What city/must-see would you pick when headed south of Thailand?
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Hua Hin and Prachuap Khiri Khan. Ao Manao in Prachuap is one of the best beaches in Thailand. Also a couple of mountain top temples over looking the town and beach. Take the Ordinary train from HH to Prahuap which runs down the coast.
Check out Koh Lanta ?
Ao nang koh lanta
Chumpon Province. There are some beach and some Island that you can visit.
I think that if you only have a couple of days, Khao Sok National Park is a good possibility. It is beautiful, relaxed, and really is worth your trip and not gonna be a “same same but different” kind of situation.