Don’t be too shy to ask the wait staff how the food is prepared. If you suspect something might be breaded ask. Ask if any of the dressings have sugar in them. In Italy it’s not common at all for savoury food to contain any sugar, even the sauces. Most are based on olive oil or cream. If you order a steak without any sauce don’t be afraid to ask for olive oil to use on it. You might get some strange looks if you ask for butter and they might not have any available. Try to go for roasted or grilled food rather than fried as even in Italy, the spiritual home of olive oil, the food is usually fried in vegetable oils. Also don’t be afraid to ask for substitutions. I don’t like bell peppers and they always come as part of grilled vegetable sides. I simply ask them to leave them out and I’ll get more of another type of vegetable instead.
Thailand is far more different and it’s easier to get around. The tourist areas are quite modern and well organized, and enough people speak English that it’s easy to do whatever you like. Again there you have choices of cooler areas in the north such as Chiang Mai, and of course Bangkok, as well as all of the islands. Let me know if you have any questions. -Roger
My top recommendation would be San Juan, Puerto Rico. It offers a wonderful mix of history and culture and nightlife and great food, alongside excellent beaches and abundant activities. Hotels and rental apartments are mostly in the mid-range for the Caribbean, but food and drinks and most other things are great value. You could get a place in the Condado area, which is close to the lovely Old San Juan neighborhood and plenty of nightlife all around. And then perhaps you could rent a car and stay for a few days at one of the smaller beach towns elsewhere on the island. You wouldn’t even need a passport, although it does feel fairly exotic while you are there. But because it’s part of the US, it’s also well organized and safe. Most people you’ll meet will speak at least some English, and many are fluent, so it’s easy even if you don’t speak Spanish.
I’d recommend 1 night in Auckland, then 3 nights on the North Island, and then a ferry to the South Island. If you can spend a week there, and return the camper van or car to Christchurch for a flight to Auckland and home, it would be perfect. As long as you can spend at least 4 nights on the South Island, it will be worth it. But if your schedule or budget don’t allow that much, you might just stay on the North Island. The most interesting place on the South Island is Queenstown, but there is plenty to see all over.
Needless to say, Australia is a huge country so you could spend 6 months there and not get bored, or you could spend one week there and barely see any of it. The obvious destinations are Sydney and Melbourne, both with plenty to do for non-beach people. Melbourne is known a bit more for culture and food, while Sydney is more pleasant and still very interesting. There is also the Great Ocean Road, which is a very scenic drive just a bit south of Melbourne.
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.
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
However, I would probably recommend staying closer to the US, unless you are really interested in the Asian cultures or that kind of experience. If you are mainly just interested in family time and a fairly easy holiday for all, and you aren’t specifically interested in getting to know an Asian culture and its food, I think I’d stay in the Americas.
From November through February there are literally no European cities that could qualify as having “great weather.” We list Tenerife below because it's technically in Europe, although not really much of a cultural destination. Antalya, Turkey (which technically isn't even in Europe), has the closest thing to a sunny climate with acceptable temperatures. So during the winter Europe is all about cultural tourism, and lower hotel prices make it especially appealing for those who like to stretch their travel budgets and avoid crowds at the same time.
You still get warm ocean breezes and 70-degree temperatures, plus the Hawaiian islands go all out for the holidays. Locals host potlatch-style parties where the Christmas goose is replaced by a luau pig, and the resorts deck themselves out like tropical North Poles, including a massive tree-lighting ceremony at the Outrigger on Oahu and tree-decorating contests at Mauna Kea on the Big Island. Residents there climb to the top of the 13,000-foot-tall volcano, shovel snow into their trucks and speed back down to build snowmen in their yards before it melts.
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.
Blisteringly hot in summer, Tokyo is a breeze in the cooler months. Fight the dizzying jet lag and head out for the world's best sushi or ramen, shop in the city's amazing department stores, and visit the parks surrounding the Imperial Palace in the center of the city. Escape the crowds somewhat by heading to Yanaka Ginza, which retains a bit of old Tokyo and has plenty of places to eat and shop. Do make time for a side trip to Hakone, where you can visit a Shinto shrine and see magnificent Mount Fuji on a clear day.