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Need Help with my Thailand Itinerary

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My wife and I are going to SE Asia for the first time this November (17 nights). I would like hear feedback on my schedule. This is my first post so I apologize in advance if my itinerary makes no sense. Here it is:

Day 1: Leave Chicago at 2:00pm (Night 1 on plane)

Day 2: Arrive in Bangkok at 11:55pm (Night 2 Hotel: Undecided)
Day 3: Bangkok (Night 3 Hotel: Undecided)

Day 4: Leave for Chiang Mai (Night 4 Hotel: Undecided) (Nov 17 is Loy Krathong Holiday)
Day 5: Chiang Mai (Night 5 Hotel: Undecided)
Day 6: Chiang Mai (Night 6 Hotel: Undecided)

Day 7: Leave for Luang Prabang (Night 7 Hotel: La Residence Phou Vao)
Day 8: Luang Prabang (Night 8 Hotel: La Residence Phou Vao)
Day 9: Luang Prabang (Night 9 Hotel: La Residence Phou Vao)

Day 10: Leave for Siem Reap (Night 10 Hotel: La Residence D'Angkor)
Day 11: Siem Reap (Night 11 Hotel: La Residence D'Angkor)
Day 12: Siem Reap (Night 12 Hotel: La Residence D'Angkor)

Day 13: Leave for Bangkok (Night 13 Hotel: Undecided)

Day 14: Leave for Krabi (Night 14 Hotel: Rayavadee in Railay Beach)
Day 15: Krabi (Night 15; Hotel Rayavadee in Railay Beach)
Day 16: Krabi (Night 16; Hotel Rayavadee in Railay Beach)

Day 17: Leave for Bangkok (Night 17 Hotel: Undecided)

Day 18: Leave for Chicago (Arrive same day to Chicago because of time change)

Total:

3 nights and 3 days in Chiang Mai
3 nights and 2.5 days in Luang Prabang (.5 taken off for travel and customs)
3 nights and 2.5 days in Siem Reap (.5 taken off for travel and customs)
3 nights and 2.5 days in Krabi (.5 taken off for travel and speedboat transfer to hotel)
4 nights and 2 days in Bangkok

Do you think this is too much or is it doable? Is there a way of getting from Siem Reap to Krabi directly? Do I need more time in Bangkok? What hotels would you recommend in Bangkok and Chiang Mai? Thanks for the help!!

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