Traveling from Bangkok via train takes more than 12 hours, so it's best to do it while you're sleeping. We took an overnight sleeper car from Bangkok, leaving at 6 p.m. and arriving at 8 a.m. the next morning. We booked second-class sleeper berths with A/C at 690 baht for the top and 780 for the bottom. Since we were leaving in the early evening, we were offered a dinner menu. For 200 baht, we got soup, rice, cashew chicken and broccoli beef for two people, plus pineapple for dessert. The food was cafeteria-fare but worse (too rubbery, too bland, etc.), so I suggest you take snacks along and save your money for Chiang Mai.

You can also reach the city by bus from Bangkok, leaving from the Northern (Moh Chit) bus terminal. Highway travel is considerably cheaper than rail (300 baht for second class with A/C), but everyone we met recommended train because you can sleep through the long ride and don't have to endure winding, bumpy roads.

Have extra cash to burn? You can fly into Chiang Mai for a reasonable price. Bangkok Airways flies from Bangkok to Chiang Mai International Airport daily for 2200 baht. Chiang Mai International is small but comes equipped with a post office and car-rental booth.

Questions?
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