I'm thinking of a 2-week trip in mid-May (from 7-8th May) around Thailand, flying in from Tokyo. At the moment I'm simply thinking 1 week near Bangkok and 1 week in Chiang Mai , taking the overnight train both ways (or flying on way back).
1) What daytrips, sidetrips or activities do you suggest? Near Bangkok I was thinking of Ayutthaya and Kanchanaburi, and from Chiang Mai, perhaps carrying on towards the golden triangle/Chiang Rai?
2) Is Sukhothai worth a visit? If so, could I hop off there on the way from BKK to Chiang Mai?
3) Will the weather be prohibitively bad in the early rainy season?
4) Instead of Chiang Mai I did have thoughts of taking a return flight to Siem Riep, or a one-way to Hanoi and seeing Hanoi, Halong Bay, Sapa and flying out from Hanoi. I didn't want to be too ambitious though - but at the same time I want to use my resources wisely. (I'm also happy to replan my trip to focus almost entirely on Vietnam/Cambodia, but I chose Thailand as I thought it'd be most friendly to a first-time backpacker. Opinions welcome.)
Budget: ideally about $900 excluding Tokyo-Bangkok flights, but can stretch to about $1300 if it is worth the money. Will pay less for food/souvenirs and pay more for comfort on transport/accommodation.
Timing: I have time/funds for up to 3.5 weeks, but I don't want to overdo myself - I've never visited non-Western countries alone, I'm not sure how much I'd take to backpacker culture, and I'd have another chance to visit SEA again for much longer if I like it this time. If you think I should seize this chance to extend the trip though then please advise.
About me: I'm keen on culture, and love immersive experiences, 'feeling' a country, and seeing how everyday people live, rather than sightseeing at length (I get templed out easily). I'm not much of an outdoor person so not too interested in treks for longer than a daytrip. Not interested in beaches or partying at all.
As it's the first time I've planned a trip like this I would appreciate any advice you may have! Many thanks in advance.
Two weeks in a good amount of time for Bangkok and surrounds and Chiang Mai plus a side trip, but not enough to try and add in Cambodia or Vietnam, unless you extended your trip for the extra week and a half as you mentioned. If you are interested in the overnight sleeper train to Chiang Mai, based on the departure and arrival times of the trains, your best option is to train up to Chiang Mai and fly back. Make your train booking as soon as you can to guarantee the date and time you wish. Also, consider booking the train from Ayutthaya to Chiang Mai. That way you can do a day trip (or an overnight) to Ayutthaya on the way to Chiang Mai.
1. Kanchanaburi and Ayutthaya are solid side trips out of Bangkok, particularly if you catch Ayutthaya on the way to Chiang Mai. There has been a lot of talk lately about Mahachai as a great day trip or quick overnight. Hopefully Tilapia will give you more details on that trip. Pakkret, a small island on the northern edge of Bangkok, is a good day trip too.
As for Chiang Mai, a week will go quickly. Personally, I think the Golden Triangle area is so touristed out now with booths selling cheap tin trays that it isn't worth the effort to get there. If it were my trip, I'd much rather visit Doi Suthep and make an overnight or two side trip to Chiang Dao instead.
2. Sukhothai is definitely worth a visit, but probably not on the two week plan. Sukhothai is often compared to Ayutthaya, with Sukhothia edging out Ayutthaya in terms of charm and quality of ruins. But it is a lot more work to get to Sukhothai, and you'll either need to take the train to Phitsanulok and bus it from there (the overnight sleeper train arrives in the middle of the night - not a good option) , or bus directly from Bangkok to Sukhothai and then bus onwards. You mentioned you like culture, so both Sukhothai and Ayutthaya might be worth it for you, but for most first-time visitors, one or the other is enough - particularly if you plan to visit Siem Reap and Angkor Wat in the future.
3. Usually no.
4. Again, only if you extend your trip, and even then, you are starting to rush yourself. An alternative, if you choose to extend your trip, is to drop down to southern Thailand for a little beach time before you head back. You could also pop over to Nong Khai and explore the Mekong River area for a few days too instead. Since you mentioned you like to feel a country, best to spend more time in one place than rush from one to another.
Budget: Most backpackers spend in the $30 to $35 range per day in Thailand, plus the occassional splurge or two. Flashpackers tend to spend around $50 per day. Your $900 should be fine for two weeks and perhaps even three, depending on what level of comfort you like. Bangkok is much more expensive than even Chiang Mai.
I hope that helps. Have a wonderful time.