I generally have an idea of where I want to go, and I work in the travel industry so I ask colleagues but I also do a lot of looking on Tripadvisor. I also bookmark absolutely anything I see I like the look of, even if it’s only a photo of a place - you can use Tineye image search to find where they actually are. I watch a lot of travel shows too.
The last couple of years my adventures have started with the following questions - 1. Which countries can I get into with Covid restrictions and 2. Where can I get to on staff travel (as many flights are full and I travel on seats left over after fare paying passengers are on.) So although I have a lot of places on my bucket list, I am actually quite limited, but it’s a big world out there and it doesn’t stop us!
I would say do a lot of planning with the kids at the ages they are, and choose places based on their child-friendliness and whether you want to go there rather than whether you think your kids will remember it or value the experience. They are very young and will not remember much, but if planned and executed right they will grow up with a sense of adventure which will make your bigger and wilder adventures easier to engage them in.
I first took my kids somewhere a little more challenging when they were 8 and 5. We went to Rome, just the 3 of us as DH was working, and our return flight was cancelled due to a Air Traffic Control strike. The kids were beside themselves with worry that we would never get home, but I just booked us into a cheap hotel, and we got on the first flight next morning. No panic. We’ve since been left behind in Jordan, Mexico, Germany, and left DH behind in Australia, and we’ve spent many hours sitting in airports waiting for free seats. My kids take it all in their stride now and are quite happy to run the gauntlet of cheap flights if it means we have regular and exciting adventures. We also drive very long distances, and as long as we have good audiobooks and podcasts on hand that is fine too.
But you can’t just plop into the lifestyle of adventurous traveller with kids in tow, you have to train them up to it. So take all the opportunities you can to travel with them, and push it a little bit further each time. Eg when we went to Mexico, they had only ever stayed in a hotel or fancy campsite in a luxury plot, so we booked 3 days at each end of the holiday in an AI resort but the 8 days in the middle was in a cabana on the beach and we found a friendly local taxi driver who took us out and about each day. The kids loved the cabana much more than they liked the hotels, but they were there just in case the cabana was a disaster.
As a fellow family explorer but with older kids, I’m happy to give any advice I can. I love to get out and about more than most people do. 🤣