Lynn,
I could almost write a book in response to your questions, but I don't want to bore you too much! so this will have to do:
First of all I would plan for at least 3 weeks. If you only have 2 weeks I would choose either Southern Thailand or Northern but not both.
Secondly, if you go in October you will be going in low season which means you will benefit from lower prices, less tourists and rainier weather (in the case of the Gulf of Thailand ie. Ko Tao, Ko Samui and Ko Phangan, it will be full-on monsoon. I do not recommend anywhere in the Gulf during this time, Andaman sea side is preferable). Prices jump drastically, especially in the South, approximately Nov 1st.
Thirdly, Phuket is the most touristy place in Thailand and quite frankly if you are looking for something cultural or authentic you will not find it here.
While I don't recommend staying anywhere on Phuket, it can be a good jump off point for some preferable places to visit (From Bangkok you can fly direct to Krabi or Phuket, I actually suggest making Krabi your jump-off point instead of Phuket. It is more authentic and much cheaper). So, you could fly direct from Bangkok to either Krabi or Phuket, stay one night, then take off:
For diving, without a doubt the best in Thailand is the Ko Similian Islands (which are only a short distance from Phuket). If you can arrange a few days in this region, I would do it (you cannot stay in accommodations on the islands but I believe there are some tour groups that do an overnight camp trip). You can stay on the mainland in Khao Lak.
I agree with others who have posted here who have recommended Khao Sok National Park - also very close to Phuket and the Ko Similians. The restaurant the gal is referring to might be Thai Herb - probably the best restaurant in the Khao Sok region. There are no nice beaches here, just awesome scenery, wildlife, and karsts.
For the nice beaches and amazing karst scenery, you could jump on a ferry from either Krabi or Phuket to Ko Phi Phi (also touristy but much nicer than Phuket), Raileh, Ko Lanta (more peaceful), and perhaps even as far south as Turatao (much less touristy).
For the cultural part of your journey I suggest northern Thailand, starting with Chiang Mai (tons of flights up there, no need to book until you get to Thailand). I personally feel that a trip to Thailand isn't complete without venturing somewhere north. The prices are better, the food is the best and the people seem so much friendlier. If you can't make it as far as Chiang Mai (and even if you can), I also suggest a trip to old Sukothai (fabulous place, much less touristy, peaceful and full of amazing ruins).
I have found in my Thailand travels that wherever you are, the best way to really get a feel for the Thai culture is to either jump on a bicycle or scooter and just take off, stop wherever you want and talk to people. I lived there and my best memories are those I had while on the bike and while in the North or Northwest.
Lastly, I wouldn't book anything before I got there....
Good luck!!
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