You’ve got a pretty good budget so you can afford to go almost anywhere, assuming you are okay with renting one or two houses or villas instead of 4 hotel rooms. If you are willing to fly all the way to Asia, your best bets would be Bali or one of the Thai islands, probably Ko Samui or Phuket. In all of those places you should be able to rent a house or villa near the beach and then do activities and day trips very easily.
We spent a month in Costa Rica last year and although we thoroughly enjoyed the trip, we don’t tend to be “repeat customers”, so we’d like to venture somewhere new (we saw that you had mentioned this as kid-friendly a few times, so just wanted to let you know that we’ve already been there). Some available attractions and activities would be ideal, but, we’d also quite enjoy the beach towns of some sort. We love hostel type of accommodations, aren’t overly-indulgent and can get by on a fairly modest budget. We are of the mind-set that spending more time, is more valuable than spending more money.
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.
Fortunately, Bangkok remains very cheap by almost anyone's standards. If you want to splash down for a nice 3-star room then it'll be half the price of a similar room in Europe or the US, and if you are fine with something more basic then you can find a room for next to nothing, even in the fun Khaosan Road backpacker district. Street meals for around a dollar are always there too, so you'll be able to afford a bit more for a room anyway.
The Norwegian coastal city of Tromso, located more than 200 miles north of the Arctic Circle, is an enchanting winter wonderland in December. During the Polar Nights — when there is no sun at all — the opportunity to witness the Northern Lights is greatly increased. For another awesome view, take a cable car or an adventurous hike up to Floya, overlooking the city of Tromso and the surrounding mountains and fjords. The Polaria Arctic Experience Center and Aquarium is a family-friendly destination, both educational and fun. The 360-degree Planetarium at the Science Center in Tromso is another family option with breathtaking photos and a lifelike video of the Northern Lights. Stroll along Storage Street to be amazed at the number of cafes, restaurants, pubs, and shops featuring artwork, clothing, and crafts by local artisans. Mack’s famous Olhallen beer hall, established in 1928, is Tromso’s oldest pub, boasting Europe’s longest tap beer tower and a micro brewery. Their acclaimed Christmas Beer is released every December. Experience the Tromso wilderness on a dog sled or chase the glowing night sky on a reindeer sled with a native Sami guide. Tours range from four hours to five days. Whale watching is also ideal in December when humpbacks, killer whales, and several other species thrive on the plentiful herring fish in the fjords. Downhill and cross-country skiing opportunities abound for all skill levels.
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Montreal’s oldest Catholic Church, dating to 1656, includes stained glass that chronicles the history of the city. The city’s Parisian-style historic district, with cultural landmarks, boutiques, cafes, and restaurants, can be toured in a horse-drawn carriage for the full vintage effect. La Grande Degustation de Montreal (Nov. 2-3) attracts wine producers, distillers, and brewers from around the world. Montreal also hosts the 24th-annual French Language Film Festival (Nov. 1-11) featuring contemporary films from around the world subtitled in English. When it’s cold, visitors can head to the underground city, a network of tunnels, corridors, and plazas with more than 1,000 retailers and restaurants. The Montreal Tower Observatory, the world’s tallest inclined tower, provides breathtaking views of the city, the Laurentian Mountains, and St. Lawrence River Valley.
Most hotels these days include at least a small refrigerator, and some even include a full kitchen and stove. This is great because it allows you to shop locally for some fresh food options. Search online for nearby farmer’s markets or grocery stores and see if you can pick up some local meats or fresh veggies to have in your room. This is more likely to be an option in the warmer months.
This is a difficult question to answer without quite a bit more information. First off, it’s obviously going to be pretty cold in most of Europe that time of year, although most of the major cities aren’t known for accumulations of snow. As long as you are okay with cold weather then it’s mostly down to budget and your main interests. I’m guessing that you haven’t been to Europe yet since you didn’t mention any places that you’d prefer to skip this time.
Mid- to late-November welcomes warm, dry sunshine with temperatures of about 80 degrees in this subtropical Central American nation located south of Mexico. You’ll slip in before the holiday crowds and enjoy exceptional weather and affordable prices for tours and fine lodging. White sandy beaches, friendly native people, jungle adventures, and tours of ancient Mayan ruins await visitors on this small and easy to navigate paradise. Nov. 19 is Garifuna Settlement Day, a celebration of the Garifuna people, descendants of African slaves and native Carib islanders. All are welcome to participate in dancing, parades and tasting traditional foods.
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Vietnam might fit the bill for what you are looking for. The most popular itineraries are to start in Hanoi and end up in Ho Chi Minh City, or the other way around. There is a nice train connecting them that is scenic in many places, and the best must-stop place in between them is Hoi An. You also don’t want to miss Halong Bay, which is just outside Hanoi. Vietnam mostly attracts cultural travelers rather than party people. The food is excellent (France used to run the place) and there is plenty of culture all around, in addition to some nice beaches in Nha Trang and Da Nang (next to Hoi An).
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.

We were able to sit down in the store, relax, and eat our salmon and cheese  (pictured above) – separately of course! As you eat, you can watch them hand make their cheese through a glass window, showing exactly what they do in their process to get the food you’re eating in front of you. An experience in itself that I definitely would recommend to anyone visiting this city!

Aside from that, this is a bit tricky because you obviously want to avoid longer flights for a short trip and especially with an infant. And some of the closer options are not close to a major airport, so they are still hard to reach in half a day or so. I think if you want to go farther than Goa, it’s probably best to look for other options in Thailand. As you know from previous visits, Thailand really has tourism figured out and it feels safe and well organized there. Cambodia and Vietnam also have beaches, but none that I’d recommend for a short trip. It’s the same with the Philippines, and the flights start getting longer. Phuket is the largest Thai island by far and it’s got over a dozen different beach areas and towns to choose from. Patong Beach is the main beach town and I wouldn’t recommend it for a family, but Kata and Karon beaches are just south of that, and they are nicely family oriented. Phuket also has a large airport, so getting there quickly is pretty easy compared to other beaches and islands in the area. Phuket’s beaches are also very nice. I wish I had more suggestions for you. Let me know if you have any other questions. -Roger
Looking to shake up the traditional holiday season table? We’ve got just the foodie forays for you this festive month. Tuck into a spicy blend of fabulous flavours at Malaysia’s hawker food stalls, where bright bowls of creamy laksa (noodle soup) and deliciously deep-fried lor bak (pork or prawn wrapped in tofu skin, deep fried and served with dips) will soon do away with any cravings for Christmas pudding. With tourist numbers low, now is the ideal time to visit Spain’s Basque Country, seeing out the year with a plate piled high with pintxos (tapas); or check out Cuba’s capital, exploring the crumbling, colonial architecture with a rum-based cocktail in hand.
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