Winter vacation destination recos for large multigenerational family?
July 23, 2023 7:34 AM   Subscribe

My family flies to get together every Christmas season (none of us live near each other). We now consist of three generations of several adults and several kids. Where can we go that will fit all of us and have things to do for ages 2 through 80? Details inside.

We are looking for a destination/resort/ranch/hotel/glamp/anything that fulfills the following:

1) Warm weather (not interested in skiing or winter sports)
2) *Ideally* provides one building that can house us all (it's grandma's dream to have everyone be in one space to sit and talk together, eat together, play together, etc). But open to other options.
3) Convenient for a large group that includes young children all the way to senior citizens. "Getting around" is hard -- want to avoid having to pile in to multiple cars with multiple car seats just to get a meal, for example.
4) US location preference, but open to other countries.
5) Bonus if there are family-friendly things to do

We've never done an all inclusive resort but I am wondering if that could be an option.

Can pretend budget is not a concern for this question.

We've been struggling with this for years and I can't believe it took me this long to turn to this community! Really looking forward to your ideas--thank you!
posted by dede to Travel & Transportation (17 answers total) 5 users marked this as a favorite
 
If money is no object, this is pretty much why prices in Hawaii are so high at Christmastime. I know a lot of people on the West Coast who book the same enormous vacation rental or block of rooms in the same resort in January every year.
posted by potrzebie at 8:14 AM on July 23, 2023


That said, it might be helpful to specify the scale of this gathering. 15 people is much easier to accommodate in a single capacious vacation rental than 50.
posted by potrzebie at 8:29 AM on July 23, 2023 [1 favorite]


Having planned something like this myself, cooking/cleaning for a dozen+ people 3x every day is a huge lift and can quickly become a source of tension. An all-inclusive makes a ton of sense for that reason. Cancun/Mexican Riviera is easy for midwest and east coast people, a little less so for west coast - there are dozens of all inclusives at different price points there. I'm not familiar with US destinations with lots of all-inclusive choices, but I suppose Florida would be the place to look for warm weather at Christmas.

A big airbnb in FL or CA is another option, but friends who have done this successfully have had to create a schedule of meal prep and assign meals to specific families/couples. If money is truly no object you could look at a private chef and a big airbnb. Palm springs is a great destination for "rent a giant house and get a chef," as one possibility.
posted by Mid at 9:06 AM on July 23, 2023 [1 favorite]


I think the west coast of Oaxaca, like Puerto Escondido or a resort nearby would be ideal for this. The temperature is pleasant, and there is a huge variety of accommodations. I feel it is more family friendly than Cancun, but suddenly realized while writing that it is 20 years since I've been in Mexico. On the other hand, this is what my Mexican family thinks, too.
posted by mumimor at 9:13 AM on July 23, 2023


Knowing how many people would be good. First thoughts are Arizona or Puerto Rico for the weather and no passports required but I can't recommend specific places.
posted by fiercekitten at 9:20 AM on July 23, 2023


I'll add to the mention of Palm Springs, the whole area of Yucca Valley/Joshua Tree/29 Palms. You could find rentals (and ones for big groups exist) close enough to be able to walk to restaurants. You would need to drive to get into Joshua Tree NP, but it is one of the more family-friendly parks I've been to (at least in the winter). A lot of the most popular hikes are short and flat, and kids like clambering up the big rocks. Plus it's relatively close to the Vegas airport, a major hub with cheap flights.
posted by coffeecat at 9:57 AM on July 23, 2023


Last Christmas my family organized a Caribbean cruise for 36 people aged 1-75. Great setup, if you can look the other way on the ethics of cruising. We had 4 large tables for dinner every night. A Christmas miracle that everyone got there given the weather and flight disruptions.
posted by shock muppet at 11:13 AM on July 23, 2023


It's been my observation that renting an entire house for a large group can cause friction in a way that renting individual sleeping quarters does not.

I think it might be worth working with a good travel agent on this.

While cruising isn't without its own set of issues, it can be a good fit for multi generational families. Especially if individual family units are are paying their own way, each family can decide which cabin type fits their needs and budget (although "someone probably grandma" may want to get a suite to have a private space to 'host' family. Food is included and can accommodate different dietary needs and preferences.
posted by oceano at 11:21 AM on July 23, 2023 [1 favorite]


I would also recommend talking to a travel agent, because they will know how to track down hotels/resorts where you can all have plenty of room to stay but also have your own "con suite", event room, private dining area. But they can also find "serviced" vacation homes/compounds/resort villas that include cleaning staff and catering (usually 2 meals a day where you're on your own/kitchen is stocked for self-serve breakfast or lunch).
posted by Lyn Never at 11:59 AM on July 23, 2023 [2 favorites]


Also consider Disney and any resort that offers a destination wedding. Your catered Christmas dinner would look awfully similar to a wedding rehearsal dinner.
posted by shock muppet at 12:34 PM on July 23, 2023


Response by poster: For headcount, looking at 8 adults, 5 kids. Would need at least four "bedrooms" or sleeping spaces. If anyone has any specific recos of names of resorts, lodging, hotels, etc, would appreciate it.
posted by dede at 12:47 PM on July 23, 2023


My wife's family did a multi-generational trip at Iberostar ParaĆ­so Maya and everyone enjoyed it. It's basically a cruise that doesn't go anywhere - all inclusive, lots of dining options, kid's club, etc.
posted by Mid at 2:09 PM on July 23, 2023


Google maps does say that Iberostar Paraiso Maya is adults-only though....
posted by Windopaene at 2:40 PM on July 23, 2023


There are 4 or so hotels on the same site under the Iberostar name - I think they share some pools etc. I probably linked the one with no kids, but there are definitely kid-friendly parts of the resort.
posted by Mid at 2:55 PM on July 23, 2023 [1 favorite]


I eventually saw that there were several, my bad.

And you are then in the Yucatan, with all those cool pyramids for day trips. If I wasn't afraid to go to Mexico right now, this would be high on my list...
posted by Windopaene at 3:08 PM on July 23, 2023


an all inclusive is a great idea, we have stayed at the Iberostar mentioned above with a group of 12 (3 families of 4) and it worked out great. There wouldn't be one indoor space that everyone could hang out in that i know of, but lots of outdoor spaces.

The Fives could be a great option. We went right after it opened, so i think it has expanded dining options now, but there are 1, 2 and three bedroom condos plus all inclusive options. Beautiful. Our one bedroom had enough room for many people to hang out, so i am sure the larger condos would have plenty as well. each family could get their own residence.

The only hiccup possibly with all inclusives is sometimes it is hard for you all to sit together at dinner with a large group.

When i was young and we travelled with other families to go skiing or something, each family would get their own condo in a building with common areas. Sometimes we would go out to eat, sometime there would be a group meal at one of the condos. worked pretty good and often the condo building would have a game room or something for kids to hang out together in.
posted by domino at 6:34 AM on July 24, 2023


enchantments in sedona (they might have other resorts in this chain too, very family friendly but not so kid-centered that it's obnoxious)
Dollywood? they have lots of different big ol
houses you can rent and get chef/cleaning serviced i think.

nthing ralk to a travel agent :) sounds like a fun trip!
posted by wowenthusiast at 7:05 PM on July 24, 2023


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