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Travel solo if you haven't already tried. It is an amazing experience to put yourself out of your comfort zone. Do keep that in mind to stay street smart. Be cautious of scams in SEA. Whether you are a Caucasian or Asian, they can tell that you are a tourist, and many will try to rip you off. A boat ride that costs $5 for local, they would try to charge you $100 for it. Also, understand the corruption level of authorities on the countries you visit and act accordingly. In Thailand, the cop will catch you to ticket you for anything they can find, just because you are a tourist. In Philippine, many cops will be the one kidnapping/killing you for ransom, or if any altercation occurs between you and local, they will always side with locals no matter what and later demand a ton of money as a bribe to be released from jail. In Indonesia, some tourists area have tourist dedicated cops to help you with. If the cops in Thailand catches you to fine you, never get angry and more often than not, just pay small bribery that they demand as it is not worth the trouble. In Philippine, avoid any contact with cops and try to resolve the matter without cops getting involved else it will get very expensive. In a case where cop's involvement is absolutely necessary, call embassy to let them know where you are and do make sure that cops know that you have contacted your embassy. In Indonesia, tourist cops are usually safe and will try to help you in case of altercation with locals.
If you are planning on activities like river rafting, sandals, if not, flip flop was enough for me. Avoid cotton t-shirts. It is so hot and humid, you will need to take shower multiple times in a day. On a hot day in Phuket, without air condition, I was sweating as I was coming out of shower trying to dry myself.
Do all your foreign exchanges in Singapore airport if you are planning on visiting Singapore as beginning of your trip. Buy Starhub simcard from airport with roaming for $15 Sing$($13.50 CAD) to get 2gb of roaming data for 30 days. Can't get cheaper than that! Download Grab taxi(SEA version of Uber) to avoid taxi scam.
If you have Aeroplan points, there are ways where you can set up a "mini round the world trip" for cost of a single trip. Go read ton of articles on flyertalk forum. I used this and flew all business class multi-city trip for 150,000 points. By the way, avoid Air Canada and fly Asian based as they don't charge you extra taxes and provide much better services.
Most locals are extremely friendly and kind, but ones that are fluent in English, be cautious. As someone suggested above, buy travel insurance and make sure that you understand terms and conditions as some insurance will not cover you unless you contact insurance in case of emergency prior to expenses.
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