Living in Singapore
Scholars will be assigned to live in a hostel/boarding school (not always) nearest to your school. This will be where you will sleep, eat, do your homework, have tons of sleepovers (just kidding. your hostel mistress will probably scream down your throat if you do that...only if she finds out) and have loads of fun with your other scholar friends.
As with schools, hostel experiences will differ from hostel to hostel. Typically, secondary school scholars will live in two hostels throughout their studies here in Singapore (one for secondary school, one for JC). But for me, I only lived in one, because both my schools had their scholars staying in the same place! Sad to say, I can't really offer much insight into the differences of hostels, but I will try.
Most hostels have curfew for scholars. Some are stricter than others. For example, Oldham Hall requires their boarders back by 6pm every Sunday; Hwa Chong Boarding School locks their gates at 10:30pm sharp and you would have to cry and beg the guard to let you in. Some hostels have nicer facilities than others. Boarders at ACS(I)'s boarding school can use the school's swimming pool, gym, squash courts, track, everything. Plus they have an inbuilt laundry center that is dedicated to washing and ironing their clothes. Some hostels have no facilities. Sad. Some hostels have good food, some have absolutely terrible food. It is common to find a worm or two pretending to be rice grains at some hostels. Believe me, it's more disturbing than it sounds. The list goes on. Some are even nicknamed Parry Hell (orignially Parry Hall) due to the hellish experiences you go through there. Of course, there are also people who love Parry Hall to bits! Unfortunately, or fortunately as some may see it, Parry Hall has closed down.
Most boarding schools are co-ed, with single sex dormitories. Some like Nanyang Girls' Boarding School, accept only, well, girls. Some have attached bathrooms, most have communal toilets. Some are air-conned, some are not. Sometimes you get 8 to a room, sometimes you get 2 to a room. It all depends. At my boarding school, the higher level you are, the more privacy you get - e.g. less roommates. Some like Oldham hall have compulsory Chapel worship for all boarders as they are affiliated to the Methodist Church, most are secular.
All in all, no matter where you land up in, keep an open mind and you'll definitely enjoy yourself as long as you don't expect royal treatment!
For a comprehensive list of which schools stay at which hostel, visit this very helpful ReCom Wiki Page.
It is a little outdated, but just a little. For example, there is a new Anderson JC Hostel that will house their own scholars as well as absorb scholars from Parry Hall and more. Also, Anglo-Chinese's Boarding School will be co-ed, absorbing their female scholars into their new hostel building starting 2012.
On weekdays, you will be provided with breakfast and dinner by your hostel (and maybe even supper, depending on where you land up). Lunch is usually eaten in school because most school hours extend past lunchtime. Hostels usually provide lunch on weekends.
The quality of food varies from hostel to hostel, as with all other things. In my six years at my hostel, I have eaten food from four different caterers! Usually new caterers serve up yumz food for the first month or two, and then the quality goes downhill afterward. Vegetarian and Halal food is also catered for at my hostel - though I always pity them because they eat the same food (curry curry curry) every single day. Sucks to be them at my hostel. My hostel had set menus for the week (e.g. Monday = Nasi Lemak day; Tuesday = Chinese food day; Wednesday = Western food day; Thursday = Chinese Food day; Friday = Healthy eating day) so things can get a little boring because your food choice will be repetitive in nature. Eating in however, is an excellent way to save money, because buying anything in Singapore is generally quite expensive - especially if you can't kick the "let me convert it to Ringgit first" habit.
There are thousands of choices for you if you choose to eat out. Hawker centers are at every street corner (not literally, but they are common); fast food restaurants are everywhere; normal restaurants are everywhere too. Just within a 4km radius from my hostel alone, I could find: McDonalds, KFC, Pizza Hut; Canadian Pizza; Dominoes Pizza; Ice-cream shop; cheap and good Thai restaurant; french restaurant; italian pizzeria; Penang restaurant; Hong Kong restaurant; Cold Storage; Fairprice (Singapore's most widespread supermarket); two petrol kiosks (to satisfy my instant noodles and random Paddlepop rainbow ice-cream cravings); 7-11; bakeries; excellent prata (roti canai) stall; cheap and good western cuisine AND SO MUCH MORE. I think I've made my point.
But if you don't control your cravings, you'll definitely be burning a big hole in your pocket!! Of course, there are the S$2 double cheeseburgers at Macs. Though, if you don't control that craving, you'll be burning holes in your shirts to fit into them!
Singapore's famed transport system will actually serve you much convenience during your time in Singapore. The two main public transport are the bus and the MRT (Mass Rapid Transit).
Most people in Singapore have a neat little stored-value transport card called the EZ-link card. (Though I think it is now called Cepas or something, but everybody says EZ-Link - pronounced ee-zee-link or iz-link) Basically, it works as a prepaid transport card. You store in money. When taking the MRT or bus, you "tap in" to one of the card readers at the entrance. When you alight, you "tap out" and your bus fare will automatically be deducted from your card.
As a student, you will be using a student EZ-link card. With this card, you pay much much much cheaper fares on public transportation. I personally felt the pinch of non-student fares when I recently went back. The maximum fare on the normal EZ-link is S$1.96, while for a student, the fare is capped at a maximum of S$0.58.
Cabs are also everywhere in Singapore. So if you find yourself lost and stranded at midnight, a perfectly safe mode of transport is just a phone call or a hand wave away. Cab fares have increased tremendously however, and I try to avoid taking a cab unless it is absolutely necessary. A recent taxi ride of mine set me back S$35. No doubt it was during peak hour (more expensive meter) and there was a huge jam, but still, ouch.
Life in General
Singapore is the heart and hub of Southeast Asia. If you're willing to get yourself out there, there will always be something happening in some part of town.
The shopping is great, if you're into that. Orchard road alone has Far East Plaza, DFS, Tangs, ION, Wisma Atria, Lucky Plaza, Plaza Singapura, Heeran, Paragon, Somerset 313, The Grand Cathay, *scape (no, there's no footnote at the end. It's just spelled this way), Cineleisure, and a few others that escape my memory. And that's just ONE road alone, albeit the most shopping road any shopping road can get, but still one road. What's more, there is a mall in every area of Singapore! You have Lot 10 at Chua Chu Kang in the West to Heartland Mall at Kovan in the middle to Parkway Parade at Marine Parade in the East. You have Bukit Timah Plaza in Bukit Timah, Bukit Panjang Plaza in Bukit Panjang, Yew Tee Point in Yew Tee, Clementi Mall in Clementi - you get the idea.
The arts scene is getting better. Broadway musicals make their pit stop in Southeast Asia in Singapore. Since I've been here, there has been Phantom of the Opera, Wicked, Lion King, We Will Rock You, Avenue Q and more. Artistes also like to hold concerts here in Singapore. Be it your favourite K-pop band or american heartthrob, if they want to hold a concert in Southeast Asia, chances are it will be held in Singapore. I've personally queued up for ten hours to get a handshake and autograph from Taiwanese boyband Fahrenheit (I was 14 and young, and had a lot of time). Some of the artistes that have held concerts here in recent years (i.e. in the past 3 years) include: Super Junior, Coldplay, Muse, Janet Jackson, heavy metal band Iron Maiden, Justin Bieber, Avril Lavigne, SHINee, SNSD (Girls' Generation), Paramore, Westlife, Amy Winehouse, Show Luo, JJ Lin, Stephanie Sun, Disney on Ice, Death Cab for Cutie, and so so so much more, I can't even name them all without going mad. If you're more into classical arts - orchestra, ballet, choir, dance, drama, plays - you will have your fair share of performances as well. Every other night, there will be an orchestra performing, or a school ensemble playing, or a local comedy going on in some concert hall in Singapore. You have the Royal Ballet companies coming in to dance Swan Lake, or the Vienna Choir Boys coming to croon some carols into your heart. And the best part of it all - you get to enjoy special student rates!! Very good deals for good seats. My one regret throughout my six years in Singapore was not to make more use of this advantage. Now I can't anymore. :(
Night life is very happening too. But chances are, you're not of legal age yet. So I won't elaborate. Heh. You shouldn't be staying out till wee hours in the morning anyway, you have boarding school curfew!
One thing lacking in my opinion, would be the sports scene here. Outside of school, there's not much hype about sports. Admittedly, they are trying to promote it, but it just doesn't seem to be taking off. Even in school, if you're not a school athlete, the only sports you'd probably be thinking about is your yearly Physical Fitness Test (PFT/ NAPFA).
If you want a weekend to just chill out - there's Botanic Gardens or the various parks scattered around Singapore. There's East Coast Park; there's West Coast Park and lots of other parks in between. If you're a book person, national libraries are found almost everywhere too! And they are pretty well stocked.
Essentially, there's something for everyone in Singapore if you're willing to find it! ;)