From the Art Deco architecture to fabulous restaurants and nightlife, Miami is truly a city that appeals to every type of traveler. Art and culture lovers should plan a trip during Art Basel, which officially kicks off on December 6. The weeklong affair attracts celebrities, tastemakers, and bold-faced names, who come for the world-renowned art exhibitions, but stay for the swanky parties and events. Be sure to book a hotel well in advance, as prices skyrocket and availability becomes increasingly limited.
I’m happy to hear that this information is helpful. My first thought is to wonder if you’ve been to Goa yet? I’ve spent 4 total months in India to about 15 different places, and I know all about the insane crowds and whatnot that you would prefer to avoid. In my experience, Goa is totally different, and that’s where I’ve spent by far the most time. I remember spending time on Calungute Beach and I was surrounded by mostly domestic Indian visitors including many families. There are other beach towns and areas that are even more mellow in the south. The beaches there are quite nice as well, which is something I didn’t find as much of in Kerala, Putacherry, or even Puri. At least it would be the fastest and most affordable destination, and it should be very nice in December.
I too am a planner, which is how I got involved in this, and so I totally understand your motivation. I think your plan sounds quite good. The weather in the places you are planning is actually fairly mild, and none of them are too far north. For some of us it’s easy to forget how far north parts of Europe are, and in those areas it’s not so much the cold but the fact that the sun rises at 10am and sets at 3pm that time of the year.
Heading east, India could be a possibility, although it’s not for the faint of heart. As a resident of Singapore, I assume you know a fair bit about India. Outside of Mumbai, it’s all quite cheap and the weather will at least be good. Personally, I love the southern state of Goa, and it has everything you are looking for, without the insanely crowded conditions of India’s big cities.
While the Caribbean destination tends to overflow with families during the holidays in December, go a month earlier and you’ll be treated to sunny days sans screaming kids, plus less expensive airfare. “November is my one my favorite months. The hustle and bustle of high season hasn't kicked in, average temperatures are in the 80’s, and the water temperature is lovely,” says Michael King-Hew, the proprietor of Kamalame Cay, a private island resort in the Bahamas. King-Hew specifically suggests for the resort's annual wellness retreat. “It’s the perfect way to get rested and in shape before the start of the hectic holiday season.”
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.

To the life aquatic now and Micronesia’s little-known islands scattered in the Pacific Ocean, which serve as the mating grounds for giant manta rays. With wingspans that can reach up to 5m, the chance to dive alongside these dancing behemoths shouldn’t be missed. From colossal to downright cute, rare (and ridiculously adorable) pygmy hippos can be found in Sierra Leone, once you've had your fill of lounging on palm-fringed beaches.
Another reason to consider Dubai is that the busy airport has cheap non-stop flights coming in from almost every major airport in Europe and Asia. As a result it's popular to book long weekend trips of 3 or 4 days to Dubai, where you can enjoy some sunshine and shopping before flying back home where it gets colder by the day. You might also consider stopping for a few days in Dubai and then moving onto somewhere else with cheap direct flights such as the Maldives.

I have been reading the thread with great interest. I took my 2 daughters aged 11 and 18 to SE Asia in December and they loved it. Siem Reap – lovely vibe over new year and not too busy. Would stay longer than 3 days because the heat and humidity slows you down and you would rather want to cool down in the hotel pool in afternoons and try and squeeze in more than 1 wat in a day. Easy to get around and good food and vibe in Pub Street.
“Winter in Eastern Canada” might sound more like a 19th-century prison sentence than it does a pleasant vacation, but Quebec City does the cold better than anywhere in North America. Blanketed in snow, QC looks like the world’s most elaborately constructed Christmas village. The cobblestone streets in Old Quebec densely packed with storefronts beckoning you to come in for hot food and baked goods, and boisterous bars overflow with a cacophony of Quebecoise. In December the streets are draped with Christmas wreaths and populated with carolers, plus there’s an authentic German Christmas market -- a true novelty in a city so overwhelmingly French.

Traveling during the last ten days of December means crowds and exorbitant prices throughout much of the world, but the first two-thirds of the month—before holiday airfares and hotel rates go into effect—can be a serene, value-laden, and just plain lovely time to vacation. Europe is all decked out for the holidays—with locals generally friendly and in high spirits; in the Southern Hemisphere, spring is in bloom; and in the Caribbean, Hawaii, and Mexico, hurricane season is over, the weather is gorgeous, and there are free upgrades galore.
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