I'm pretty sure Rita's name is Irma

Hawai'i would certainly be warmer, but as jamie noted it might be a bit late to get good lodging or airfare deals. Then again, it's always worth a try. Food's great, you can get good wine (but you'll pay for it), it certainly has history and culture, and you can't swing a musubi roll without hitting the ocean (well, maybe a bit harder in the center of Big Island).

Puerto Rico might get walloped real bad by Irma, but by Xmas time they might be up and running fine and begging for visitors. Depending on the paths of any more of those damn hurricanes...!

East Coast options might be cheaper than West Coast warm spots. I'm thinking specifically of New Orleans (OK, it's Gulf, not ocean, it's on, but it's water, ain't it?!), Savannah and Charleston. Food's good in all of them (especially New Orleans, and I'm not saying that just because I'm Creole), again you can find good wine (not "local", and you'll pay for it, but they have good wine sources), the history is unique. A lot will hinge, again, on if Irma and any other hurricanes wreak lasting damage to these places.

West Coast? LA is still a very popular tourist destination over Xmas/Hanukkah holidays, as is San Diego. Santa Barbara sits a bit north of LA and flies under many tourists' radar, but it ticks just about every box: history, great food and wine (AWESOME wines in and near this southern-edge-of-Central-Coast town), culture (nice museums, performing arts venues, music, etc.), and lovely stretches of the Pacific. I might recommend looking at places like Carlsbad or Laguna Beach; both have their attractions. Yeah, Palm Springs is well inland, but it can be fun for a couple of days. You might think about splitting your time between LA or San Diego and PS. Just a thought.

I'd also, with an understanding that it will be quite cool there, recommend without hesitation a holiday in San Francisco. In a New York minute. Wonderful place. But you know that already.

I am hoping my husband and I can get up to Fort Bragg to celebrate the holidays with family living up there. That part of the coast is quiet and extremely laid-back and boasts coastlines of stark beauty and terrifying sheer drops (sections of Highway 1 through this area is NOT for the faint-hearted or weak-stomached). The wineries of the Anderson Valley produce world-class pinot noirs (seriously some of my favorite wine comes out of Philo), and you can find some incredible restaurants hidden away up there. Culture? OK, a bit small-town, full of aging hippies (I'm not judging, I'm just calling it like it is-- "stoners in late middle-age" describes a lot of my best friends!). You go there to get away from it all, but still have electricity (most of the time) and occasional cell-phone service (but not good and fairly infrequently).

Seattle would be on my list too. Although it's "high" up north, its weather isn't quite as dramatic as Chicago's, and hey-- it's a hotbed of great food, wine and culture. As is Portland.

Actually, now that I think of it, your interest in good food and wine would have me pointing you to the West Coast, cool weather be damned. Start looking now. Look at the southern cities (West or East Coasts) if being warmer is really that important.

The problem with Seattle in December is it is DARK... not the weather so much. Because of being so far north the days are extremely short. Like sunset at 4:15 or so!!

We spend a many Christmas to New Years in Key West. It is just a great time of year to be there. The lights are tacky and fun and beautiful. I love the Dachshund parade on NYE day. Rent a house in Truman annex for the week. Some come with bikes but you can walk to everything from that area easy. Great food, sunset sails, fun and warm. Once you fly into KW take a taxi to your home for the week. No car needed.

I've done Hawaii during Christmas/New Year's a few times, but they were more serious relaxing trips than anything else.

I've also done La Jolla/San Diego and Rancho Mirage. Weather was lovely. Many heated pools. Plenty to see and do.

I have friends who adore certain beaches of Mexico at the holidays.

If you can do without ocean, I think Santa Fe would be a great option and something quite different from what you have done in the past. The city is famous for its luminarias or "farolitos" during the holiday season. Below a link to a faralito walk on Canyon Road. The walk is free but you can also take a guided tour.
www.farolitowalk.com.

Although this was topped off by a spammy post, it is interesting to read the destination suggestions from early September, along with the

Puerto Rico? That's a no.
USVI? My cousin who lives there is at 94 days without power still.
San Diego/Southern California? An inferno. A friend of mine from Ventura is having to sleep on the beach with embers dropping on them.

This has been a year of disasters, natural and otherwise. :'(

Oh man, sludick. I was watching the footage from the Ventura fire and it’s just so scary. Feeling fortunate that I did not plan my Christmas trip for San Diego as I had originally been considering. Hope your cousin and friend have suitable shelter soon! I can’t imagine what they must be feeling.