Northern Thailand is where the backpacker classics still work. The night train remains one of the great budget journeys in Asia, Chiang Mai's old town still smells of incense and fried garlic, and the mountain road to Pai still has exactly 762 curves, a number the minivan drivers treat as a challenge. Here is the route we would do again tomorrow.
Bangkok, briefly, and Ayutthaya
Give Bangkok two or three nights, enough for the Grand Palace early, a canal boat on the Thonburi side, and one proper night market feed. Then break the journey north at Ayutthaya, 90 minutes and under 100 baht by train. The old Siamese capital is a plain of brick prangs and headless Buddhas, best covered by rented bicycle for 50 baht; the famous Buddha head wrapped in fig-tree roots at Wat Mahathat earns its fame. That evening, board the sleeper. The second-class air-con sleeper to Chiang Mai costs around 900 to 1,100 baht, and there is a specific pleasure in the attendant folding your seat into a curtained berth with crisp sheets while the train rocks through the dark.
Chiang Mai
You wake to jungle hills and pull into Chiang Mai around breakfast. Base yourself inside or just east of the moated old city; dorms run 250 to 450 baht, and khao soi, the crispy-noodle coconut curry the north is built on, is 60 to 80 baht a bowl at places like the khao soi alley near Wat Fa Ham. Spend a day temple-drifting from Wat Phra Singh to Wat Chedi Luang, ride a songthaew up the mountain to Doi Suthep for 40 baht each way, and if you do one paid activity in Thailand, make it a full-day visit to an ethical elephant sanctuary in the Mae Taeng valley, around 1,700 to 2,500 baht; walk with the animals, never ride. The Sunday Walking Street market swallows an entire evening pleasantly.
The 762 curves to Pai
Minivans leave Chiang Mai's Arcade terminal hourly for Pai, about three hours and 200 to 250 baht. Take a motion sickness tablet; the road over the mountains is legendarily winding and the drivers are legendarily unbothered. Pai itself is a valley town that long ago decided its job was to be pleasant: cheap bamboo bungalows from 300 baht, a walking street of pancake stalls and live music, hot springs, and the white Buddha climb for sunset over rice paddies. Rent a scooter, 150 to 200 baht a day, only if you already know how to ride one; Pai's clinics do brisk business bandaging optimists. Pai Canyon at sunrise, before the crowds and heat, is the version worth having.
On to Mae Hong Son
Most travellers boomerang back to Chiang Mai; continuing deeper is where the loop earns its name. Minivans wind on from Pai to Mae Hong Son in about two and a half hours, over passes where the jungle steams after rain. Mae Hong Son is the quiet provincial capital pressed against the Myanmar border, its lake reflecting the white-and-gold Burmese-style chedis of Wat Chong Kham in the evening. Guesthouses run 300 to 500 baht, the morning market does a superb bowl of noodles, and the Su Tong Pae bamboo bridge over the paddies just out of town sees monks cross at dawn. From here you can fly back to Chiang Mai in 40 minutes or bus the long southern half of the loop via Mae Sariang.
Timing and budget
November to February is the season: dry, cool nights, clear ridgelines. March and April bring the burning season haze, genuinely worth avoiding. Overall the north runs 1,000 to 1,400 baht a day, roughly 30 to 40 US dollars, less if you settle into Pai for a while, which people have been accidentally doing for decades.