At least from the US, the e-visa process for a 60-day visa is fantastic. Like, I submitted for a 60-day tourist visa around 4 pm on a Monday afternoon earlier this month, and
So, given that you’d be coming in November, I think getting a single-entry tourist visa for 60 days would be pretty easy, and then you could extend it in Chiang Mai — Northern Thailand is especially nice in November and December, and there are also several language schools if you’d like to learn a little Thai — for another 30. At that point, you could leave the country and return for another thirty days without a visa, and extend that visa-exempt visit for another 30 at immigration. Once that 60-day total was up, you’d have to do another exit and enter again. (You could also do
*****
/60 instead of
*****
/30 or
*****
/60 depending on how you wanted to time your visa extensions and your trips to other countries.)
As others have pointed out, there’s also a multi-entry tourist visa that’d give you three sixty-day entries, each of which could be extended for an additional 30 days. But I’ve never gotten one of those myself, so I’m not sure the application process is as easy. And you’d still need to do at least one border run (or two, if you want to completely avoid applying for extensions while you’re in Thailand). And there are language schools and Muay Thai trainings that could do an education visa (maybe even some of the massage schools, too), but those would have specific training requirements that might not fit your preferences as a tourist.
One note on the border run front: by February, or even January if you’re sensitive, you might start seeing the effects of burning season, so that might be a good time to do a flight to Vietnam or Malaysia or Singapore, and then fly back to Bangkok instead of Chiang Mai when you return to Thailand. (Chiang Mai is awesome for both December 31 and the Chinese New Year, but I bet Bangkok’s Chinatown would be pretty fun, too. There’s also a Chinatown branch of
with container boxes that are perfect for storing a suitcase worth of whatnot for about $5 a month — you can also just do luggage storage or rent larger lockers from them, but the container box is the best deal I’ve found in Asia so far — so that makes Bangkok a great entry/exit point if you don’t want to keep lugging all your stuff across borders.) If you’re doing a border run in March, when the burning season typically gets more intense, Ubud (Bali) can be a particularly nice, literal breath of fresh air to escape to.
Personally, I think that if you love Chiang Mai, you’ll also love Hanoi (once you get over the traffic), Ubud, and the Talad Noi neighborhood of Bangkok (which is right around that Leo Self Storage location). But I’ve also met a lot of Chiang Mai fans who are really enthusiastic about Laos, Malaysia, and Cambodia. So, I’d check the historic weather and air quality in all those places for the exact times when you’d be doing border runs, and go wherever it’s most likely to be comfy and affordable.
1) when you’re checking in for your flight in the UK, the airline may check to make sure you have an outbound ticket from Thailand 30 days later, since you won’t be using a visa. So, if you already know where you’re going to after/between Thailand flights, have that ticket confirmation easy to find on your phone. (Or print it out so you can just hand the check-in counter a copy.)
2) If you’re going to be flying in and out of Bangkok, check out LEO Self Storage. Their Chinatown location is near a lot of great cafes and restaurants, and also just a few minutes walk from the train station. LEO offers bag and locker/room storage, but they also have really inexpensive container boxes, about $5 a month, that are about the size of a checked bag, which they store in racks in an air conditioned room. That can wind up being much less expensive (and less stressful) than checking a bag on a round trip flight, and it’s also a great way to free up space in the luggage you *are* carrying, to make room for souvenirs and gifts to take home. Personally, I’m gradually building a box of stuff I can just leave in Thailand year-round instead of carrying it all back and forth on planes. And that makes it feel even more like I’m just coming home when I return to Bangkok. (The staff at LEO is also really nice, and they have some awesome local food advice.)
“What the f*ck is that??? Bob, do you see this thing in this guy’s suitcase? No, no, I don’t give a crap about the heroin. No, no, not the weed either. No, not the strap-on with all the tentacles. No, *that.* Right? Jesus. I know. Are you gonna be ok? Do you need a bucket? Ok? Ok. So, do we, like, have to arrest him for all that other stuff or can we just shoot him right now?”
And that, right there, is why you *never* buy durian coffee in the duty-free and stick it in your carry-on. Customs don’t play.