My daughter (8) and I are back to WDW in December. This will be our second trip after a fabulous first in May 2019. I’m happy to be a part of this awesome community again as we officially start planning for the trip. Our first night (a sunday) we will be arriving and needing dinner. We will be staying at Pop Century in order to be close to the skyliner. Are there any outdoor restaurants on the skyliner that you suggest? Table or quick service are ok as long as outdoor. We’re open to Boardwalk or a hotel. We can also lyft to Disney Springs if that might be a better food choice. We’ve never been to any of these locations during the holidays so if there’s a particularly good spot for holiday cheer that would be appreciated too. We plan to eat quick service in the parks the following nights so this is our only night to explore something different. My daughter is an adventurous eater 
Thanks!
Boathouse at DS. Great view outside.
Nice. Thanks!
Is Boardwalk not really worth going to? We didn’t go last time.
We’ve also never been to Beaches and Cream and have heard awesome things about them here.
We’ve gone there twice for the kitchen sink. If y’all love ice cream, it’s a fun experience just from the sheer indulgence. But there is nothing special about the ice cream itself. And we still haven’t bothered with a meal there.
You might also consider getting to-go from a TS and eating somewhere out on the boardwalk if they don’t have outside dining. That would open up more options depending on what your daughter likes. (My kids have always been pretty adventurous eaters too.)
For instance, my kids love mussels, so To Go from Trattoria al Forno could be awesome. (I haven’t been, but hear such good things.) I also have Ale & Compass on my list to try.
You might want to keep eating inside as a consideration. Nights in December aren’t always comfortable… I’ve had a few where they’re down right frigid.
Yeah, that was part of my thinking on “To Go”. They could always pivot and take it back to their room if it’s too cold and would at least get to look around the boardwalk a bit.
Is there anyplace good on the boardwalk that has outside dining with heaters?
These all make sense. We’re coming from New England so shouldn’t be too cold for us. But yes, outdoor heaters would be ideal. We’re trying to avoid eating indoors for safety reasons. @amvanhoose_701479 that’s good to know about Beaches and Cream. My daughter isn’t a sweets person so while it would be fun if the food isn’t all that good then we might skip.
I was also looking at some of the Riviera resort restaurants as an option. A nice sit down meal (TS) would be fine with us and they seem to have some options. I just don’t know if they will let you make outdoor seating reservations. Has anyone had success here?
The restaurants that have outdoor seating do not make ADRs just for outdoor tables. They won’t guarantee them. But when you check in you can request an outdoor table. You might have to wait to sit outside but you can make the request
Topolino’s has an outdoor patio area. A year ago I called to see if they would seat people out there for full TS. They said they would.
But honestly people have had hit or miss experiences with spaces like those that are not in the typical seating charts of the restaurants.
Sorry the list linked to above does not have Swan and Dolphin (also skyliner adjascent) because I believe there a couple of places with outdoor seating there.
But there is a link in that forum to the WDWDining restaurant search. You could filter for DS or Swan and Dolphin and then look at their descriptions to see which offers outdoor seating - a really nice feature of their descriptions.
I don’t know the culinary preferences of your eight year old, but I’d consider something as simple as pizza from the window on the boardwalk. Also, primo patio from the Riviera is also meant to be very good. And I’m sure you could pick it up and take it outside somewhere to eat. I like the landscaping there.
Bar Riva is open air right by the pool at Riviera. No other outdoor options really unless you want to get QS and take it outside. The wings are excellent at Bar Riva though!
Wine Bar George at DS has outdoor areas with heaters, and a kid’s menu! You might also be interested in trying the small plates with her, since they are adventurous but more reasonable portions (plus who doesn’t like fried mac and cheese balls!). Myself and a few friends (all from Mass or VT) ate out there on a chilly night in February and were comfortable… until we got the wine slushies!
Yeah, you’d think, but I’m originally from northern Minnesota so am use to adjusting to that level of cold, and Florida can be a little surprising. On our 1 week trip in Jan 2020, we were shivering and thankful to have gloves one morning at rope drop at the beginning of the week when it was in the 40s with high wet and cold humidity, and wearing shorts at the end when the highs were in the mid 80s. It’s really a dice roll what you’re going to get. And sunset will be early in December. I mean, it doesn’t get crazy cold, but can be not pleasant for impromptu outside dining even for those used to cold.
All of the resorts and the boardwalk should be decked out for the holidays. Personally, I prefer those atmospheres to Disney Springs.
I’m very food-centric (I haz award!) so if it was me and DD20 back when she was that age, I’d look through the following menus and see which you think she’d enjoy the most. (Some I’ve been to and others I’ve heard great things about.)
Geyser Point at Wilderness Lodge - Lounge with outdoor seating. If it were me doing this one on arrival day, I’d take the bus to Magic Kingdom to catch a glimpse of the castle from outside the park as a “teaser”, and then take a ferry to Wilderness Lodge (my kids love the ferries). Then, I’d probably take a rideshare back to Pop after just for convenience (but you could just go back the same route you came). There is a virtual waitlist that you can join once you get close enough, and then you can wander around the resort while you wait. The main lodge is gorgeous. Depending on how much time you have, you could also do a monorail tour from MK to look at some of the other resorts. (Does anyone know if they have heaters if it’s chilly?)
Captain Cook’s at Polynesian - QS with outside seating, but it has a more interesting menu than most QS. Same transportation plan as Geyser Point, except you can ferry or monorail from MK. Mobile ordering available.
Kona TS To Go at Polynesian - you can use the Captain Cook’s outside seating
Three Bridges at Coronado Springs - Open air “casual dining”. Virtual waitlist (no reservations). You’d probably want to rideshare to/from. (Does anyone know if they have heaters if it’s chilly?)
Ale & Compass To Go at Yacht Club or Trattoria as Forno to Go at Boardwalk- find a place to eat on the boardwalk if the weather is favorable
For all the “To Go” menus, they may vary slightly from the full TS menus. You can access the actual To Go menu through the Disney app during the hours that “To Go” is offered so you can see what is available. Just tap “Order Food”, pick a time, and then cancel out when you’re done. (This also lets you see pictures for most menu items.)
I grew up in MN too and winter is my favorite season; true story! Also, 32 degrees is 32 degrees no matter the latitude and requires mittens and jackets. Jan 2020 DDs and I were here and it dropped into low 40s… we bought REALL mittens in Canada… none of that Disney fake winter gear from Florida would cut it.
Yeah, we were really glad we still had our “Minnesota gloves” in our coat pockets from visiting there at Christmas. We have decent coats we take back and forth and then extra layers we store with family in MN!
I have some mittens that have suede palms, fur lined, that are great for driving. I’ve had them for over 40 years. 
Thanks so much to this link. I missed it when I was looking around for advice.
Thanks @debb13mc. We actually ate at Wine Bar George in 2019 because my daughter is obsessed with meat and cheese plates. It was really good but were thinking about trying something new.