14 Days in Thailand: The Perfect Bangkok, Ayutthaya, Chiang Mai & Phuket Itinerary

At ten o'clock at night, from a boat, the ruins start to glow.

Wat Chaiwatthanaram comes out of the dark first — a Khmer-style tower ringed by eight chapels, floodlit gold, standing there since 1630. And empty. No coaches, no queue, no ticket line. Just black water, the heat still coming off the day, and the burnt-out capital of an empire that was one of the largest cities on earth until an army levelled it in 1767.

That was night five of fourteen. By then I'd given up trying to describe Thailand in messages home.

Here's the thing I'd have got wrong on my own: I'd never have stayed the night in Ayutthaya. Every guide tells you to do it as a day trip from Bangkok, so you go at noon with two thousand other people, and you never find out that the ruins are lit after dark and that almost nobody is there to see it.

So this post is not just about where to go on a two-week Thailand itinerary. It's about why the shape of it matters — and how we stopped agonising over that shape and let it be built for us.

The route at a glance

Bangkok (3 nights) → Ayutthaya (2 nights) → Chiang Mai (4 nights) → Phuket (5 nights)

Fourteen nights. Four completely different Thailands: a megacity, a ruined royal capital, the northern mountains, and the Andaman coast. Best run November to March, in that order, finishing at the beach.

That split — 3 / 2 / 4 / 5 — is the whole trick, and we didn't invent it. We answered nine questions on DIYTravel about who was going, how long we had, what kind of weather we wanted and what sort of places we actually like, and this came back at the top of the list marked Top match: already sequenced, already divided into nights, already built for the dry season. We looked at it for about a minute and said yes.

Days 1–3: Bangkok

Stay on the river. That's the one piece of advice I'd press on anyone, and it was in the plan before I knew to want it: from a Chao Phraya pier you're a boat hop from the old city, and you never sit in the traffic that makes people say they didn't like Bangkok.

Wat Arun is the one that stops you mid-sentence. Cross on the little ferry and the Temple of Dawn goes from a postcard silhouette to something much stranger up close — the whole spire is encrusted in broken Chinese porcelain, millions of shards of it, pressed into flowers. Go late afternoon, climb the steep steps while the light is going, and then cross back and watch it light up from the far bank with a drink in your hand.

Bangkok is a city of markets, and they are all better after dark. Yaowarat, Chinatown, becomes a corridor of charcoal smoke and plastic stools — grilled scallops, ba mee noodles from a man who has clearly made nothing else for thirty years, mango sticky rice eaten standing up at eleven at night. The night markets proper are an evening each: the train-yard sprawl of vintage stalls and neon bars, the riverside ones where you eat with the water going past. My wife, who had been dubious about the whole street-food thing, ate more than I did.

Then the other Bangkok, twenty minutes and a century away. IconSiam is a riverside mall the size of a small airport, with an entire indoor floating market on the ground floor — wooden boats, tiled canals, vendors cooking from the hulls, air conditioning. It is completely absurd and completely brilliant, and the free shuttle boats run from the central piers.

And yes, we did the rooftop. The Sky Bar at the top of State Tower is the one from The Hangover Part II — sixty-three floors up, open to the sky, a circular lit bar cantilevered over the drop. It is not a secret and it is not cheap, but standing on the edge of that terrace watching the river bend away through the whole lit city is worth one expensive drink. Long trousers and proper shoes, or you won't get in.

The day we went west to Kanchanaburi was the one I'd have cut if I'd been planning this myself, and it turned out to be one of the best. You swim in the Erawan waterfalls — seven turquoise tiers, and you can actually get in, which in that heat is not a small thing — and then you stand on the bridge over the River Kwai and the day turns very quiet. The museum by the war cemetery is small and unsparing. Go.

Days 4–5: Ayutthaya, the ruined capital

Most people do Ayutthaya as a day trip from Bangkok. Give it two nights instead. It took us about four seconds to stretch it in the app, and it is the best decision we made all fortnight.

Stay on the island, inside the ring of rivers. The old capital is completely flat, so you hire bicycles and the whole ring of temples becomes one easy loop with a little ferry crossing in the middle. You ride between eight-hundred-year-old chedis in a t-shirt, past someone's washing line, and stop for iced coffee. It is the least museum-like UNESCO site I have ever been to.

Two things to do properly. Wat Mahathat first thing, for the sandstone Buddha head cradled in the roots of a fig tree that grew around it after the city fell — crouch to meet its eye line, as the signs ask you to. And Wat Chaiwatthanaram last thing, from the water, after dark. That hour is the entire reason to sleep here instead of day-tripping.

Days 6–9: Chiang Mai and the north

North to the old Lanna kingdom. There's a famous sleeper train and there are hour-long flights, and honestly it doesn't matter which you choose — we flew one way because we wanted the morning.

Chiang Mai is where the trip changes temperature, literally and otherwise. Stay inside the square moat and everything is walkable: the temples, the night bazaar, the Sunday walking street that takes over the whole old town.

Set one alarm you won't want to. Just before dawn the monks come out barefoot in single file to collect alms, and the street you walked down drunk on noodles the night before turns into something else entirely — kneeling neighbours, rice going into the bowls, a low chant, and then they're gone and the city starts its day. Stay low, don't block the line, don't point a camera into anyone's face. Afterwards, sit in on the morning chanting at one of the old teak temples inside the moat. Several of them run a "monk chat" later in the day where novices practise their English and will answer absolutely anything. It cost us nothing and it was the most memorable hour of the fortnight.

The day at the Elephant Nature Park ran it close. It's a rescue sanctuary — no riding, no hooks, no performances. You feed them, you walk with them, you watch a forty-year-old elephant lower herself into a mud bath with the enthusiasm of a labrador. Nobody makes them do anything. I hadn't realised how much I'd been bracing for the alternative until it didn't happen.

Eat two things here. Khao soi, the north's own dish — coconut curry broth, egg noodles soft underneath and crisp on top, pickled mustard greens cutting through the richness; we had it four times in four days and I still think about it weekly. And the giant river prawns, split and grilled over charcoal until the shells blacken, served with a fierce lime and chilli sauce. They come to the table the length of your forearm, you wear the bib, you give up on dignity. Worth it.

The long day out to the White Temple and the Blue Temple at Chiang Rai is three hours each way and worth every minute. The White Temple isn't ancient at all — it's a contemporary artist's ongoing work, mirrored white, deranged and beautiful. The Blue Temple down the road is cobalt and gold inside and feels like standing in a held breath.

Days 10–14: Phuket and the Andaman coast

You want the end of a trip like this to be a full stop, and five nights on the Andaman coast is exactly that. The plan put us at Kata and Karon — the middle of Phuket's west coast, swimmable sand and sunset restaurants, with Patong's noise safely up the road rather than on the doorstep. Right call.

Phang Nga Bay is the day you'll photograph most and the one photographs are worst at. Limestone karst towers straight out of flat green water, sea caves you paddle into, and the stilt village at Koh Panyee, built entirely over the sea against a cliff. We went by sea canoe rather than speedboat and drifted through a cave into a hidden lagoon with nobody else in it.

The Phi Phi Islands day is the postcard one — Pileh Lagoon for snorkelling, and Maya Bay, reopened with visitor caps that make it bearable again. Go early.

And then we did nothing. We'd pencilled in one more day out and swapped it, the night before, for the sand, a book and a plate of grilled fish — which is a legitimate use of a holiday and the thing I'd most encourage you to protect. Clearing the day took one drag.

We finished with a morning in Old Phuket Town — Sino-Portuguese shophouses in sherbet colours along Thalang Road, coffee, street art, the lantern-strung lane of Soi Romanee — and flew home from an airport forty minutes away.

Best time to visit Thailand

November to March. That's the dry season on both coasts and it's the window this itinerary is built for — hot, bright, swimmable, and the only stretch where the Andaman half reliably delivers.

April and May are punishing in the ruins and the cities. From May onwards the southwest monsoon reaches the Andaman coast, and the last five nights of this trip — the whole payoff — change character completely. DIYTravel scores every trip against the month you actually pick, which is why we were never offered a bad one.

What made the planning easy

I'm not a spreadsheet person and I refuse to become one for a holiday. Here's what I didn't have to do.

I didn't have to invent the shape. The route arrived already sequenced and already divided into nights, assembled from how these places genuinely connect rather than from a blank page.

I didn't have to accept it either. The itinerary lands as a calendar of days you can drag around. We gave Ayutthaya an extra night, traded a day out for a slow one on the coast, and added a day in Chiang Mai because four nights felt short — and the whole trip re-timed itself around it.

I didn't have to research every day from scratch. Each day has a panel of things to do at that destination, and it flags anything already sitting on another day, so nothing gets planned in twice.

I didn't have to hold the booking list in my head. Everything still to book sits in one place — stays, days out, transfers — with links straight through to the operators.

And nothing we were shown was invented for us. Every place in this post is somewhere you can go this winter.

Thailand itinerary FAQs

Is two weeks enough for Thailand? Two weeks is the sweet spot. Fourteen nights lets you pair the cultural north with real beach time without spending the holiday in transit. Ten days means dropping one of the four stops — usually Ayutthaya.

How many days do you need in Bangkok? Three nights. Enough for Wat Arun and the old city, a night market or two, and one full day out to Kanchanaburi, without burning out on the heat and the traffic.

Is Ayutthaya worth staying overnight? Yes, and it's the single best upgrade to this route. The floodlit ruins after dark and the early-morning bike loop are both invisible to day-trippers.

What's the best way to get from Bangkok to Chiang Mai? Fly if you want the time back — it's about an hour. Take the overnight sleeper if the journey itself appeals. Neither choice changes the itinerary.

Phuket or Krabi for the end of the trip? Phuket for five nights, because it gives you the Phang Nga and Phi Phi day trips, an old town worth a morning, and a major airport to fly home from. Base yourself around Kata or Karon rather than Patong.

When should I book? November to March is high season on both coasts. Stays and the better day tours go early, especially over Christmas and New Year.

Plan yours in about five minutes

Fourteen nights, four Thailands, one plan we barely had to think about.

Answer nine questions and see what comes back for you.