Anyone traveling around Christmas/New Years? Where?

[dancingirl21]

My kids are off school from December 23-January 10. DH is a United Platinum member for this year and next year so we are trying to take advantage of flying as much as possible in the next year. After that he will probably lose status since he won't be flying as much for work. We'd like to try and get away for a bit of time during the holiday break. We are open to long weekends or a full week somewhere. We will fly on United or their partners only, and out of Chicago. We don't really care if it's a cold weather or warm weather destination. Trips planned currently (for ideas of where we have been and what we have coming up):

October - Charleston for my sister's wedding
November - Riviera Maya
March '23- skiing in Colorado
July '23 - beach in North Carolina
Fall '23 (still deciding when) - Italy, just DH and I for our 40th birthdays/15 year anniversary

Anyone have recommendations? Is Boston miserable this time of year? I'm assuming yes. We've also thrown around either WDW or Disneyland, but I think it could be a shit show and I'm not sure if I want to deal with all that. What about Canada? The Caribbean is always a maybe but I've looked some and it's soooo expensive during this time, which I would expect. 

[devonpow]

Don’t go to Disney at Christmas - it’s insane!

We are going to Hawaii (the big island), it’s actually our first time ever traveling at Christmas so hopefully it’s ok! Boston isn’t terrible that time of year - it doesn’t get really cold until a touch later usually.

We went to Scottsdale for New Year’s Eve once and it was great.

[dancingirl21]

Sept 16, 2022 18:28:14 GMT -5 devonpow said:

Don’t go to Disney at Christmas - it’s insane!

We are going to Hawaii (the big island), it’s actually our first time ever traveling at Christmas so hopefully it’s ok! Boston isn’t terrible that time of year - it doesn’t get really cold until a touch later usually.

We went to Scottsdale for New Year’s Eve once and it was great.

devonpow DH has shut down Disney. Which I’m more than okay with. We are thinking of going to DC for a few days then flying to Boston for a few, then back to Chicago. Totaling a week or maybe a couple of days more.

[goldengirlz]

We’ve done New Zealand, Hawaii, Puerto Rico and Sonoma over Christmas/NYE and all were awesome in different ways.

This year we really want to go to Japan but flight prices might be cost prohibitive. We’re also looking at Australia, Israel and South America, although same issue with flights. Maybe London. At these prices though, we’ll probably end up in Sonoma again ha. Not that that’s a bad thing!

[erbear]

Both Boston in winter and Disney at Christmas sound like nightmares. I’d go somewhere warm — Costa Rica, the Caribbean.

[mich1]

We went to Paris one Christmas. Another, we cruised around South America. We will be gone on another cruise this coming Christmas.

[Jalapeñomel]

Peru is amazing over Christmas.

[dancingirl21]

Sept 16, 2022 19:16:40 GMT -5 goldengirlz said:

We’ve done New Zealand, Hawaii, Puerto Rico and Sonoma over Christmas/NYE and all were awesome in different ways.

This year we really want to go to Japan but flight prices might be cost prohibitive. We’re also looking at Australia, Israel and South America, although same issue with flights. Maybe London. At these prices though, we’ll probably end up in Sonoma again ha. Not that that’s a bad thing!

I definitely had Europe in mind but $1.5k per person just to get there isn’t happening.

[sdlaura]

Our kids are off 12/23-1/9 so we plan to do big trips in the future once we no longer have a 2-year-old boy. We’re hoping we’ll feel ready to go to New Zealand next winter break. This year we’re just heading to the desert (Palm Springs area) with friends for the New Years weekend to break up the long school break.

[Roc A Bee]

We are going to Mexico for Thanksgiving and Vegas on Christmas Day.

[InBetweenDays]

We're home for Christmas then heading to Schweitzer with another family for a casual ski vacation for NYE.

Other New Years trips we've done are San Jose del Cabo, Mexico; Cabarete DR; Tulum, Mexico; Whistler; and Big Mountain (Whitefish,MT). I think Cabarete was our favorite in terms of activities.

Next year we're hoping to go skiing in Japan. We wanted to do it this year for H's 50th but when we were looking it didn't look like they were allowing tourists

[basilosaurus]

Best time to visit wdw is Mickey's very merry Christmas party. It's in between the peaks of Thanksgiving and Christmas. They shut down the park early afternoon and reopen until 2am. No lines and free hot chocolate and cider (it's potentially colder than you'd expect) with all the Christmas decor.

Obviously it's done when most people can't travel. But if you can swing it, do try. I would not go anywhere near on Christmas.

[basilosaurus]

Sept 17, 2022 1:12:54 GMT -5 InBetweenDays said:

Next year we're hoping to go skiing in Japan. We wanted to do it this year for H's 50th but when we were looking it didn't look like they were allowing tourists

Japanese Alps or Hokkaido? Hokkaido was amazing. I was lucky enough to meet with an instructor on his off day (couch surfing), and we went off piste. Powder up to my waist.

[VillainV]

We’re doing a cruise in the Caribbean. We booked one for March 2020 when our son was 5, and of course had to cancel it. We booked and cancelled two more times after that. The cruise credit never expires, but we really just need to use it, and we REALLY need a vacation.

[sunshineandpinot]

We are skiing Park City over NY.

Have you done NYC? Could easily combine with DC and it's just magical over the holidays.

We had a great time in Boston last fall, loved it. I just can't speak for the weather.

It would be a great time of year to visit New Orleans though you really just need a long weekend.

Panama? Cabo? Costa Rica? I'm trying to think of where my H frequently goes. (United pilot- Thanks for supporting united!
San Fran and or San Diego? I love CA and you could do a lot in a week, 10 days.

[mambo123]

We are flying into St Maarten and island hopping from there.

We just came back from Panama, and loved it. Very economical once you are on the ground. Also check Belize. Costa Rica will probably be $$. Keep poking around in Europe from DC flights are under $500 for that time for some cities. Driving the Pacific Coast Highway or something like that could be nice too!

[freshsqueezed]

We’ve been thinking about Montréal/Quebec City.

[sunshineandpinot]

Sept 17, 2022 7:27:34 GMT -5 freshsqueezed said:

We’ve been thinking about Montréal/Quebec City.

This is a great idea if you're not opposed to potentially really cold weather. I've heard great things and I think it's supposed to be awesome around the holidays. 

[karinothing]

I really wanted to travel this yr (we never do) but there break is from thr 19th to the 2nd. We would travel b4 Christmas because the Christmas to NYE week is always $$ BUT I am too nervous to get covid before Xmas.

[karinothing]

Sept 17, 2022 7:27:34 GMT -5 freshsqueezed said:

We’ve been thinking about Montréal/Quebec City.

Oh I thought about this but it seemed very cold lol. I chickened out ha

[freshsqueezed]

Sept 17, 2022 8:09:53 GMT -5 sunshineandpinot said:

Sept 17, 2022 7:27:34 GMT -5 freshsqueezed said:

We’ve been thinking about Montréal/Quebec City.

This is a great idea if you're not opposed to potentially really cold weather. I've heard great things and I think it's supposed to be awesome around the holidays. 

Yes. I have only been to Montréal in summer but I hear QC is similar to Europe at Christmas. I love Europe at Christmas but not looking to go that far so I’d like to check this out. I’m also far more afraid of hot weather than I am cold so that helps LOL

[runblondie26]

We’re going to the Florida Keys for the week. DH wants to do some fishing charters, and I just want to go somewhere warm and laid back (we live about an hour north of Boston). I’m looking forward to a break from the traditional Christmas stuff this year.

[letsgetweird]

I'm going to Costa Rica

[InBetweenDays]

Sept 17, 2022 4:26:36 GMT -5 basilosaurus said:

Sept 17, 2022 1:12:54 GMT -5 InBetweenDays said:

Next year we're hoping to go skiing in Japan. We wanted to do it this year for H's 50th but when we were looking it didn't look like they were allowing tourists

Japanese Alps or Hokkaido? Hokkaido was amazing. I was lucky enough to meet with an instructor on his off day (couch surfing), and we went off piste. Powder up to my waist.

I don't know, this is all H planning so I'm not sure what specific area he is thinking. But that is good information!!!