help me pick between these 2 itinerary's
 

Itinerary 1
arrive BKK 7/23 and fly immediately to KS
KS 7/23 7/24 7/25 7/26 7/27
fly to CR and get car ( stay at Anantara) 7/28 7/29 7/30
drive to CM 7/31( drop older daughter at community service project)8/1 8/2 8/3 8/4 8/5 8/6 pu daughter AM of 7/28
fly to BKK 8/7 8/8 8/9 8/10 8/11 8/12 and leave for JFK midnight 8/12


Itinerary 2
fly to BKK 7/23 and fly immediately to KS
KS 7/23 7/24 7/25 7/26 7/27 7/28 7/29
fly to CM drop daughter at community service afternoon 7/31,8/1 8/2 8/3 8/4 8/5 8/6 pu daughter AM of 8/7
fly to BKK 8/7 8/8 8/9 8/10 8/11 8/12 and leave midnight 8/12

Would Bangkok air pass work for either or better to do this on individual airlines??

How confusing is this...what do these initials stand for? Many of us are reading fast as we're very busy and need to be able to read these questions easily. So, CR and CM must be Chiang Rai and Chiang Mai. But, what the heck is KS and what does "pu" daughter AM, mean? It's like reading code. Happy Travels!

I'd do something similar to the first option, where you spend time at the Anantara. Note that Bangkok AIr doesn't fly to CR, so you may want to consider budget airlines like Air Asia or Nok Air. Bangkok Air is the only airline that flies to Ko Samui, so you are stuck with an expensive flight.

pu daughter=pick up daughter is my guess.

I agree with Kathie that the first looks a little better.

Sorry for the sloppy post- very tired last night but no excuse. Will likely do 1st itinerary but trying not to get killed with domestic airfare. would it be best to use discovery airpass to do
bangkok to koh samui
koh samai to chiang mai ( then drive to and from chiang rai)
chiang mai to bangkok
Is there a better way to do this??

You airfare problem is the flight to/from Koh Samui. Bangkok Air owns the airport, so the price is high. One option would be to choose a different beach. Hua Hin is a 2.5 hour drive from Bangkok, so would cut down on your airfare. You could fly a budget airline like Air Asia or Nok Air for your other legs.