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where should we go for a month with two little kids?

We’re a Canadian family of four, and we’re itching to take a month-long break somewhere warm next winter. The plan is to go during my parental leave, so we’ll have a 3-year-old and a 6-month-old in tow—plus the stroller, diaper bags, and all the chaos that comes with traveling with little ones. We’ve already done a lot of the US, and honestly, the Canadian dollar just doesn’t stretch far enough there for a whole month. I keep dreaming about waking up somewhere sunny, maybe walking to a cozy coffee shop while the kids nap in the stroller, and finding parks that are actually safe and clean. But every time I start searching, I get overwhelmed by the options. Some places look great online, but then you find out the sidewalks are a nightmare for strollers, or the Airbnbs are miles from anything interesting. And let’s be real—if I can’t get a decent cup of coffee or a quick meal nearby, I’m going to lose my mind after a week. Has anyone found a spot outside the US that’s actually stroller-friendly, has good Airbnbs, and doesn’t make you feel like you’re stranded in the middle of nowhere with two cranky kids? I’m hoping there’s a hidden gem out there, but maybe I’m just dreaming. We want warmth, walkability, and some sanity-saving amenities. If you’ve been somewhere that checks these boxes (or you’ve had a disaster trip and want to warn us), I’d love to hear about it. Traveling with kids is hard enough—finding the right place shouldn’t be another headache! #familytravel #parentalleave #travelwithkids #Travel

2025-05-30
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