I’m currently having morning tea on my patio in sunny Queensland, Australia. As the ad says “Queensland, beautiful one day, perfect the next.” I’m loading up on sunshine before heading to the UK on the weekend 
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We’re in Cuenca, Ecuador in the Andes. Just finished up a cat sit that was a pleasure. A lot of tropical plants to care for though. Temperature today was 75 F, 23 C. Nobody has heat or air conditioning in their home as temperature doesn’t vary much. It’s also on the equator (or near) so length of days is the same. At this time of year it is partly cloudy and a thunderstorm or rain is possible for part of the day. At other times it is clear and the sky at 8,200 feet is a particularly deeper blue.
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We have an upcoming short vacation planned to Spain but mostly northern Spain where we don’t expect it to me much warmer than late November NYC. We are splurging in that it is not a sit! But it’s “off-season” which is a plus for us, and having a THS sitter will help stretch our tourist dollars. Then in January we have a special event and will be going to….. Portland for a sit. Not the sunniest place in January but it’s a city we love, the airfare is cheap, and it will still be warmer than NYC.
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I’m going to New Zealand in February for a 3-week sit.
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I grew up mostly in the tropics, where everyone lived within easy distance to beaches. My childhood home had a 180-degree view of the Pacific and it was warm year round.
By contrast as an adult, I enjoy seasons, including fall and winter. I have zero interest in beach vacations and such, finding them boring. I especially love cities decorated for the holidays. And if it snows, I don’t have to go out, since I work remotely. Then it’s just picturesque.
My husband and I sometimes take winter vacations, but this year we’ll be cozy at home for the holidays.
I’m currently in Italy, staying with a friend for a month, and already have begun missing our lovely central air at home, because it’s cooling off here. All the homes we’ve owned in the U.S. have been toasty warm, and we love decorating for the holidays.
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love Morocco, especially Marrakech. I used to run 5 miles every morning and got lost in the medina in Fes. That was an experience.
I head towards CA and last year, after a trip to Indonesia, I traveled east, TX, Gulport MS, stop in New Orleans, then a few weeks in FL.
This year, just CA, until I start heading back mid Feb as I booked 3 weeks in Scottsdale into early March. Trying to end up in New orleans area for a bit after that before heading north.
Where am I escaping to this season? Bed! So that I can stay warm under the covers until (at least) the middle of January. 
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We’re off on a cruise to Spain, Portugal and Morocco next week. We usually go to Mexico a couple of times a year - one of our favorite warm destinations and not too long a plane flight coming from Canada.
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@Globetrotter, sounds great. Majority of our Canadian winter housesits have been for “snowbirds”. Including three confirmed sits in new year. Often extended duration. Some lovely PP, grand properties and happy pet experiences. Enjoy!
@richten1, winters in Chania, Algarve and Canary Islands - loving your style 
We’ve completed a few housesits in Algarve 
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Suspect that most people would regard low 20s in January as very pleasant indeed!
Re spent several weeks on Madeira in autumn/fall time two years ago. OMG, I did not want to leave the island 
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