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Itinerary help- Singapore, Thailand, Cambodia, Philipines

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Hello,
My friend and I are planning our 1st trip to SE Asia. We plan to arrive Dec 31 (celebrate New Years at the destination) and return Jan 16. Need to be in Manila Jan 6-9 for a wedding.

We were considering arriving in Singapore and staying for 3-4 days, which leaves 2 days before heading to Manila.

It is most important for us on this trip to see the culture vs beach. A couple beach days at the end would be fine.

Questions:
1) Does arriving in Singapore for 3-4 days make sense, knowing we have 2 days to spare before Manila? If so, any suggestions for locations ok for americans? Any other suggestions for arrival country?
2) We would love to cover all 4 countries- is this realistic?
3) What is travel time between BKK and Chiang Mai? Phuket/Ko Samui? And what are modes of transportation available?
4) What is travel time between Phnom Penh and Siem Reap? What modes of transport are available?

Any itinerary suggestions you may have are much appreciated.

Thank you,

Trvl7

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