommend staying Inland and not venturing too quickly into the thinner air before you've gotten settled in. Also, I would not recommend any Himalaya trip by yourself. At the very least, you should travel as part of a group w/ an experienced guide, but ideally you would bring your own group

Well, I just want to get a brief highlight of one of the Himalayan areas. I'm not looking to see the whole mountain range, as it is gigantic.
I've heard the name "Himachal Pradesh" thrown around a lot. What do you think? Would this fit in with my itinerary, and how representative of the Himalayas is this area?

I think of Bollywood like seeing Broadway in New York, but since you've actually lived there, I think you would know about this more than I would.
Also, I've read much about the "energy" and "life" that exists in Mumbai which "must be experienced". This kind of seduced me to want to go there.
I'm going to look more into Udaipur & Jodhpur. Thanks.

Well, this is good news, then, as I was originally planning on going in Jan, thinking this was the most ideal time. It's nice to not have to rush to make this imminent deadline. I'll now probably go, either in late Feb to early Mar, or next November.

good call....jan is a terrible time to visit north india....

I would avoid Mumbai like the plague. The Delhi airport is far superior to get in the country/connect.

Also I agree Mumbai is nothing like New York. It is very dirty and a vast majority of the population lives in slums (tents with tin roofs) As you approach Mumbai airport and if you look out of the window, you will see some buildings spread out and the rest of the area between buildings are occupied by the tents with tin roof.

The Himalayas are great and would definitely recommend that. Maybe you can visit Shimla in Himachal Pradesh.

So, there's really nothing to see in Mumbai? What about Bollywood?
Your advice about flying into Delhi being far better than flying into Mumbai is well taken. I will definitely avoid it.
It's funny how an analogy comes into my head. When traveling to Italy, Rome Fiumicino (Delhi) is way preferable to Milano Malpensa (Mumbai).
I have heard of Shimla in Himachal Pradesh mentioned before. Is this a standard destination for many tourists heading for the Himalayas?

My personal preference is Nainital which is in Uttarkhand.

that's what i suggested in my earlier post....its much better than shimla....

If you are feeling more adventurous, you could go to Sikkim or even Leh, though it is at a pretty high altitude and will be extremely cold in the winter.

India is too large with disprate climates in different parts of the country that it's impossible give one ideal time of the year.
Two weeks is too short a time to cover the list, unless you are on touch and go schedule.
You will have to be more specific with Himalayas, as these mountains stretch from the north to the east, over nearly 2000 miles.
I doubt that one travel agent can help with all of these places.

Be especially careful about sunburn in the mountains. The only place I have been sunburnt in India was in the mountains. What do want from the mountains? A relaxed time away from the plains and the crowds, breathtaking views, adventure? The choice will depend on what you want from the mountains.