@Iris **********

Hmm, you are a high-end tourist with a lot of money, so do a trip that reflects that. Phuket is a must on your list. And also I would consider smaller less crowded island (since you have money), instead of the tourist polluted Samui, etc.

You can rent a motorbike for $100 CAD for 1 month in CM.

By the way, in Chiang Mai, there are very few taxis, but many Tuk Tuk and even better, songthaew, which are very cheap. Can bring you from Nimman to Old City for $1 each. Chiang Mai is convenient because it is VERY easy to get around. It's not overly crowded or insane traffic jams. A lot of people drive motorbikes. Also, Chiang Mai can be up to 50% cheaper (cost of living) then Bangkok, Samui, Phuket, etc.

Old City = the square you will see on the map if you google Chiang Mai. It's a backpacker heaven but for elderly, you might be too old for this. Nimman is more layback, with lots of coffee and foreigners love to go there to work from coffee shops. Old City also has everything and you will want to walk there and visit temple, markets, coffee shops, etc (a few KM from nimman), but the quality of tourist is lessen so Nimman is where you want to end each day at, sleep there, morning breakfast, and then decide each day where to walk.

No, I've lived in Isan (Khon San), since the pandemic. I was in Chiang Mai for a few years before Covid. For Chiang Mai, you probably want to book around Nimman (not Old City, you are too old for this) and go from there. Any small street in Nimman or alley are good options. From there you can go all around Chiang Mai City center for a week or two and then go upper north to Chiang Rai, Pai, etc, and do some activities, temple visit, Tea plantation, etc.

You need to check which place fits you best. You got a lot of advice to avoid Hua Hin... but imo it's a great place for elderly. Many people retired there. If you want to relax and be at a slow pace, it's unavoidable imo. People are giving you advice based on their own lifestyle rather than your own. Just be mindful of that. Chiang Mai, Phuket, Hua Hin, and some beach in between.

Thailand is separated into 4 (in my opinion). The Chiang Mai area North-West, Isan North-East, Bangkok middle, and South Thailand. You will have drastically different experiences in all 4 places. Isan is the countryside, not really for tourists. It would be like going to Saskatchewan. I would start fresh in Chiang Mai for a week, then go Chiang Rai, Pai, etc. Then fly to Phuket, then go from there (decide which island to go next). You do not need to see Bangkok or Pattaya.

Beach? Nature? Mountain? Chiang Mai has a ton of historic sites, coffee shops, and markets. The one thing that Chiang Mai does not have is the beaches. But if you are into nature, mountains, temples, CM is great. You can take a trip upper north to Chiang Rai, Pai, etc, and visit Tea plantations and more.

It depends on what you are looking for. Chiang Mai doesn't have beaches, it's near mountains and it's cold during December and January (can be +10-15 morning and night, +25 afternoon. For me, also a Canadian, it's obv great, can't complain, lol. Hua Hin is also laid back and has beaches. Bangkok is loud, traffic, smelly, air is bad, temperature too hot, etc. For elderly, it's overwhelming. I'm also from Canada, 36, and I've been living in Thailand for 10 years. Bangkok will shock you, and not in a good way. I live there for a year, and I've lived in Chiang Mai for two. As for booking in advance, if you are looking for comfort and expensive hotel, yes, but if you don't mind guesthouse, etc, you don't need to. Thailand guesthouse and hotel selection are massive everywhere you mentioned above. And as for Kuala Lumpur, same as Bangkok, but a lot more tolerable. I had a lot of fun in Borneo.

@Lindsay *****

Brian is being disingenuous. The chance of getting in trouble for 3-day overstays is 0.0001%. It's a risk but a tiny one. I'm not arguing with explaining the potential consequences of taking such a risk but exaggerating the likelihood of it is disingenuous. Brian should have included the likelihood of getting into such trouble rather then just scaring you with the potential consequences.