December is the end of the rainy season in Boracay, but by the middle of December you would probably only get a few quick tropical showers a week. Room rates are a bit lower at that time as well, so it can be a great time to visit. If you were looking for a place to go for 2 or 3 days, I wouldn’t recommend it because it does take some time to get there and you could be a bit unlucky with the rain. But if you are going for longer than that I’d highly recommend it. It’s a wonderful little island that feels like you’ve gone back in time to before mass-market tourism in places like Phuket.
Aside from Indonesia you might also consider Thailand, which has great infrastructure so it’s much easier to travel with young children. Phuket has by far the most options, and its rainy season usually ends in early November. For families I recommend Kata Beach and Karon Beach, which are both just south of the main shopping and nightlife town of Patong Beach.
Still, this is a perfect time of year to find bargains, as the full-on busy season doesn't begin until mid December. You might have to stay a few blocks off the main tourist strip if you are looking for something in a backpacker price range, but fortunately there are still plenty of very cheap restaurants and bars all over the city if you scan the menus carefully.

Unfortunately, it can be a bit complicated and time consuming to reach any of these Philippines resort areas. I don’t think I’d recommend doing more than 2 of them in a 8 to 10 day trip. The nice thing is that they are very secluded-feeling once you get there because they are so out of the way. Partly for that reason, I think staying for 4 or 5 days each is very nice.
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Australia’s capital has been voted the world’s most livable city—for the seven years in a row. If that isn’t reason enough to go, what is? Here's another: the artsy cosmopolitan city promises pleasant temperatures in the high 60s throughout November. Book a room at one of the area's buzziest spots, QT Melbourne, a design-centric boutique in the city’s fashion district.
My fiance and I plan to travel for a month starting Oct. 20. We’re thinking about selecting a region that would allow 4 destinations with great food, outdoor activities (hiking, swimming, horses, yoga, etc), nice accommodations that don’t break the bank, and some sight-seeing. We’re planning to get married on the trip, too. Any suggestions? Super appreciate your insight!

And as you mention, Bali could actually work for you. I’ve spent two Decembers in Bali, and December is quite a bit rainier on average. Still I had a great time and it was sunny most of the days. The rain in the tropics (and Bali is almost ON the equator) tends to come down in 30-minute bursts rather than drizzling all day, so it’s usually pretty easy to avoid. The best part of Bali is there are loads of things to see and do, and the nightlife is excellent. The Kuta Beach area is fun for at least a few days, but I wouldn’t spend too much time there. You should also spend a few days in Ubud, which is very touristy but also interesting. And you could spend some time in Lovina, which is along the northern coast and it has all of the charm of Bali from 20 years ago before most of it got overbuilt. With all the temples and other local attractions, there is always something interesting to do, which is not true of many other places with great beaches and nightlife. Let me know if you have any other questions. -Roger

Southeast Asia is easier to deal with, and there are cheap flights connecting in the Middle East and landing in Bangkok, Kuala Lumpur, and Singapore. Each of those is a very interesting city, and there are many smaller places to go in the same region. In Malaysia there is Penang and Melaka. In Thailand there is Chiang Mai and quite a few others in that area. In Laos you can visit Luang Prabang, which sounds like it could be a winner for you. And there is also Siem Reap, which is home to the amazing Angkor Wat temple complex.
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