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Help with SEA Retirement Trip

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I think I have a doable plan for a 3 month trip to SEA. Any critique appreciated.

Oct. 19 Seatttle to Bangkok
Oct 20-25 Bangkok
Oct.26 fly Krabi
Oct. 27-31 Koh Lanta (good deal at Layana right before high season starts)
Nov.1-6 explore southern beaches
Nov. 7 fly Bangkok for overnight
Nov.8-13 Siem Reap
Nov. 14 Bangkok overnight
Nov. 15 Train to Chiang Mai
Nov. 15-21 Chiang Mai (meeting family)
Nov.22-28 Mae Song Loop, possible trek
Nov. 29-Dec. 5 Chiang Mai to Luang Prabang
Dec. 6-12 Luang Prabang
Dec.. 13-19 trek north of LP
Dec 20 overnight LP
Dec. 21 fly Vientiane
Dec 21-23 Vientiane
Dec. 24 fly Bangkok
Dec. 24 overnight Bangkok or better yet catch a flight to Singapore same day
Dec.25-29 Singapore
Dec. 30-Jan 1 Penang
Jan. 2-3 KL
Jan4-14 Java ( intrigued with ferry from eastern Java to Bali)
Jan.14-23 Bali (basing in Ubud area)
Fly home from Singapore if Bali prohibitive)

Any huge flaws in my thought process? Tried to fit in a lot of our bucket list with what seems like plenty of time in each place to relax.
Thank you.....

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