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Planning a 2-week trip to Thailand in mid-August

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Hello everyone!
My wife and I are planning a trip to Thailand in mid-August. We are celebrating our 1st year wedding anniversary, and I’m planning it to be a “second honeymoon”
I’m planning to be there in Mid August (most probably 9-22), the trip will begin and end in Bangkok. I know it’s not a lot of time, that’s why I’m planning to be as efficient as possible. I’ll be using flights to move from one place to another to save time.
My main interests:
- We don’t like crowded cities, we prefer to be in open places, nature, forests and beaces. That’s why I’m not planning to stay in Bangok for many days.
- NOT interested in: temples, night clubs and activities, full moon parties etc…..
- I’m not that interested in spending much time on beaches, but staying in a clean, calm beach is a must and mostly enjoying the scenery
- Adventures and trips –I read about many outdoor activities that can be made in the various parts of Thailand, and we’re very interested in that
I’ve never been in Thailand before, but I travelled quite a lot. I read lots and lots of material, websites, guides, itineraries, and I came up with a preliminary plan for the trip, but I need your expert advices.
The main issue I read about is the weather – I know it’s not the ideal season to travel to Thailand, but we’ll live with that. I understand that we’ll have to be ready to lots of rain, but hopefully, we will have plenty of sunny days too.
I also understand that the north (Chang Mai) will be very rainy, and because of the season, I should avoid the southwest (Phuket, Krabi…) and opt for the better weather in the southest Gulf (Koh samui, Ko Phangan….)
So far, I came up with these 2 itineraries, and I’m more inclined towards the first one because of the weather:

Itinerary 1:
1. Bangkok (3 nights) – arrival, main attractions, traditional markets, shopping. I think it will be enough, as we really don’t like crowded and big cities. I also prefer staying in a more calm part of the city.
Possible accomodations:
o Peninsula
o Chatrium Hotel Riverside
o Banyan Tree
o The Okura

2. Ko Samui (5 nights) – direct flight from Bangkok to save time. Here I’m planning to enjoy the beaches, nature and outdoor activities and trips.
Possible accomodations:
o Lanna Samui
o Code
o Khwan beach resort

3. Ko phangan / Ko Tao (5 nights) – I’m still undecided which island to choose. Here we’re planning to relax, stay in a pool villa, away from the crowded places. I know that Ko Phangan is bigger and has more possibilities, but I’m afraid it will be too crowded. Ko Tao should be calmer, and hotels are cheaper.
Possible accomodations:
o Ko Pangan:
 La divine comedie
 Panviman Koh Phangan
 Kupu Kupu Beach Villas & Spa
o KO Tao
 The Place Luxury Boutique Villas
 The Rocks Villas

Itinerary 2:

1. Bangkok (3 nights)
2. Chiang Mai (5 nights) – I am SURE we will be enjoying the countryside, the villages and the rural areas, and the various activities in Northern Thailand, but I’m afraid of the weather that might ruin the whole stay. So I’m reluctant about it.
3. Ko Samui (5 nights)

Now the questions:

1) What do you think about the itineraries in general? Maybe I’m missing something, maybe I should choose other islands, or stay more on one of them?
2) Should I opt for the safer 1st itinerary, or should I still go for the 2nd one and not miss Northern Thailand
3) Hotels- how are the ones I’m considering? Are there any others recommended, still with reasonable price?
4) Ko Samui/KoTao back to Bangkok – My flight back home will be from Bangkok in the morning (~9:00AM). How should I plan my way back from the southern islands by flight? When I should be heading back from the islands to be in Bangkok airport in a safe time frame?
5) Keeping Bangkok to the end – some suggested to head directly to the islands, and come back in the end to Bangkok before travelling back home. What do you think? I’m not planning to buy a lot in Bangkok, and I’d like to finish the trip in the quiet islands instead of Bangkok.

Any advice, suggestions or idea will be gladly welcome, so we can enjoy the trip as much as possible :)
Thanks in advance!!

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