Two seas with opposite weather, a dozen islands worth the ferry, and the crossings that get you there.
Find a room before you go.
Thailand has islands on both sides of the peninsula, and the single most useful thing to know is that their seasons do not line up. The Andaman coast in the west — Phuket, Krabi, Koh Lanta, Koh Lipe — is at its best from November to April and takes the brunt of the southwest monsoon from May to October. The Gulf islands in the east — Samui, Phangan, Tao — stay dry much longer into the summer, and get their heaviest rain in October and November.

That single fact rescues a lot of trips. If your dates fall in the European summer, go to the Gulf. If you are travelling at Christmas, the Andaman side is the safer bet. And if the forecast looks grim on one coast, the other one is a five-hour drive away — the peninsula is narrow.
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From this coast, the Gulf islands are the easy ones. Trains run south from Ban Krut to Chumphon in about two hours, and the Lomprayah catamaran leaves Chumphon pier for Koh Tao in an hour and forty-five minutes, carrying on to Koh Phangan and Koh Samui. Further south, Surat Thani and the Donsak pier are the gateway for the car ferries to Samui and Phangan.
For the Andaman islands, cross the peninsula. Buses and minivans run from Surat Thani to Krabi and Phuket in three to four hours, and from Krabi the boats leave for Koh Lanta, Koh Phi Phi and the Phi Phi day trips. Koh Lipe, far to the south, is reached from Pak Bara pier in Satun.
Book ferries the day before in high season, especially around the full moon. Outside those weeks you can usually walk up to the pier and buy a ticket for the next departure.


The big one: an airport, real restaurants, and beaches for every budget. Koh Samui guide →

Famous for the full moon, quiet as a monastery on the north coast. Koh Phangan guide →

The dive island: cheap certifications, clear water, small enough to walk. Koh Tao guide →

Forty-two limestone islands off Samui, best seen from a kayak on a day trip. Day trips from Samui →

One island per week is a good rhythm. Ferries eat half a day at each end, and the islands are more different from each other than the brochures suggest: Tao is a village, Samui is a small town, Phangan is both at once depending on which coast you pick.
Gulf side and Andaman side, big and small — thirteen islands with their own page.