Looks like we have a time frame where we all can be free - early January, before grad student’s semester starts. No snow sports, prefer warmer climate. Open to exploring a new city to all-inclusive. Toddler will be 17 months old. Parties will be coming from both coasts.
Appreciate your suggestions.
Well frankly it really depends on the toddler. For mine the best vacation would have been… no vacation. They were big nappers and when their schedules were disrupted it was an unhappy time for everybody. But if we were going to go I’d say all inclusive anywhere with reliably good weather woukd have been my preference. That would have avoided some of the problems with a city kind of trip where you are moving around a lot, relying on transportation that can be tricky to navigate with any big group let alone a toddler. It’s also easier to run back to the room from group meals if need be or to have some go on an excursion while others chill at the resort where there may be simple activities for the toddler. Also I can’t think of any big cities in the US where it’s reliably warm enough to really enjoy the city other than in California or maybe Florida.
A lot depends on budget, ages of everyone, and what kind of things you like to do. Pricey, but I’m sure would be a hit with most - Atlantis/Paradise Island. On the flip side, nothing sexy but a lot cheaper - Charlotte. Great Wolf Lodge is much cheaper beginning of January vs Xmas and has a good sized airport for everyone. Outlets, if you like shopping, car racing - if you like that. We toured the Bronco’s stadium while in Denver and it was a highlight for us. I’m sure the Panther’s stadium does something similar. Tiger World is there - an educational/conservatory for exotic cats. If your little one likes trains, Spencer is 30-40 min away. Downtown Charlotte is really quite nice. We aren’t fancy people, but there are a lot of nice looking restaurants and stuff like that there as well. You’re near the mountains, and could probably find some good hiking, though one of my favorite area’s (Dupont Forest) is 2+ hours away and would be cold in January. An in between place, maybe the Tampa area? I don’t know much about it. We’ve looked at it before, but my friend’s 25 y.o. is there celebrating her 2nd honeymoon and I’ve seen pics of them on the beach and playing with penguins. 
And they also have a decent airport, I think. At least it’s one of the cheapest places for us to fly into…
Friends rented a condo on St. Simons Island. They weren’t looking for pizazz. They were looking to relax. IIRC, they had a three bedroom condo so each family had their own room. Two young children were there (under age 4). It was just a nice quiet family time.
I personally would prefer a rental home where you could potentially spread out and everyone - including parents/toddlers and others can have various options for spreading out instead of just one hotel room. As a mom with little ones, I would have also preferred the option of having a fair # of meals in the same spot - sort of keep a new temporary routine.
But it also depends on this toddlers temperament and the parents comfort level. Which brings me to the next suggestion which is to ask the parents of the toddler for some real input on what would make this vacation more “vacation” for them with a little one!
St. Petersburg Florida. You can rent a condo, airbnb, etc. You can stay on the beach at St. Pete Beach or Treasure Island and there are tons of places to explore within 15 to 30 minutes. Children’s museum in St. Petersburg, Seaside Seabird Sanctuary, Clearwater Aquarium with Hope and Winter the Dolphin, Primate Sanctuary, Boyd Hill Nature Preserve. City of St. Pete has museums, shops, vintage galleries, entertainment, Straub Park. It is a very walkable downtown area. The weather should be sunny and usually low 70’s, but there can also be a cooler snap of weather during that time. (high 50’s). Tampa airport is 30 minutes away and you can sometimes get great airfares.
I would not plan a vacation around a 17 m/o, at that age, they are more baby than toddler (IMO). The only planning I might do is to be mindful of where I eat and where I stay, i.ie if it’s more than a couple of days, make sure the accommodation has access to laundry facilities, and a pool might be nice; my kids liked a pool at that age. But in terms of kiddie activities ie zoos, museums etc, they could not care less…and make sure to have plenty of baby snacks and a few toys i.e. blocks on hand for toddler moments - other than that, have a GREAT time and enjoy!
I was going to say the same thing, @momo2x2018!
Thanks all.
Yes, the toddler will be 17 months old - with six adults to distract him, we’re not too worried about his needs. And it is hard to tell what he will be like 8 months from now, though so far he’s an easygoing guy.
Anyone spent time in Scottsdale? In January?
Well…I love the greater Phoenix area. You should be able to rent a house or condo. Lots to do in the greater Phoenix area…but not really for the 17 month old…
There are a few resorts in Scottsdale but I don’t know if any have suites, which might be nicer for you than just rooms.
Palm Springs? A house with a pool or the Westin or Marriott Vacation Club (condos) resort?
One suggestion for where ever you go. When traveling with a toddler, make a visit to the local public library. They have books, toys, programs (if you check the website before you go, mom and baby might be able to hit Story Time). It doesn’t sound like much, but to a toddler it is better than a theme park. It is great place for some calm time in the middle of the day. If you all are together the library offers moments of calm and privacy for the adults too.
One of kids favorite vacation memories is of a Story Time we happened into in a small town in Ohio. My kids must have been about 3 and 5. They still talk about “the Library with the crocodile puppets.”
At 3 and 5, kids are old enough to remember some things. But story time for a baby 17 months old? I would not center my vacation around a library visit.
Cruises in the Caribbean are nice that time of year. Kind of allows everyone to do as much or as little as they feel like.
I agree with those who say not to worry about the toddler’s entertainment. The world is so new to them that they find anything entertaining. Book an airbnb, a condo, or a beach house, not a hotel. Do the activities that the adults want to do, but be mindful of the baby’s schedule. For example, we certainly went to museums when the kids were that little, but we made sure to time the visits so that they didn’t get worn out or cranky. We didn’t pick child friendly restaurants, necessarily, just restaurants that didn’t actively hate kids, and prepared for success by bringing things to entertain the kids and extra food in case the restaurant was slow or the food wasn’t suitable for a little child. As long as at least one adult is ready to take the child out if he gets upset or cranky or needs a nap, everyone can have a good time.
Drop off toddler with your in-laws and go somewhere. In a few years every vacation will be around school or sports schedules, summer stuff and college tours. Honestly. Do it.
Jet lag with that age really sucks so I’d stay in the toddler’s time zone if you get down to a couple of otherwise similar options (try talking a one year old into staying in bed quietly for an extra two hours because it’s 5am here even though it’s already 7am at home… ha ha ha).
OP isn’t asking how to plan the trip for the toddler’s entertainment, but just which warm weather January location might work out well. I agree with the idea of renting a house or condo in a resort area - maybe Sanibel-Captiva? January is so iffy in a lot of the country - I would suggest San Diego but it could be rainy. Another thought is San Antonio - not sure of the weather but we once stayed at Hyatt Hill Country and loved it.
When our youngest was 9 months old we rented a house in Mexico with friends that came with a cook/maid. It was great-eating fresh, local food professionally cooked at home was no more expensive than eating out and if we wanted to go out when the baby went down for a nap we could leave her behind with the maid. The Yucatan Peninsula is on Eastern Standard Time.
Editing to clarify-It was the house that came with staff, not the friends!
Captiva is perfect. Don’t stay at the south Sea Island. Beaucoup d’argent.
Tween Waters is better and nice. Or rent a house in the little downtown area. Make sure they have a golf cart to get around. Sanibel is nice to retire in but Captiva is a “go to” low key and quirky old Florida experience. It’s fabulous. And the gulf is swimable at that time of year. Sunsets are ridiculous.