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DBoy: How possible is a day trip to Melaka from SIN? How about a day in Melaka and one in KL, getting back to SIN late at night to fly out the next morning, is that doable?
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A day trip to Melaka by bus is too much.
Melaka is an interesting city, full of history and probably the closest city worth spending time in as a tourist, in Malaysia. It's a nice 5 hour trip by bus, which includes time for the border crossing.
I don't know about flights.

Melaka to Kuala Lumpur is another 6 hours by bus. I think there are shuttle flights on Singapore and Malaysian airlines from SIN to KL, maybe $60 each way?? That could pay for itself in shopping savings if you like fake Rolex's, knock off designer clothes, CD's and bootleg software ($3 per software CD).

I'm loving Malaysia, but if I only had 2 days, I'd spend it in SIN.