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Draft itinerary - appreciate some input

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Hi there

Planning to spend 3 weeks or so in Thailand and Laos and have so far booked fares to Bangkok only. We will arrive on 2/2/2014 at about 8.00 pm.
Here's the rough plan:
3 nights Bangkok ( we have been twice before) to get some glasses and clothes made.
5 nights Chiang Mai (we have a friend of a friend living there and plan to leverage his local knowledge)
3 nights Chiang Rai (some trekking perhaps and elephants)
Get to Chiang Kong for Luang Say two night cruise to Luang Prabang spend 5 nights in LP, 1 night in Vang Vieng, then 2 in Vientiane, fly to Bangkok.
Questions:

1.We'd like to take a boat from Bangkok to Ayutthaya in the morning, see the temples and then pick up the train to Chiang Mai at about 9.00 pm, is it feasible to take luggage with us on the tour boat ? Would there be somewhere safe to leave it ? Maybe left luggage at the train station??? There will be one small and one medium wheeled suitcase.

2.From CM to CR we are thinking of hiring a car and driver to take us to Tha Ton to pick up the daily 12.30 pm boat to CR. How long does that drive take, and is it relatively easy to hire a car & driver? What should we roughly pay ?

3. Best way of getting from CR to Huay Xai for Luang Say boat which departs at 9.30 am (although you are asked to be there at 8.30) including getting visa on arrival ? Again I was thinking of car and driver, how long is the drive ? May have to stay the night on the border, would you recommend Chiang Kong or Huay Xai ?

4. Any suggestions for guest house type luxury accomodation in Q3 ?

We like boats and trains, not bus travel much and have been to SE Asia a fair bit in the past 9 years.
Thanks for any answers or suggestions !

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