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Overwhelmed - 1st timer planning a trip to Asia - need help

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Hi,
I've been reading about Thailand (forums, books, tour companies) and I must admit it's a bit like drinking from a firehose. :) I'm rather overwhelmed with all the information. Initially, I was set on this tour: http://www.gate1travel.com/southeast-asia/thailand-tours-13dclathtu14.aspx but with single supplement, it's almost double. Still affordable overall, but why pay double to be solo? The more I read, the more I want to see, but time and money are restricting my wanderlust. So I'm hoping you good people can help me out a little (or a lot). :)
I have roughly 2 weeks (14 days, but can probably spend a couple more, depending on how things go) and I'd like to spend some of those days on a beach. I am planning to travel in November of this year (or later, but depends on pricing).
Looking at that link above, many of the activities and optional excursions appeal to me (but not the elephants). The thing I don't like about it the location of the hotels. I do like the tour guide and how things are organized and pre-planned, and having a guide explain how Thailand "works". I kinda know how Europe "works" so I know what to expect when going there, and started off with guided tours to several countries.
I'm seriously considering doing something like this on my own, but don't want to shlep luggage and depend on "public" transportation.
I guess, to start, here are some things about me: traveling solo, female, mid-30s, not a partier, LOVE photography (photography tours are waaaaay too expensive), architecture, cultural activities, and somewhat of a foodie (but can't handle spicy food or pork). I like things a little off the beaten path, but since I'm solo and don't want to drive, not toally off the beaten path. Oh, I've traveled some in Europe (Portugal, Spain, England, Scotland, Prague, VIenna, Budapest), and it took me about 5 years of ever-increasing solo days around an organized tour to do a completely solo tour.
I'd love to hire a private guide, if possible. I was also thinking of taking a cooking class.

What can you recommend, based on the above? Any help is greatly apprecaited. Sorry if this is a little all over.

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