Disclaimer: I like disclaimers before the meat of a post. The other disclaimer is that I have been planning this trip compulsively for the last eight months. I've been planning it off and on for the last seven years, but that's neither here nor there. Compulsively. Eight months. Now it's to a state where I need to bounce these ideas off some locals or expats.

Over Christmas/New Years we're going on our first real holiday in years and by far our biggest yet. This involves a lot of premium cabins and a certain amount of family time, but it also involves six days in Singapore (realistically more like 5.5, but I broke it into calendar days). I have put together a preliminary itinerary, as people do all the time here, and I was hoping that someone could give it a once-over and point out any glaring omissions or mistakes, or fill in the blanks with blatant personal bias. Any of those is okay.

Day 1: New Years' Eve: Arrival, Hotel, NYE Fireworks.

This is the "Arrival" day. Honestly, we have very little in terms of plans. We're staying in Chinatown right by Outram Park MRT and arriving roughly 3PM so we won't have the day to sight-see. I was expecting to go directly from the airport to the hotel to Boat Quay/Clarke Quay, do a quick pass, and hopefully end up at the Singapore Food Trail for dinner. We're open to suggestions. If there's a good restaurant or place around with a good view of the fireworks, I'm interested. Price is a factor, but not as bad as "I want to spend $1 for a beer". I just don't want to spend $200 for dinner just so I can see fireworks and sit in a fancy restaurant. As you will gather if you read on, we're none too concerned about fancy restaurants. Or can we reasonably expect to even be able to find a place on the day?

I'm also open to a suggestion of a good microbrewery or brewpub that won't be crazy busy. Busy is fine, though. A good off-license in Chinatown is also a welcome suggestion for the rest of the trip.

Day 2: Wed, 1 Jan: Chinatown, Bras Basah, Marina Bay

This is the "tourist" day. Not planning to over-indulge on NYE and possibly (correction, intending to be) still jet-lagged from westbound travel, we'll probably be up early-ish. The plan today is to see the areas in and around the CBD with a few optional museum stops in each main area. This day could be interchanged with Day 3, but we thought Ubin would be quieter on the 2nd.

Coffee: Oriole Coffee Roasters, Jiak Chaun Road. If it's good, it will be the start of most days, probably.
Breakfast: Ya Kun Kaya Toast in Chinatown.
Morning Activity: Chinatown. We're planning to walk into Chinatown, see the markets, maybe do some shopping, Bhudda's Tooth temple, see the big stuff. Budgeting 2-3 hours here until early lunch. We'll be staying here, so it's not necessary to spend lots of time and see it all, we have evenings for that.
Lunch: Maxwell Rd. Hawker Center.
Afternnoon Activity #1: Bras Basah/Fort Canning. If we play our cards right, we'll be good to walk up to Fort Canning first. In theory, this will involve not doing Clarke/Boat Quay, as we'll have seen it before or will see it after anyway. After Fort Canning we'll head down to Bras Basah and Dhoby Ghaut, possibly stopping at the Peranakan Museum or National Museum, depending on our motivation level. We'll probably do a quick run up Orchard Rd as well, but knowing MrsBarn's shopping habits I suspect she'd be much more interested in a smaller area. Again, budgeting 2-3 hours before first dinner
Lunch #2: Bras Basah Complex Food Court (EDIT: OR Chin Chin Eating House)
Afternoon Activity #2: Esplanade, Mandarin Oriental Hotel area, whatever you call that point just across from the Marina Bay. This is going to be a late afternoon sort of thing, so not sure if we want to take 2-3 hours and stop at the Gardens by the Bay now or not. The alternative, of course, is to do this before Bras Basah/Fort Canning, or to skip Fort Canning altogether and spend a bit more time down here. Possibly stop and see the Marina Bay City Gallery (keeping in mind I'm a huge nerd and a museum about anything public works project-y would be awesome).
Activity: Return to hotel, regroup, head out for Dinner #1.
Dinner #1: (EDIT: Keong Saik Rd instead of Chinatown Night Market)
Evening: Night markets, maybe meet up with friends. Keeping a few slots for this depending on when they have free time (they have kids and jobs, we're on holidays and our kid will be in Canada. Scheduling is at their discretion). EDIT: If not, considering a bar like 1-altitude or LeVel33, just to get a view of the city like you'd get from the flyer, but with beer.

Day 3: Thu. 2 Jan: Ubin, Changi Village, Exhaustion?

This will be our "nature" day. The plan therefore revolves around Ubin, getting there and away, and seeing some east coast sights. I originally also had Kampong Buangkok on here, but couldn't decide if that was a bit too ambitious, so it sort of got dropped and I pushed up the board game cafe to here because it's low-physical-energy.

Coffee: Coffee in the hotel before we go. Too early for Oriole I suspect.
Breakfast: Not sure about this one. We're going to try and get an early start to Ubin, but we'll likely be taking the MRT/SMBS out. From what I see, it's more or less the same to transfer at Simei, Tampines, or Pasir Ris, with direct buses from each. I'm leaning toward Tampines and then just having breakfast at Tampines 1, but maybe there's something way better near one of the others? Or is taking the MRT eastbound at 8:30 AM ridiculous busy and we should cab it instead? Or, am I making a huge mistake and we should do Changi Village for breakfast? We can do that. Never had Nasi Lemak. Want to.
Morning Activity: Ubin. Probably renting some bikes, heading out to Chek Jawa, doing the island thing.
Lunch: No idea. I assume our options on Ubin are going to be limited, so I figure we'd just hit whatever's by the jetty, unless there's something I haven't seen yet. Suggestions? Would it be a better option to get something packed to go from Changi Village Centre? We can do that.
Afternoon Activity #1: More Ubin, unless we've seen it all. Then back across to:
Dinner #1: Changi Village Hawker Centre. Unless it’s closed or not good for dinner.
Activity: This is going to be pretty dependent on how we feel. On one hand, we're out at the east coast and I'd think it'd be good to see the park just a bit. On the other hand, I suspect we could be pretty tired, so this might consist of just heading back to the hotel for a few hours. But if I'm missing something interesting out here, please let me know. The other option is to head back to the hotel, regroup, clean up, and hit up a board game cafe. We'll leave it flexible.
Dinner #2: Very dependent on how we're feeling, maybe Chinatown Centre or Tiong Bahru? Lau Pa Sat?
Evening: Likely exhaustion. Probably hotel pool. Certainly beers on the terrace at some point. This might also be a good day to meet up with our friends in town. Unsure.

Day 4: Fri 3 Jan: Food, Food, Geylang, Food

Today is the "food" day. All those days before? Those were not the food day. They were only practise for the food day. Today is the day I've booked a Singaporean Cuisine class with Ruqxana at Cookery Magic that I will also promote here, because if anyone wants to attend you are more than welcome. The rest of the day will be... more food. This is also the morning where we find a nice few-hour spa treatment for MrsBarn around Outram Park. Spa suggestions around Chinatown/Outram Park are very welcome. Assume, also, that I will be doing the first half of this itinerary alone.

Coffee: Either hotel coffee or Oriole.
Morning Activity #1: Tekka Market. I love markets. I love wet markets. I've never actually been to a proper Asian wet market, but I already know I'm going to love it. The only Mandarin I know was learnt in and directly related to a market, so this should be telling. I don't even know what I want to buy, just that this is a great time to see it.
Breakfast #1: Something at Tekka, of course.
Morning Activity #2: It's a toss-up between Fengshan Food Center or Whampoa Wet Market. Fengshan is closer to where I need to be at 11, but a cab is not out of the question. I may just do a cab anyway.
Breakfast #2: Wherever I end up between the two of the above.
Morning Activity #3: Cooking Class! I suspect this will also involve lunch. 3 hours at least for this, bringing us probably up to 14:30
After this, the plan is to meet up at Paya Lebar or Eunos MRT (or at the class itself) and go down for....
Dinner #1 and #2: at 328 Katong Laksa and Tian Tian at Joo Chiat respectively. Tian Tian is optional, since we may get it at Maxwell Road Centre, but in case we have to pass (huge line) we can go here. Also, we're right there.
Afternoon Activity #1: Broswe Joo Chiat and head up to Geylang. Not sure what to do here, but I suspect beer will be involved, shopping will be involved, and looking will be involved. If there’s a good Durian place, I would go. Never had it, not sure I’ll like it, but I’ll definitely try it.
Dinner #3: Back to Old Airport Road Food Centre.
Afternoon Activity #2: Bugis/Kampong Glam
Evening Activity #1: Attempt to return to hotel. Lie down and moan. Regret eating so much.
Evening Activity #2: If at all possible, we'll go out. If that's too much effort, we'll have a beer in the hotel.

Day 5: Sat. 4 Jan: Tiong Bahru, Treetop Walk/Henderson Waves, Options, Little India.

This is the "flexible" day. We're still going to have lots to see, but I want to maximize it without being too touristy like Day 2. We also can move things between this and day 6 if they fit better that way. If there's a morning to relax a bit around the hotel, this is also probably it. Alternatively, we could sleep in on day 6 and instead do the Botanical Gardens/Adam Road Food Centre for breakfast.

Breakfast: Tiong Bahru Food Centre.
Activity: There's a historic walking tour of Tiong Bahru we could take, but I'm tempted to instead head out from here to the Treetop Walk and down through Henderson Waves. Unless someone's done the tour and can vouch that it's really good? Then hop the cablecar down from Faber to Harbourfront and CC line over to:
Lunch: Pasir Pajang Food Centre. I hear good things about the seafood and since we're already basically there then I figured why not? Seafood!

For much of the rest of the trip, I've sort of put together a list of things on the west side that would be interesting, but if we missed we would not be regretting later. I have some ideas of how to organize it, though, but would love suggestions.
Early Afternoon Activity Option #1: Singapore Zoo, followed by Chomp Chomp Food Centre
Early Afternoon Activity Option #2: Japanese Garden/Bird park (although as my SG friend says: "really, it's just birds")
Early Afternoon Activity Option #3: Walking around Bukit Timah Nature Reserve.
Early Afternoon Activity Option #4: Sungei Road Thieves Market and Kampong Glam
I suspect any of those options will take the majority of the afternoon, although I'm leaning a bit toward the zoo. I'm also open to suggestions
Late Afternoon Activity: Little India. This was originally on day 6, but then I thought it would be better if we had a late afternoon/early evening here, rather than try to fit it in on the last day when we may prefer even more flexibility.
Dinner #1: Tekka Centre, probably.
Early Evening Activity: Mustafa Centre. Either we'll love it, we'll get bored and leave in ten minutes, or we'll get lost and never return. We'll have a story no matter what.
Dinner #2: EDIT: Decided we might give Bismillah Biryani a try. It's in the neighbourhood and I believe this itinerary is low on Indian food.
Evening: Back to the hotel, think about packing.


Day 6: Sun. 5 Jan: Botanical Gardens, ???, Changi, Departure.

This is Departure Day, but our booked flight leaves at 1 AM the next morning. So we have the full day, but I'm unsure of how we'll be for late check-out and we should be back at the hotel just after Dinner #1 to get the MRT to the airport.

Coffee: Yes. Very. Want to get up early.
Morning Activity #1: Botanic Gardens
Breakfast: Adam Road Food Center
Morning Activity Option #1: Gardens by the Bay, if we have not yet seen it.
Morning Activity Option #2: Singapore Zoo + Chomp Chomp Food Centre
Morning Activity Option #3: Maybe dim sum with friends? Depends on their schedule.
Morning Activity Option #4: Return to hotel, Pool.
Activity: Check out of hotel around noon, leave bags.
Lunch: Chinatown Food Center.
Afternoon Activity Option #1: Sungei Road Thieves Market and Kampong Glam if we haven’t seen it yet, otherwise
Afternoon Activity Option #2: One of the options we have not yet tried.
Dinner #1: Revisit whatever Food Centre we liked most.
Late Afternoon Activity: Go back to hotel, get bags, MRT to Changi. Check in.
Dinner #2: Something light at SKL T2 or find the Airport Food Centre.
Evening: Last-minute shopping at Changi. SKL. Ride the Slide @ T3.
Departure…. and BTC on SQ, of course

So believe it or not that's only iteration 2 or 3 of this plan. I would love some suggestions, though. If I missed something, let me know. We've got a few months left and I have more or less free reign to plan.