My family has a rule about farang visitors. When somebody’s new boyfriend or somebody’s retired parents fly in, they get the full show — temples, mountains, sea — and nobody goes home needing a second holiday to recover from the first. That rule built this route. I have eaten and sweated through every leg of it, and it is the Thailand itinerary 2 weeks of hoarded annual leave actually deserves: Bangkok, then the north, then the Andaman, with one clever flight stitching it all together. No 4am buses, no six-cities-in-fourteen-days madness. Every mistake in it was made by me, years ago, so you can skip straight to the good part.
The short version: three nights in Bangkok, the 18:40 sleeper train north for four days around Chiang Mai, a two-hour flight down to Krabi for five nights on the Andaman, and one final Bangkok night before you fly home. On a midrange budget, expect around 50,000–70,000 baht per person excluding international flights, and aim for November to March.
The 2 week Thailand itinerary at a glance
Thirteen nights on the ground, one of them rolling through rice country in a bunk. The order matters: cities first, while you still have patience for traffic; islands last, so you fly home with sand in your shoes instead of spending day thirteen upright on a night bus. Prices were checked in August 2026.
| Days | Where | The point |
|---|---|---|
| 1–3 | Bangkok | Temples, canals, an indecent amount of food |
| 4 | Bangkok → Chiang Mai | Last city morning, then the 18:40 sleeper train |
| 5–7 | Chiang Mai | Old city, Doi Suthep, mountain air, khao soi |
| 8 | Chiang Mai → Krabi | The two-hour flight that saves the whole trip |
| 9–12 | Krabi | Railay, Phi Phi, doing nothing on purpose |
| 13 | Krabi → Bangkok | Buffer night, farewell dinner |
| 14 | Fly home | Grief-scrolling your camera roll at the gate |
Days 1–3: Bangkok — the right way to start two weeks in Thailand
First decision: sleep near the BTS Skytrain, because Bangkok traffic is a personality test you will fail. Sukhumvit between Asok and Thong Lo puts you among the best food in the city; Silom gives you Lumpini Park and an easy line to the river; the riverside itself is for anniversaries. Agoda consistently has the sharpest hotel rates in Thailand, so filter for a base within ten minutes’ walk of a BTS station and treat any listing that promises “only twenty minutes by taxi” as fiction. Twenty Bangkok minutes is not a real unit of time.
Day one is temples: the Grand Palace at the 8:30 opening before the coach tours arrive (500 baht, shoulders and knees covered), Wat Pho’s reclining Buddha just south of it, then across the river for Wat Arun at sunset. That first evening, eat wherever the plastic stools are fullest of Thais; the fancy stuff can wait. Day two, get on the water. The Thonburi canals are old Bangkok on stilts — teak houses, monitor lizards, boat noodles — and far easier with someone who knows which piers exist, so book a longtail canal tour or an old-town food walk for the morning, then eat your way down Chinatown’s Yaowarat Road that night. Day three is yours: Chatuchak Market on a weekend, Jim Thompson House if you like silk and a good disappearance mystery, or a pool and absolutely nothing. Our Bangkok province guide has the neighbourhood detail.
Day 4 of your Thailand itinerary: the sleeper train north
Check out, leave your bags with reception, mop up whatever Bangkok you missed, then head to Krung Thep Aphiwat station. Special Express No. 9 leaves at 18:40 and arrives in Chiang Mai at 07:15 — twelve and a half hours, most of them horizontal. The carriages are the newer Chinese-built stock: proper bedding, curtains, plug sockets, toilets that do not require courage. Buy a station picnic first; this is a rolling dinner party and you should cater accordingly.
Book a second-class air-conditioned sleeper — roughly 900–1,050 baht as of August 2026, with lower berths slightly dearer because they are wider and you can sit up in them. The good bunks sell out weeks ahead, so book the day your dates are fixed, either directly with the State Railway of Thailand or by comparing sleeper berths and flights for the same evening on one page. If berths are gone, the one-hour flight is the painless fallback — every option is weighed in our Bangkok to Chiang Mai transport guide.
Days 5–7: Chiang Mai — the slow middle of 14 days in Thailand
You will step onto the platform at 07:15 feeling smug. Good. Drop your bags and go straight for khao soi — curried egg noodles under a crunchy nest of fried ones, the north’s best argument for itself — then take day five gently: the old city is a moated square you can walk end to end, and Wat Chedi Luang’s half-ruined brick spire is the one that stays with you after the trip fades. If your dates land on a Sunday, the walking-street market that swallows Ratchadamnoen Road after dark is the best shopping of the entire fortnight.
Day six, go up the mountain. Wat Phra That Doi Suthep hangs above the city at a thousand-odd metres; entry is 30 baht, shared red songthaews run up for well under 100 baht a seat once they fill, and the 300-odd steps of the naga staircase are the proper way in. Go before nine and you get mist and morning chanting rather than selfie sticks. Day seven, choose your indulgence: a cooking course, a genuinely ethical elephant sanctuary, or the long day out to the White Temple — our Chiang Rai guide covers whether three hours each way is worth it (once, yes). The Chiang Mai province profile has the rest.
Day 8: the one flight that saves a 2 week Thailand itinerary
Here is the itinerary’s only non-negotiable. Overland from Chiang Mai to the Andaman means a full day and night of buses, or a pointless backtrack through Bangkok — a heroic waste of your thirteen nights. Thai AirAsia flies Chiang Mai–Krabi direct in about 1 hour 55 minutes, and as of August 2026 list fares start around 3,100 baht one-way, dropping in promotions. It is the best money this trip spends. Compare times for the Chiang Mai to Krabi flight, take a morning departure, and you trade mountain air at breakfast for warm sea by mid-afternoon.
Days 9–12: Krabi — the island leg of two weeks in Thailand
The Krabi question is Ao Nang or Railay. Ao Nang is the practical resort town: every tour departs from it, restaurants and pharmacies on tap, a proper sunset strip. Railay is a roadless peninsula reached only by longtail boat, limestone walls on every side, and it turns quiet and faintly unreal once the day trippers leave at five. My honest split is two nights on Railay for the drama and three in Ao Nang for the logistics — or all five in Ao Nang if you hate repacking. Compare Ao Nang against Railay stays early; prices swing hard with the seasons.
Fill the days without stacking them. One for the Phi Phi and Maya Bay speedboat run — expect around 1,200–1,700 baht plus a 400 baht national park fee paid in cash at the pier (check Maya Bay is open — it takes an annual conservation break). One for Railay’s beaches and the red-clay scramble to the lagoon viewpoint. One inland, for the Emerald Pool and the hot spring waterfall. And one of nothing at all, which is the day you will still be talking about in December. If islands are the whole point for you, our 7-day Andaman route pushes further down the coast; if you would rather a bigger base with its own airport, start with where to stay in Phuket. Background lives in the Krabi province profile.
Days 13–14: finishing your Thailand itinerary back in Bangkok
Fly to Bangkok on the morning of day thirteen — about an hour and twenty minutes — and do not book your flight home for the same day out of Krabi; storms and schedule shuffles are real, and the buffer night doubles as a farewell party. Spend it on a rooftop drink you have earned and the mango sticky rice stall you now have opinions about. Day fourteen: airport, home, and two weeks of showing everyone your photos whether they asked or not.
How much does 2 weeks in Thailand cost?
Excluding international flights, per person, three honest tiers:
- Shoestring: expect around 1,500–2,000 baht a day — hostels or fan rooms, street food (not a downgrade here, ever), songthaews and public boats. Roughly 25,000 baht for the fortnight.
- Midrange: around 3,500–5,000 baht a day — air-conditioned hotels with pools at 1,200–2,000 a night, the tours above, massages, several flashy dinners. Call it 50,000–70,000 baht all in.
- Flash: from 8,000 baht a day — riverside icons in Bangkok, a Railay resort with the cliff view, private longtails.
Season moves both price and weather. November to February is dry, relatively cool and peak; the Andaman turns rough and wet roughly May to October. Our month-by-month guide to the best time to visit Thailand breaks down the trade-offs, and the Tourism Authority of Thailand lists festival dates worth planning around — Loy Krathong in Chiang Mai, usually November, is worth building an entire trip on.
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FAQ: planning a Thailand itinerary for 2 weeks
Is 2 weeks enough for Thailand?
Enough to do three regions properly — city, mountains, sea — without the trip feeling like a layover. It is not enough for all that plus Isaan, the Gulf islands and a jungle trek, so resist the urge to bolt bits on. Depth beats box-ticking here, and the country is not going anywhere.
How much does 2 weeks in Thailand cost for two people?
For a midrange couple, expect around 100,000–140,000 baht total excluding international flights — very roughly £2,300–3,200 at current rates. The big levers are hotel tier and how many boat tours you stack; the food stays gloriously cheap at every level.
Should I choose the Gulf or the Andaman for the island leg?
Between November and April, the Andaman — Krabi, Railay and Phi Phi at their calmest and clearest. From roughly June to September the pattern flips: the Gulf side (Koh Samui, Koh Phangan) sits in a drier pocket while the Andaman takes the monsoon, so swap the final leg south-east.
Are internal flights in Thailand worth it?
On long hops, yes, without hesitation. Bangkok to Chiang Mai is a genuine toss-up because the sleeper train is a pleasure in its own right, but Chiang Mai to Krabi by land eats more than a full day of a thirteen-night trip. A two-hour flight for a few thousand baht is the easiest sum you will do all fortnight.
What is the best month for this exact route?
November or February. Both give dry skies across all three regions, Chiang Mai at its coolest and an Andaman flat enough for every boat trip to run. December and January work too, at peak prices and crowds; April is a furnace with a water fight at the end of it.
