Well you can't go too wrong with Bangkok, Chiang Mai and Phuket. women seem to like Chiang Mai and Phuket. Depending on your time, if you are young you can visit a bit with the islands and fry your skin. Or, a little older perhaps take in some side trips to other cities and towns not beach related.
If you start your trip in Bangkok you can purchase your plane rides or other transportation while you are there. For Chiang Mai some tourists like taking the overnight sleeper train to that city. For the sleeper car get the tickets as soon as possible to guarantee a berth. Depending on your available time you might be better off flying to Phuket if that is an interest.
For tours you can get them through local travel agencies. In Bangkok, Pattaya, Chiang Mai and Phuket there are many travel agencies available to book tours for you. They will have a list of popular tours to choose from. You will be picked up at your hotel and returned to your hotel at the end of the excursion.
You have to plan a budget and see how much you can afford for hotels and everything else after you pay for your plane ticket. When you know how much you can afford for your hotel then you can ask for suggestions that fit your budget. Many young travelers head for Khao San Road area and others head for areas like Sukhumvit Road where you can also use the Skytrain.
If you intend to use debit or credit cards you must first notify the banks that you will be overseas. If you don't tell your banks your ATM withdrawals may be denied. The fee to use an ATM in Thailand is 150 baht so when you make ATM withdrawals take out the maximum you can at one time. You don't want to have a lot of fees for small withdrawals.
Thailand is one of the best countries in Asia for cashing travelers checks. The fee to cash a travelers check is 33 baht per check so only bring the largest denominations you can get. You don't want to waste a lot of fees on small value travelers checks. Compared to the fee to use an ATM for the same amount of money a travelers check is a good value.
At the airport there are bank money changers available all the time. Wait until you get to Thailand to change any money over to Thai baht for the best rate. Only bring larger size currency to cut down on bulk. Make sure your currency is not dirty or older series.
Limit the amount of valuable items you bring with you on your trip. Sometimes it is your fellow travelers who rip you off in hotels not the hotel workers. How long will you be in Thailand? How long you can stay in Thailand and even if you need a visa or or not depends on the passport you will be using. Check your visa requirements.
If you stay in hotels that have safety boxes ((and use them)) you lessen your chance of having something stolen. Don't trust anyone who you don't know from back home! If you meet up with friends who use dope you may also get busted along with them. Many dopers store their dope in their friends bags and they take the fall when caught. There are women in Thai jails right now because of their boyfriend's dope!
Good luck.
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