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Cactusfriend,
You're welcome. And yes you're right, 'take the plunge and go for it!' is the best attitude to have. Once you're over here keep an open-mind and be adaptable with your plans. You may end up in one place that you really like and want to stay longer than intended. It is quite easy to book train/bus/air tickets as you go along.
With 3 weeks, there is so much you can do it all depends on how much you want to cram in or how chilled out you want to be. I get asked the question about itineraries quite a lot. Much depends on the individual, but here's a suggestion:
Spend 3 days in Bangkok and have a bit of a chance to get over the flight. Bangkok can be overwhelming from the very first time you enter the arrivals hall and are greeted by cries of 'Taxi! Taxi!' 'Taxi Madam, Where you want to go?' Some people love Bangkok, some people hate it. Few people are indifferent. The Grand Palace and Wat Po are recommended as is a trip to the Floating Market at Damnoen Saduak. If you do an organized tour to the Floating Market, it will probably include a stop on the way back at the Rose Country Garden Resort. There is a display of cultural dancing and an elephant show. Geared at tourists, but hey, we're all tourists whatever we might think, and it's enjoyable enough. Not what many people would call the 'real' Thailand but a pleasant introduction for the first time visitor. The Grand Palace can be done as an organized tour or if you're a bit more adventurous it is easy enough to get to by taking a boat along the river (a pleasant trip by itself). As you've probably read, there are various scams operated by tuk-tuk drivers and their friends who will tell you 'Grand Palace closed today'. Ignore them and carry on.
From Bangkok, head north to Chiang Mai for 7-10 days. Many people find the easy-going atmosphere a relief after Bangkok. Even on rainy days there is plenty to do and it is easy to get around by public transport. You're bound to meet lots of friendly travellers and locals who can help you out getting your bearings. Plenty of temples, great food and cheap prices. If shopping is your thing there is the famous Night Bazaar, but the weekend Walking Street market is much better. There are 2 excellent modern malls and the trendy Nimmanhaemin Road in the west of the city is home to a number of funky boutiques and has a relaxed cafe culture. There are plenty of half-day trips and day trips ( I recommend the temple of Wat Phra That Doi Suthep and the National Park at Doi Inthanon). The city is full of travel agents who can book any trip for you and most hotels and guest houses can also arrange for you. After a day sightseeing, relax with a traditional Thai massage. On rainy days, book yourself into one of the many spas dotted around the city or chill out in a restaurant and chat with the locals. Just enjoy yourself!
From Chiang Mai head south for a week on a beach. Bangkok Airways run direct flights to Ko Samui from Chiang Mai. Alternatively, Ko Chang or Krabi could be a good choice. Ao Nang is a good base if you are going to Krabi. It gets criticized for being too commercial, but it has a lot going for it and as I say, is a good base without being stuck in one place. You could visit a different beach or island everyday and there is plenty to do if you fancy a day away from the beaches or the weather is bad.
The above is just a suggestion. Many people will suggest other places: Ko Lanta, Phi Phi, Ko Samet, Pai, Chiang Rai . . . a whole host of places. Everybody has their favourites and all places have their good points and their bad points. But the above itinerary gives you a bit of everything; a few days in the capital city, a week or so in the mountains of the north and a week or so on the beach. They're also all quite easy to travel between (particularly by air). Ultimately, read as much as you can (not just Lonely Planet!) and listen to as many views as you want. Go with your gut instinct because only you can know what it is you really want out of your trip. Best tip - be flexible and be prepared to change your plans. It's easy to arrive in a place and be totally captivated and want to stay longer (or completely disappointed and want to move on!)
Talk with the locals and try and retain a sense of humour even when you're hot and bothered (or soaking wet from a sudden downpour). Enjoy yourself and be relaxed and I'm sure you'll have a great time.
Thaizer.
Thailand tips, advice & information