I have 2 weeks in January
thoughts of which cities to visit /things to see
In two weeks I would suggest Bangkok, Ayutthaya, Sukhothaya, Chang Mai, Chang Rai, Hua Hin and if you can get to some elephant camp I strongly recommend to visit. It is unbelievable what these animals can do. What to see: temples, markets and just local life as it goes.
If you care about animals then be very wary of visiting an elephant camp or elephant refuge. Do your homework to make sure it is reputable.
Great time of year.
If you want beaches, spend a few days in the south. There are temples and other sights too. There are opportunities for snorkeling (tropical fish).
Chiang Mai for sure. 4-5 days is not too much, there are day trips to interesting places. Definitely go to an elephant refuge, not one of the parks (where you ride them and/or watch them do tricks) that exploit the animals. Chiang Rai is reasonably close by car or public transportation and another interesting area for 2-3 days. I had a private guide with a car to tour around Chiang Rai for 2 days around the border areas, on the last day we toured along the way to Chiang Mai and he dropped me at my hotel.
Take cheap flights both north and south. Trains and buses are slow, uncomfortable and not necessarily on schedule.
There's a lot to see and do in Bangkok itself, 3-4 days minimum. A popular side trip is to fly to Siem Reap for 2-3 nights to visit Angkor Wat.
Agree with Chani's advice. Suggest a visit to the Elephant Nature Park, a rescue and rehabilitation facility near Chiang Mai, in which you can spend much time with elephants. Also, you may consider a private guide for some of your time. We did so, and visited incredible villages and sights, not on the tourist circuit and was quite affordable. Send a private message to me if you wish more information.
I am interested how to find guides
Ph
My guide in Chiang Rai was Jermsak and he was terrific - very flexible, excellent English, great sense of humor, as well as knowledgeable about everything. You can get more info from his website
In Bangkok and Chiang Mai I didn't need a guide, though there are places that I'm sure I would have been able to visit with a guide+car.
In Bangkok we took a trip with Amazing Bangkok Cyclist (http://www.realasia.net/).
Cycling in Bangkok is a different experience from walking or driving in a tour bus. You can get in to places no bus can get to.
Note: Even when we crossed big roads we felt completely safe.