For those of you who have gone on a vacation to a nice warm place in the middle of a cold winter: is it worse when you get back then if you had never gone?
We went to Cuba a couple of years ago for Christmas. Came back to -30 C and a snowstorm. (It was so cold the luggage door on the plane froze shut and we had to wait an extra hour to get our luggage.)
It was well worth it. 
We spent last week in Puerto Rico, and got home last night. It snowed here today.
It’s nice to be cool and not-sweaty. I don’t think it feels colder than it would have if we hadn’t gone. There’s definitely a contrast, but we like it up here. (And we totally dug PR, too.)
It’s worth it to get some sun and heat. Yeah, re-entry is a bitch. It’s still worth it.
I’ll let you know - right now I’m in Australia and will return to the northeast U.S. in about 10 days.
I live in the Boston area where people, especially me, take vacations to the warmer climes during the winter months. Many of them, including me again, develop some serious relocation plans during those trips. Yes it is worth it. Seasonal affective disorder is a real thing and spending a week in the Caribbean, Central America or Mexico can work wonders to break up the seemingly endless New England winter.
It is still going to suck when you get back but that is much less worse than not going at all and you will have full stores of vitamin D to combat the suckitude until it gets better at home.
Well, if you’re feeling suicidal over lack of sun and vitamin D, getting a week of sun is awesome. The return sucks, but doesn’t suck as bad as if you had continuous clouds for months on end
Each January we spend a week or two in St Martin.
Returning home, average temps drop from 80 to 10. It sucks. The cold feels colder for about a week and I whine about it.
C’est la vie.
I live in Canada and travel south regularly.
I have spent ~2 weeks in Florida every winter for the last 5 years.
Back in my 20s, I went to Florida or Mexico almost every year.
I’d say it’s much better going than not going at all. The break from the cold, miserable and dreary weather really helps to keep your mental health. I usually feel great for a week or two before the doldrums set in. 
Of course, if you go later in the season, it’s possible that when you come back spring has begun.
This year I’m in Florida for two weeks over Christmas and then 10 days in Costa Rica in March!
With one exception, I have spent 2 or 3 weeks in Barbados every year since 2001. Since I keep going back, you have to believe that I think it worth it. You might as well ask if I regret summer because it interrupts winter. I figure that the less winter I get the better. Of course YMMV.
Hm…
Were this last year, or the year before last, it wouldn’t have been so bad. We missed out on Winter the last two years. This year, it looks like we’re having a ‘normal’ Winter. So when I started work this morning, it was 24ºF. Kind of missing being hot and sweaty right now…
In Hawai’i right now. I understand it snowed right after we left. I’m assuming it will again after we get back.
I haven’t ever noticed a re-entry pain, although my husband is busily making plans for acquiring a second house over here. 
In general, we tend to like the climate where live, so it’s nice to here, and nice to get home. I’ll confirm again in a few days. 
I vote, totally worth it.
do you have an opening in your family unit?
Back when I lived in gray+snow country that was my attitude.
You would *return *to the cold weather after a few weeks in the Caribbean in winter?
Cold is when I need to close the windows at night.
I had Christmas off last year and I traveled even closer to the equator!
Iggy - 14 years in Cayman
When we lived in Kashmir, we used to run to the Maldives in December for a week. They had to drag us kicking and screaming to the plane for the flight back.
It’s all in the definition of “warm weather”. Clan Piper is currently on a warm weather vacation in London and Paris. For us, temps of 5 to 15 degrees in December is warm weather! Facebook posts from friends back home indicate they’re dealing with temps of -30 C, -40 C with windchill. Curiously, they’re no longer responding to our posts about the lovely weather we’re having…
ETA: to reply to the OP, we’re hoping we won’t be having a rough re-entry on return, but are willing to take the chance!
ETA 2: Mrs Piper just advised that Enviro Canada has issued an extreme cold weather warning for all of southern Sask: now predicting -43C.
We’ve done this several times and wish we could do so again. We have usually gone in late January or early February. Through the bitter nastiness of January we tell ourselves, “Yes, but in a few weeks we’ll be warm!” When we get back, we tell ourselves, “It’s only a few weeks until spring!”
Whether I’m living in the cold or the warm part of the country that pesky job thing still involves visiting the cold part pretty often. Or at least it did.
I usually asked for annual vacation in February. Other guys would look at me like I was nuts; they wanted summer off to travel with kids. Or they wanted Thanksgiving through Christmas off to be with the kids. Or something. Vacation in February was heresy; nobody in their right mind would want that!
Not having kids, my only goal was to avoid spending all of February slogging around in the snow and ice and delays and cancellations and diverts. Wife and I would go to the Bahamas or Mexico or … for most of the month.
I’d get back with a tan and work would be full of war stories like: “I got stuck in that big ice storm in Dayton last week. Took 2 extra days to get home. How about you?” “Me? I missed that. I was too busy drinking Pusser’s Rum on a catamaran sunset booze cruise.”
By far the best part about winter is being elsewhere while it happens. If you can avoid all 3-5 months of it, great. If not, avoid as much as you can even if it’s only 3 days.
My bottom line: It’s definitely better to return to winter than to have never left it at all.
I am with you on that. I live in New England. Summer is fine and I have a pool. Every day can be a vacation after work if I want and all day on the weekends. Other people pay stupid amounts of money to be here during that time after all. The month of Fall is really fun (I say that because it is still technically Fall right now even though I am almost snowed in). The holiday season works out pretty well too because I work in a seasonal line of work and I am happy to be there when you don’t have to do much of anything and can leave early without taking any vacation days.
OTOH, January and February suck. There are no good holidays and the weather ranges from terrible to horrific. That is when I hit the road. Whether it is Costa Rica, Florida, New Orleans or the Virgin Islands, it is all good and very necessary for a white boy like me to recharge with some sunshine.
The additional bonus is that few people travel during that time of the year so you can get some really good deals and avoid beginning of year meetings.