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Thailand is the bigger, busier, more varied trip. Sri Lanka is the smaller, quieter, more concentrated one.
Both escape a British winter, both run about a fortnight, and both end at the beach. What separates them is scale — and, practically, whether you want to fly around a country or drive across a small island.
In short
Thailand — fourteen days. Three days in Bangkok, then the Maeklong railway market and Amphawa's floating market, the River Kwai at Kanchanaburi, and Ayutthaya. North to Chiang Mai for the Lanna old city, a meeting with a monk, an elephant clinic and a rescued elephant sanctuary at Mae Wang. Then the rainforest at Khao Sok and three days on Koh Samui.
Sri Lanka — fifteen days. Colombo, then the Dutch fort at Galle and a mangrove river safari; an elephant safari at Udawalawe; three nights in the hill country at Ella with the tea-country train and a night in a working tea factory; Kandy; the rock fortress at Sigiriya; the ancient cities of Polonnaruwa and Anuradhapura; and three days by the sea at Trincomalee.
Thailand covers more ground and more kinds of place. Sri Lanka covers one island thoroughly.
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This is where the two genuinely diverge, and it settles the choice for a lot of people.
Sri Lanka has steps. Sigiriya is a climb of several hundred, including exposed metal staircases bolted to the rock — optional, and travellers do sit it out, but it is the trip's headline sight. Temples throughout mean more steps, on uneven stone, in bare feet on ground that has been in the sun. The hill-country walk to Little Adam's Peak is gentle.
Thailand has almost none of that. City walking on flat ground, temple steps in ordinary shoes, and a rainforest with uneven paths. The most demanding thing on the itinerary is the heat.
We have written Sri Lanka's demands up honestly in how physical is Sri Lanka. If steps are a real difficulty, that page is the more useful one, and Thailand is probably your answer.
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Wildlife: Sri Lanka. Not close. Udawalawe is famous for its elephant families and rarely disappoints, and there is a mangrove river safari and a night safari at Polonnaruwa as well. Thailand's animal days are the elephant clinic and sanctuary near Chiang Mai — moving, ethically careful, and not wildlife viewing in the same sense. See what to expect from Sri Lankan wildlife.
Food: Thailand. Also not close. Thai food at home is one of the world's great everyday cuisines, and there is a cooking class in Chiang Mai. Sri Lankan food is excellent and much less known — hoppers, curries, the tea — but Thailand wins this one.
Beach: a draw. Koh Samui gives you three days including a full day off. Trincomalee gives you three days at the end and a coastline most people have never heard of, which is its own argument.
Cities: Thailand. Bangkok is a great world city. Colombo is a stop rather than a destination.
Choose Thailand if you want variety, the food, a proper city, and the gentler trip physically. It is also the better first trip to Asia for most people.
Choose Sri Lanka if you want wildlife, if you would rather not fly internally, if the idea of covering a whole country by road appeals, or if you want the hill country and the tea — which is the part travellers most often come home talking about.
A note on timing. Both are governed by monsoons, and Sri Lanka's are unusual: two of them, hitting different coasts at different times, which is why the island is workable somewhere year-round. Thailand's cool dry season is the comfortable window. Our departures on both sit inside the sensible months.
Both trips are land-only, take a maximum of 12 travellers, and every departure is guaranteed — it goes ahead regardless of how many others have booked. If you are weighing the wider region, which Asian country to visit first sets them all out.