This is a tricky one. Pretty much every destination in the Tropics has its peak rates of the year during the weeks you have in mind. That said, there are still some fairly cheap destinations in the Caribbean, even at peak rates. However, since you live in South Florida and understandably don’t want to go someplace even hotter during the only semi cool time of the year, it sounds like you are ruling out most of the Tropics.
You mention New Zealand and of course it’s summer there then, so it would be a good choice. However, all of these places will be crowded and near peak hotel rates if they are warm. So I’ll be happy to give you advice if you tell me if you’d rather visit one or more European cities in the cold season, or if you are looking for a warm place like New Zealand where it will be fairly crowded. By the way, the southern European cities such as Rome and Barcelona are lively and enjoyable that time of year, as the Christmas season goes on, and there aren’t too many tourists except for a few that travel to see their families around the holidays. So it can be a good time for southern Europe, as long as you don’t mind wearing a jacket or jumper during the day, and maybe a bit more in the evening. Give me a bit more guidance and I’ll be happy to try to help. -Roger
Thank you. I think Kauai, Cancun, and Costa Rica could all be good choices for you. You’ll be looking at the last month (more or less) of the rainy season in each of them, but in the Tropics that usually means at most a few quick thunderstorms per week that typically last only 30 minutes or so. Kauai would be the most expensive of the three, although the most beautiful as well, and the easiest to visit since Spanish isn’t necessary at all.
And as far as I can see, Bali is totally up and running as of now. A friend of mine is a driver there and he has a steady stream of foreign guests who are going all over the island with no difficulties. November is a pretty good month in that it’s not too busy, so that’s another reason it might be a good choice. Let me know if you have any other questions. -Roger
When you mention, “not too touristy”, the first thing that comes to mind is San Juan, Puerto Rico. I’m not sure if you’ve been there already or not, but one great thing about it is that the “tourist” areas close to Old San Juan are filled more with apartments than with hotels, unlike Cancun, where it’s nothing but hotels and timeshares. I can highly recommend the Condado neighborhood, which does have some large hotels but is mostly apartments for expats and seasonal visitors. There is even a free bus that goes from there to the heart of Old San Juan, which is a gorgeous colonial town filled with great restaurants, bars, and interesting attractions.
One thing I can assure you of is that those countries are very modern and well organized, and they know how to deal with winters well. So you really don’t have to worry about getting stuck or things being cancelled. As for getting around, the trains are modern, and they can be reasonably priced if you buy a couple months in advance. Otherwise, flying is probably your best bet because it’s a large area and you’ll probably want to go well to the north, and the trains might take many hours. You could even rent a car, which could be good if there is more than one or two of you. Have a great trip. -Roger
Bali has nice weather in the first half of November and it’s very family friendly as long as you don’t stay on the nightlife streets of Kuta Beach. That is possibly your best choice. Dubai has great weather in November as well, and it’s very kid-friendly. There are shopping malls there that also have huge and modern play centers that are sort of like amusement parks there. And there are nice beaches as well. It’s unfortunate that the weather close to India limits your choices that time of year, but either of those could be great and they are both fairly affordable with frequent flights. Let me know if you have any other questions. -Roger
If you are referring to days trips and that sort of thing, it will be much cheaper if you book once you get there. In Vietnam in particular it’s amazing how cheap tours can be if you book them through your hotel. I once did a 6-hour bus tour to Mỹ Sơn, which is near Hoi An, and I think I paid about US$6. It even included a boat ride and a basic lunch. That same day tour online would probably cost US$30 because the booking company takes a share and there is very little competition. 

My family and I are planning our first trip to Europe for the last week of December (2018) and the first week of January (2019), I know this is a long way off but I am a planner and to me that is half the fun! I know to most people that time of year in Europe is not ideal, but we LOVE cold weather, snow, rain, etc. and I am drawn to the lower prices and smaller crowds. So far I am considering Rome for 6 nights, Venice for 2 and Munich for 6 nights. I want to take day trips from Rome to see Pompeii & the Amalfi Coast and from Munich to see Rothenburg and Nuremburg. Does this seem like a good itinerary? Since I love the cold weather are there any other itineraries you think would be ideal for that time of year? Any advice you have would be very much appreciated.


The park we visited has an app you can download on your phone that allows you to reserve a table at any table service restaurant on their property ahead of time. The app also lists the daily breakfast, lunch, and dinner offerings at every single food establishment on site. There really is no excuse for settling for the popcorn or french fries when you can easily find a place with compliant options if you’re willing to look and tweak a bit. A lot of other theme parks are either offering similar apps or putting their information online for those who need to research their options ahead of time. If your destination is the beach or a famous city, check out what’s in the area online, or call your hotel to get an idea.
When you mention, “not too touristy”, the first thing that comes to mind is San Juan, Puerto Rico. I’m not sure if you’ve been there already or not, but one great thing about it is that the “tourist” areas close to Old San Juan are filled more with apartments than with hotels, unlike Cancun, where it’s nothing but hotels and timeshares. I can highly recommend the Condado neighborhood, which does have some large hotels but is mostly apartments for expats and seasonal visitors. There is even a free bus that goes from there to the heart of Old San Juan, which is a gorgeous colonial town filled with great restaurants, bars, and interesting attractions.
Brazil, on the other hand, has a famous problem with petty crime in tourist areas so I wouldn’t recommend it for a woman and young child. Another to consider is Puerto Rico, which has a lot to offer including great weather, and it’s also more or less part of the US, so it’s fairly safe and well organized. Hotels in Puerto Rico are a bit expensive, but you should be able to get an apartment rental in the San Juan area (gorgeous, by the way) for a modest price if you are staying for more than a few days. Let me know if you have any other questions. -Roger
As for my own Top 10 destinations in general, that’s a tough one for someone like me because I can’t help but factor costs into the equation. For example, I really love Amsterdam and I even lived there for awhile, but it’s also very expensive and maybe not a great choice for everyone. And it’s also hard to avoid cliches for a list like this, because I honestly feel that most of the places on these sorts of lists are great.
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.

If those flights are too expensive you might think about going somewhere else in Mexico or to Costa Rica. The area around Cancun including Playa del Carmen and Tulum and Cozumel has a LOT going on. And if you’ve been there you could instead go to the Puerto Vallarta area, which is very different and also great. For activities though it’s hard to beat Costa Rica. I think they invented zip-lining and the country is about one-third national parks with all kinds of fun activities. Let me know if you have any other questions. -Roger

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