For September 2–October 20, prioritize northern Thailand and the Gulf Coast, where weather is generally more favorable than Phuket and Krabi during the southwest monsoon.
Bangkok — 4–5 nights
Kanchanaburi — 2–3 nights
Chiang Mai — 7–10 nights
Pai or Chiang Rai — 4–6 nights
Khao Sok National Park — 3–4 nights
Koh Samui — 5–7 nights
Koh Phangan — 4–6 nights
Koh Tao — 5–7 nights
Bangkok — 1–2 nights
If forecasts turn wet in the Gulf, replace some island time with Koh Lanta, Krabi, or Phuket, but check marine conditions before booking. Thailand’s weather is highly regional, so decide the final beach segment 5–10 days ahead when possible.