Indonesia vs Philippines for holidays in December
#1
I'm trying to decide where to go for vacation at the end of December. I am based in Tokyo (but I'm European) and will be off work from Dec 20th til Jan 5th.

I'm thinking of going either to Indonesia or Philippines. If I go to Indonesia I would fly to Jakarta and travel around, probably in Java, but I was thinking of checking out some islands in the East like Nusa Tenggara. If I go to Philippines I would fly to Cebu and traveled around maybe to Iloilo. 

Is there any reason to prefer Indonesia or Philippines at the end of December? Do you have any other travel tips?
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#2
I think it depends really on what your objective for the trip is. If you're there just to rack up notches I'd suggest the Philippines. If you're looking for more diverse and I guess culturally interesting trip, I'd vote for travel in Indonesia. Not that Indonesia is hard to secure notches, but outside Jakarta its a lot more conservative.
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#3
It's worth considering that December will be around the peak of the rainy season in Indonesia.

We're not talking a continuous downpour / monsoon, but there will be heavy rains probably on a daily basis for a couple hours in many parts of the country.
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#4
Philippines is obsessed with Christmas, I mean obsessed. They start in like September. This cuts both ways. It is an interesting and exciting time to visit, and the energy is intoxicating.  However, it does disrupt routines, particularly in that period between xmas and new years. Will definitely be harder to meet girls in the typical ways, but it can still be done. However, if you meet one girl (or one you have met online) she would almost certainly invite you to her family events. This would undoubtedly be an amazing cultural experience. Filipinas know how to party!

In Indonesia things would be pretty much business as usual. Some Christmas celebrations maybe, but being a Muslim country not nearly as much. Bali over the holidays is fun.
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#5
Further to the responses already, I'd like to stress the Christmas factor - it's a big thing in the Phils but a minor event in Indonesia.
So if gaming girls is your focus, then you could get cock-blocked by Christmas (oh boy, that sounds soooo blasphemous).

But it sounds like you are doing this for exploration and vacation purposes as opposed to pumping pussy. In which case both countries have their benefits. But be mindful about spending too much time at airports and in transit. For example, ask yourself why you are thinking about Nusa Tenggara? It is the beaches? Natural beauty? You may be able to get the same/better in other parts of Indo much closer to Jakarta (eg. you can go snorkelling 90mins boat ride away from Jakarta at Pulau Macan). Yogyakarta is pretty awesome for history and culture and there are a couple of volcanoes nearby too.

Logistically, the Phils is closer to Tokyo than Jakarta; economically, the costs are similar; gaming wise, both are pussy paradises; food wise, I prefer Indonesia; language wise, Phils speaks English, but it's never been a problem for me in Indo and I speak no Bahasa.
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#6
The purpose of this trip is to meet girls and and to get the vibe of places I have never been to. I will do some touristy stuff, but not too much of it. It would be ideal if I can meet random folks on CouchSurfing and do touristy stuff with them.

Yes, I was concerned about the effect Xmas will have on gaming, and you seem to confirm my suspicions. I didn't know about the rain in Indonesia. It seems like it's not the best time of the year for Indonesia or Philippines, so I might even consider choosing some different random country (Myanmar, Cambodia, Laos?)

Nusa Tenggara was just some random place that seemed off the beaten track, and I usually like such places.

As for the money, $1000 airfare and spending $100 per day is within my budget, especially if this give me a good experience. Philippines being closer is actually an argument against going there, because I can save this destination for the next trip when I have less time.
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#7
I didn't mean to imply that the rain would be a deal breaker. Don't let that stop you from coming, it isn't all that bad. Just wanted to make you aware of the possibility.

In general the best months for Indonesia weather wise are May until September I would say.
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#8
And by no means is Xmas a dealbreaker for the Phils. I have had absolutely incredible times there over the holidays.. like I said, it is just not the usual routine, wihich for someone who used to visit the Phils 10x a year, that was refreshing.. its like all the Pinay goodness and childishness just surges over the holidays.. god i miss that place.. sigh
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