WHAT TO BRING?
The first thing you will need is a passport that will not expire within 6 months of departure. You can get your passport renewed at the Post Office and can get it within 10 days if you pay extra for expedited process. Americans are not required to get a visa but if you want to stay longer than 3 weeks, you should check out getting a 30 or 60 day visa at the Thai Embassy. Always remember to make a color copy of your passport in case in gets lost or stolen.
As far as packing clothes and your flight, there is nothing that compares to Strikeeagle's "Air Traveler and Layover Survival Guide"...it covers everything. I like to travel much lighter but some people like to have everything and you might be one of those people. The main thing that you want to pack are large boxes of Durex Ultra Thin Condoms. You may buy other brands but do not buy local Thai condoms as they are designed for smaller units. Do no carry on Viagara(unless prescribed) or illicit drugs...prison life in Thailand is no picnic.
WHEN TO GO?
This is somewhat subjective also. The high season is November through February. I try to avoid those months because every monger in the world is in Bangkok and the bars are packed to the rim. The girls will ask for more money during high season and many of the mongers are there on "business" and have no clue what the current rates are. If there are a plethora of mongers, the girl can ask for outrageous prices and not flinch because someone will pay that, especially to the hotties. March through June are hot months but the monger traffic is reasonable and the new girls usually start around this time. July through October is monsoon season but the bars are packed with tons of girls and very few mongers during September and October. I would say the best month to go is any month but May and October are particularly good.
LEARNING THAI?
First time visitors might not want to learn Thai but most mongers return again and again and learning Thai might be something they should learn, especially if they have a Thai girlfriend. If you live in Los Angeles, the Wat Thai has Thai classes on Sunday in North Hollywood. If you live near a Thai or Lao Wat, call to see if they offer any courses or individual instruction which is usually free. You can also order many books online or buy them at Borders. You should order books with tapes or CD's. "Thai For Beginners" is a good start. You might want to get some of the beginner tapes and place them in your car during rush hour to at least learn several key phrases and learn about Thai culture. I also recommend buying the series by AUA in Bangkok: Take the Sky Train to Ratchadamri station and take the exit on the Regent Hotel side and walk about 200 feet to the AUA school and buy directly from the book store for about 250 baht each book. Bookazine in Bangkok has several excellent tape/book series also.
TRAVEL GUIDES:
The best guides for Thai tourism are Lonely Planet and Moon Series. They will help plug in the holes regarding tourist destinations and other trips outside of Bangkok.
WEB SITES:
The best web sites(other than Hombre) for learning additional mongering information can be found at:
Dexterhorn.com
Pattayaplaza.com
Stickmanbangkok.com
Nanapong.com
Nanaplaza.com
MONEY:
Thailand is extremely convenient with regards to money. You can use your ATM card freely but realize that many banks in the U.S. will hit you for fees up to $4 per transaction which can be a lot in the long run. The best rates are with Traveler's Checks and you can get them replaced if lost or stolen. Always good to have some traveler's checks in case your ATM doesn't work or you lose it. You should also bring some emergency cash in case you lose your traveler's checks and ATM Card. It is also adviseable to bring an extra ATM Card or Credit Card and hide it somewhere in your luggage. Remeber to make copies of your Traveler's Check receipts and do not keep your receipts with your checks. The exchange rate fluctuates from 41 to 43 baht to one dollar. Banks are the best place to exchange money but most banks have kiosks all around Bangkok for convenience. The airport's rates are competitive with any bank in town.
You should consider buying a money belt or one that goes around your neck during transport to Bangkok and in between cities. Always keep all of your belongings in the hotel's safety deposit box. You will be charged heavily if you lose the key so I like to leave my box key in a safe place or at the front desk if you have developed trust with the hotel.