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Cambodia/Thailand in 2 Weeks - First Trip

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My wife and I are starting to plan a trip for our 25th anniversary - we also both turn 50 this year, so something memorable is due. We want to do Thailand and Cambodia but only have the last two weeks on November to take as a vacation. We want to experience as much as possible but at a reasonable pace. We are both in good shape, so lots of walking and hiking isn't an issue. We are more into sightseeing than resorts, but would like to end the trip with a few days on one of Thailand's beaches.

So far I have identified the following places: Bangkok, Siem Reap (Angor Wat), Chiang Mai and Koh Samui (or other location with a beach to end our trip before heading back to Bangkok). Don't have more than that for the moment, and would be interested in suggestions for a reasonable itinerary, timeline, how to get from one city to another (Discovery Pass by air?) and accommodations. I assume Bangkok is where most everyone starts and ends? Are there beach areas to avoid at the end of November because of unsettled weather. I read somewhere that the rains can extend through November in Krabi and to head to the Gulf side instead.

Sure to have more questions as we continue our planning.
Many thanks!

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