I'm feeling really called to go spend some time in Chiang Mai, however my travel plans are a bit up in the air, and I'd like to leave them that way as much as possible. I'm from the US, but I'm in Italy now and would like to leave for Chiang Mai by early June. I know I have to be in NYC by August 11th or 12th, but other than that would like to stay in Chiang Mai the whole time (so if I go now that would put me there for 2 1/2 months, or if I go in June it would be 2 months or just over that).

From my research, I could apply now for a 60 day visa but would need to leave here mid June instead to make sure I don't overstay. However it's a little bit difficut to ensure I stay exactly 60 days or less, as I have business comittments that only allow me to travel on certain days. And if I leave earlier than that I'm not sure what's possible *past* 60 days, especially if it's just barely over?

OR am I better of not even worrying about a 60 day visa and going just into the country for 30 days without a visa, and making a visa run once or twice while I'm there?

Also, I'm not sure if I'll want to go back to Chiang Mai after my time in NYC, or if I'll stay in the US for a while. How does it work if I were to want to stay for longer than 60 days? And will they let me right back in the country if I've only been gone for a week or two and can see I've been there before? Can you do visa runs indefinitely or could you get in trouble after a certain amount of time?

If I come in with a *real* departure date that's after my legal time I can stay, can my departure ticket be a train ticket to a bordering country, or does it need to be a plane ticket elsewhere that I then have to change once I'm in Thailand? For example, let's say I come in for 60 days without a visa and do already have a ticket back to the US, but the date is later than that - can they see my ticket in the system? Or can I hide it somehow and just show them a train ticket to a neighboring country to make it look like I'm moving on to travel in Asia?

Also, if visa runs are my best option, is it better to do them without a visa for 30 days each time, or get 60 day visas each time (is that even possible? And what is the best place to do visa runs from Chiang Mai?

I hope all of my random questions make sense Thanks in advance for your support in this!
<3

If you get a single entry tourist visa it will give you an entry for 60 days that can be extended for 30 days.

You could enter without a visa and get a 30 day visa exempt entry that can be extended for 30 days at an immigration office. The airline may ask to see a ticket out within 30 days of arrival to board the flight. You could buy a one way ticket to a nearby country on a low cost carrier to show them.

The airlines normally will not accept anything other that a ticket by air.

Immigration does not ask for onward tickets when you arrive.

Thank you!! Do you know how much a 60 day entry visa costs and if there's a fee for the 30 day extension? And if I arrive on the 60 day and want to extend it, will they still need to see the departure ticket within 60 days, or will they be okay with it within 90 days if I'm applying for an extension?

Also, do you have any clue how I'd go about applying for the 60 day visa from Italy if I'm a US citizen? The only embassies I see are a 5 hour drive from me. Ideally I'd love to be able to take care of it all online if I can, and worst case scenario in my current city (Ancona, Italy).

A single entry tourist visa costs the equivalent of 1000 baht in the local currency where you apply for it. The extension costs 1900 baht.

Some embassies and consulate will want to see a ticket out of the country. Some will accept one up to 60 days and other 90 days.

If you have a visa you do not need to show the airline a onward ticket.

There are 4 honorary Thai consulates in Italy where you could apply. http://www.guidetothailand.com/thailand-travel-information/honcon-europe.php

There is also the embassy in Rome. http://www.thaiembassy.it/