What's the obsession people have with trying to see everything even when they have such a short period of time? Slow down and take it easier, stick to one place or two at most (preferably somewhere close to Bangkok, i.e. Pattaya, Kanchanaburi, Hua Hin). Believe it or not you'll get more out of the trip if you stay put than if you're travelling around all the time.
Arriving in Bangkok jetlagged and on a different time zone is not pleasant. You'll be disorientated, suffering from the heat and humidity, probably exhausted and your body clock all over the place. The first night you'll be lucky if you've got the energy to do anything let alone party then fly to Phuket the next day. I wouldn't recommend anyone visit Phuket anyway, over priced tourist trap full of scams.
Ayutthaya is a few hours from BKK, it takes a good day to see all the temples, then you'll have to go back to BKK. That will be an exhausting day. Better to go there when you can stay the night. This won't be possible if you have to fly home this day.
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Should cover everything.... minus Chiang Mai.
Doesn't even begin to scratch the surface actually. Stick to Bangkok and Pattaya if the beach is a must. Personally I'd forget about the beach and do BKK and Kanchanaburi, beautiful place, lots of history (WW2), nearbye waterfalls, elephant treks, rafting, tiger temples and so on. Some nightlife too, few gap year and backpacker tour companies stay for a few days here so if you get your timing right you can smash some drunken Scandanavian chicks. I know a bar owner there and she's always got them in the bar, playing drinking games, stripping off etc.
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Why wouldnt I be able to bang some non pros in Bangkok?
Most people who go to Bangkok only fuck pros. There are basically 3 types of girls in Thailand. The pros / semi pros / bar girls / massage girls who sleep with men for money or view you as a walking ATM, the middle class to HiSo girls who for the most part wouldn't be seen dead with a filthy farang because it would lower THEIR status and then the girls in the middle who might consider dating / sleeping with a farang but only if you don't act like a total sex tourist and none of their friends find out.
It's not a difficult place to fuck your brains out with non pros but you need time, you need to pipeline the internet, you need to appear to be staying in the city for a good length of time, you need to know where to go. One night stands from clubs is not that common in Thailand, unless the girl plans to ask you for money in the morning. Chances are if you're planning on staying in Sukhumvit to be 'close to the nightlife' you're not going to be visiting any clubs where any decent Thai girls go. Most Sukhumvit clubs are touristy places filled with sex tourists and working girls. Even if you do venture further afield and go to a Thai club there's a high chance none of them will show you any interest anyway.
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Will be looking for basic, cheap, clean accommodations near the nightlife.
How much will that run me?
Define basic and cheap? What's your budget? or some people basic and cheap is a $5 room (some of them are OK if you just wanted a place to crash) for others basic and cheap might be $50-$100. I usually opt for somewhere around the $20-$25 a night mark and I'm happy with that, others might think it wasn't nice enough.
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Not sure if it's still open but Spicy was a good after hours and also used to transfer to a smaller club across the street above a restaurant about 8am.
Fairly sure it's still open and Swing across the road probably is too. Be warned OP it's a total whore house of a club. Really is a last resort place when you just want to continue drinking and partying all night or don't care that you're probably going to end up going home with a pro.
And I agree with what someone else said, take your own condoms. Thai ones are too small and break easily, even the Durex.