Thanks for all of this Roger! It looks like in the comments you mention Portugal a couple times and I wanted your opinion – we’re looking at the first two weeks and probably focusing on Lisbon to Porto (since we know it will be too cold to do the beaches in the south). While Portugal seems to be highly recommended, I keep seeing conflicting information about November being rainy – we definitely don’t want to spend 2 weeks in the rain but in your experience what are the chances of that? Thank you!!
As for alternatives, you might have a look at my recent article with my recommendations for the best places to go in Asia in December. It’s got many more choices than the article above, with weather information for all of them. Closer to India, I think Sri Lanka is very nice in December, although it’s somewhat similar to India in many ways and you may want something more exotic. In that case I think Thailand and Malaysia are the best choices for family holidays.
If you are going to that region I suggest you visit a site called travelfish.org, which is by far the best website on SE Asia and it’s run by a friend of mine who lives in Bali. They have busy forums where you can ask questions and quickly get them answered by experts on every imaginable topic there. I’m happy to help more as you are planning, so let me know if you have any other questions. -Roger
For anyone considering a multi-destination South American trip in November, Santiago should definitely be looked at. The daytime temperatures should be pleasant and warm, and it's bone-dry all summer, so it's a great combination. Hotels in Santiago don't have their peak price season until New Year's, so in November you'll easily be able to find a very good rate at one of the nicer places.
I’m hearing very mixed things about Cuba visits. The main downside for Americans is that you still have to go as part of a package deal, and those packages are all incredibly expensive for what you get. It sounds like the Cuban government is charging very high taxes and fees on companies selling tours to Americans, so they are really only popular among people who are especially curious about visiting Cuba. In other words, they are poor value unless it’s at the top of your list already. I hope this helps. Let me know if you have any other questions. -Roger
I a from India, Me and and wife plan to go for a quick 4-5 days holiday with an infant who is just 6 mpnths old. so we cannot take long flights, we cannot go to places which are very crowded and hustling and bustling. We want a relaxed holiday where we can take time out and enjoy in true sense. Cannot go to a very cold plave aginst with an infant wont be right. We have been to Thailand( phi phi and kho samui) dubai, bali, singapore, sri lanka already.