Scottsdale and the Phoenix area can be cold around that time of year. Or not. It just depends on the weather fronts. Florida is more reliably warm. However, a family friendly area with playgrounds and the like to push a stroller around is useful. Botanical gardens can be a nice place to push strollers outside and spend time with family. I think avoiding places that are excessively retirement oriented would be helpful. Toddler proofing a rental house could be a project, and a hotel with carpeting sounds easier to my mind. A resort with sitters available to hire could be quite a relief for parents.
Agree…bring a sitter or go somewhere there is babysitters like a cruise etc if the toddler needs to go on the vacation. Then the adults can go out to dinner and other vacation activities without having to plan around the baby.
I also recommend a cruise. On many lines, you can see as much or as little of the child as you want.
Another suggestion I haven’t seen here–San Juan. Yes, there are still some issues in Puerto Rico, but San Juan itself will be okay. The weather will be nice–warm enough to swim. You can pay for everything in US dollars. It’s cheaper than most mainland resorts. It’s exotic but safe. Like to gamble? Casinos are great.
And believe it or not…you can also feel great because you’ve helped an economy that genuinely needs help.
I’d pick a tropical climate and rent a home or condo that has a pool and a beach. When my parents celebrated their 40th anniversary, they rented a home in Barbados and besides my parents, there were my siblings and myself (3 married couples) and two just turned 4 year olds, two almost 2 year olds, and one infant. The house had its own pool. It was in walking distance to the beach. The house came with a staff and so they cooked the meals. There were also maids/caretakers who could help with watching the kids.
I’d go to a resort or on a cruise with kids programs so the parents can get a bit of a break. If that is not a big deal, rent a nice house someplace warm, maybe with a pool or oceanside. Toddlers love playing on a beach. It sounds like the baby will have lots of attention and people to help give his parents a bit of a break. Like they could go out for drinks after he’s asleep, knowing he’s safe and sound with the rest of you.
@soozievt
^ That’s the kind of thing we’ve had great luck with on multiple trips. The problem with staying in a hotel when traveling with family or friends is that it’s harder to just hang out together. Plus if you have small children in tow you have to either hire an unfamiliar babysitter or wait in restaurants with potentially overtired kids. If you have a house you can all gather in the living room and have dinner on your schedule. I agree that beachside and/or a pool is essential to making a warm weather trip feel like a true vacation.
Another thing that has worked for us-does either family have a house that might be attractive to use in a home exchange? We’ve gotten use of some great properties and it costs next to nothing.
I started traveling with my kids when they were 6 months. I am a Club Med fan - all inclusive with kids’ club. You could drop the toddler off for few hours if he is up for it or you could stay at the club with him because they would have many toys and activities to entertain him (with someone in the room with him). With a toddler it would be easier to stay at one place instead of moving around. With all inclusive, you could also eat whenever you want. Cruise is also a good option.
First few weeks of Jan should be a down time at most of those resorts before spring break.
Next year is going to be a milestone birthday for me. My kids asked where I wanted to go to celebrate. I told them the new Club Med at Punta Cana. My kids pretty much grew up at Club Med, so it will be nice. The difference this time is I don’t plan on paying. 
My whole extended family will be there too.
Which coast is the toddler traveling from? I agree with the thought that helping the little one stay in a close time zone is a good one, but then again my 19 mo old granddaughter did ok traveling all over the place, so its a consideration but may not need to be a major one.
Are you trying to find a place that requires some reasonable fairness in travel for both coast travelers? If you are looking for beach options without leaving the states, there are several good options on the gulf ( in TX, ALA, FL). If you want FL, a very adorable place is Anna Maria Island. Quaint, less expensive, less “touristy”.
Any where in the US may be cold in Jan. You would need to go much further down south to get some warm weather.
HaHa! This reminds me of when my S was about that age and I started taking him to our local library for story time; the first week he was squirmy and cranky, and after a while I took him out. The next time we went back, he was equally squirmy and cranky and this time the story-teller stopped and came over to speak with me - she asked me to leave and never bring him back, LOL! We never did go back and I don’t think I ever took him to another library story time!
Instead of mapping out libraries, I used to map out parks with swing sets. My kids always needed few hours of park time. I used to be able to keep them quiet if I told them we were going to a park later on.
To me, this is when a cruise can be a perfect multi-generational cruise. Plenty of down time for the toddler and plenty of grown up time for the others. Food tastes and eating times are all covered; housekeeping; entertainment for all; pools to swim in; gorgeous/fun/relaxing ports of call (Eastern Caribbean is wonderful); overall costs are reasonable.
Sailed when mine was a toddler and have done numerous with nephews of all ages and family of all ages! EVERYONE still talks about how fun it was.
I only have two thoughts to put out there-
- Take into account what mode of transportation the family with the toddler will have to take. If a flight make it just one.
- Stay somewhere that the toddler can nap yet the parents aren’t stuck in the room with the napping child. Even if it’s just two adjoining hotel rooms. I remember one trip with our S when he was a toddler. He needed a nap yet he couldn’t relax and fall asleep with us in the room. I was stuck sitting in the hotel bathroom. This is also helpful in the evening so the parents don’t have to miss out once the toddler goes to bed for the night.
Parks are great. My H and I were just in a city 2 hours from our house and we noted that when our kids were young that city was usually the first stop on our road trip drives. We would stop at the park and give them time to run around before getting back in the car. We noted that drives that now can be made with just one bathroom stop used to need at least 3 stops when the kids were young.
Update:
We are still in the researching mode but we have eliminated Scottsdale (or other continental US sites) and cruises are NOT for this group - did one years ago and none of the kids has any interest in another
We are now working through the pros and cons of all inclusive vs house rental in places where toddler can have direct or 1 stop flight (from SFO).
Thanks, all, for your help.
From SFO for a direct flight for the toddler a lot of people go to Cabo San Lucas. I haven’t been myself but I think it would hit most of your boxes.
SFO? There are zillions direct flights to Hawaii from Bay Area. Have you looked at that option? It will be a long travel day for the east coasters, but Hawaii is worth it.
I traveled with toddler twins once and it was a nightmare. They were 15 months old. One cried for hours after we arrived, didn’t sleep at all that first night. The other one was OK, but screamed for hours on the return trip. It cleared out a whole section of the airplane!
The hotel complex was busy and didn’t have the cribs they promised. We also didn’t have any car seats in the rental car. There was a big family group to help with them while we were there but nothing could help them cope with the travel portion. Children that age need to move, and confining them for hours in an airplane is difficult at best. They also are too young to understand that “we’re going to meet Grandma” and get excited about that.
My advice to people with babies is to live in a place that you really like, and have family come to you!
Seconding Hawaii if toddler is leaving from SFO. Go to a nice beachfront hotel with a kids club and babysitters.
Agree that the shorter the plane ride with with a toddler (or preferably none) the better. We always called that age unguided muscle and unless you have a nice mild mannered one, too long on a plane will be torture. Hawaii is still 5 hours from SFO. I would look for a drive or very short plane ride destination.
There are always a lot of little ones on flights between HNL and CA (both directions). Most of the time, it’s fine for everyone. I think our state would be an awesome destination. There are many houses for rent if you’d like to go that route or timeshares or hotels with adjoining rooms.
HI has something for everyone. Oahu has an excellent Children’s museums and most kids love the beach. Weather is predictably mild year round and T-shirt and shorts with a light jacket would be what many run around with during the day, perhaps with a hat & definitely sunglasses & sunscreen for the sun.