My boyfriend and I will be in Thailand/Cambodia in late Jan/early feb for 3 weeks. Our itinerary is a bit split up because we are attending a wedding in Bangkok. We will have 6 nights in Chiang Mai/Golden Triangle region and are debating whether to stay in the city of Chiang Mai or at Baan Rai Lanna, which has been highly recommended here or at Baan Orapin, which is also has great reviews. We live in NYC, so being out of the city appeals to us more but I don't want to limit our opportunities to do more interesting/active tours by being so far out of town. We are both in our early 30's and pretty active, although not overly rugged. We've both traveled a lot, but this is our first time in Asia. Our itinerary is as follows. Please weigh in!

Jan 20 Bangkok—Peninsula
Jan 21 Bangkok—Peninsula
Jan 22 Chiang Mai—Baan Rai Lanna or Baan Orapin
Jan 23 Chiang Mai—Baan Rai Lanna or Baan Orapin
Jan 24 Chiang Mai—Baan Rai Lanna or Baan Orapin
Jan 25 Golden Triangle—Anatara
Jan 26 Golden Triangle—Anatara
Jan 27 Golden Triangle—Anatara
Jan 28 Bangkok—Peninsula (Pre-wedding dinner)
Jan 29 Bangkok—Peninsula (Wedding)
Jan 30 Phuket—Benyada Lodge (with wedding group)
Jan 31 Phuket—Benyada Lodge (with wedding group)
Feb 1 Phuket—Benyada Lodge (with wedding group)
Feb 2 Phuket—Benyada Lodge (with wedding group)
Feb 3 Siem Reap—Le Meridien (on starpoints)
Feb 4 Siem Reap—Le Meridien (on starpoints)
Feb 5 Siem Reap—Le Meridien (on starpoints)
Feb 6 Bangkok—Peninsula
Feb 7 Bangkok—Peninsula
Feb 8 Bangkok—Peninsula
Feb 9 NYC!

Since you are going to be at the Anantara I would suggest staying in town at Baan Orapin. You can always hire a driver (Poon is excellent) if you want to spend time out of the city during the day (which I would recommend). But it's nice to be able to walk around or take a quick ride in the evening for dinner, shopping etc.

i think it looks fabulous as it is and agree with gloria....

chiang mai is a big low rise city btw...

BTW-- I lived in New York (Manhattan for 30 years) and lived another 30 years in Chicago so I am a "city" person. Chiang Mai is NOT a city that will in any way remind you of NYC. Bangkok may but definitely not Chiang Mai which is one of the reasons I love it so much.

Staying at the Anatara is a very good suggestion. The itinerary looks fine. You can search the board for things to do in CM. We found 4 full days was maximum ideal visit including 30-50 mile day trips.
At the Pen the Deluxe Room category just below the one with the balcony is really quite large and nice. You can even request between 20-25 floor which is a good to get a panarama.

Thank you all so much! It turns out the Anatara is booked for Jan 25, the night we wanted to add, so maybe now we'll try 2 nights Baan Orapin, 2 night Baan Rai Lanna and 2 nights Anatara? Is that too much moving? Or do we find another hotel for a 3rd night in the Golden Triangle? Do you have contact info for Poon?

So I think we've decided on 2 nights each in 3 places.
Jan 22 Chiang Mai—Baan Orapin
Jan 23 Chiang Mai—Baan Orapin
Jan 24 Chiang Mai—Baan Rai Lanna
Jan 25 Chiang Mai—Baan Rai Lanna
Jan 26 Golden Triangle—Anatara
Jan 27 Golden Triangle—Anatara
Jan 27 Golden Triangle—Anatara (our BBK flight is 4pm)

Is this too much moving around? We'd have preferred to stay 3 and 3, but that doesn't seem workable with Anatara having no rooms on the 25th. Also we plan to take a cooking class in Chiang Mai. Can anyone recommend a good place? Also, it seems like there is so much to do everywhere! We are thinking of saving the elephants for Anatara and perhaps the hilltribe visit. We may do the cave/waterfall hike and rafting at Baan Rai Lanna and and a temple visit/cooking class/night market while at Baan Orapin. Feel free to ammend, tweak and suggest! Any guide or driver suggestions are appreciated too...for Norther Thailand or our trip overall. Thank you so much!

Oops! I meant we leave Anatara at 4 pm on Jan 28th!