Maybe stay in Bangkok and meet a guy there who can go with you to Chiang Mai and Phuket (be your tour guide). I think you'll find it easier to meet guys in Bangkok than other places.
If you go to Phuket, I don't recommend you take the boat trip to Phi Phi Island. I got violently sea sick as did most of the other people on the boat--but that was during rough rainy season in July.
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