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Singapore, Malaysia, and then Thailand for an entire month

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Hi, my wife and I (both 29) are going to start a 6 month journey in SE Asia. So far this is what we have:

1) Singapore
2) Bus to Kuala Lumpur
3) Bus to Penang
4) Fly to Phuket - beginning of April
5) Ferry to Koh Phi Phi
6) Fly to Koh Samui
7) Ferry to Ko Phang nan
8) Ferry to Ko Tao
9) Flight to Bangkok (from Koh Samui)


Questions:

1) How long should we stay in each?
2) Did we miss something incredible on the list in Thailand?
3) Penang or Langkwai?
4) I have a shellfish allergy and plan on getting a laminated card in Thai that says "NO SHELLFISH". Will I be ok in the Land of Smiles?

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