cartagena vs lisbon: which is better for a family trip?

I’m turning 40 soon, and I want to do something special with my family—a real trip, not just another weekend at home. We’ve already been all over the Caribbean, so I’m itching for somewhere new, but not so far that we spend half the week on a plane. I speak some Spanish, so I was eyeing Cartagena, but then everyone keeps raving about Portugal, especially Lisbon. Here’s the thing: my mom is pretty chill, but big, hectic cities stress her out. That rules out places like Rio or Medellin, which honestly sound exhausting just thinking about them. I want somewhere that feels safe and easy, but still has enough to do so we’re not bored after two days. Cartagena’s old city looks gorgeous, and I figured we could do some island hopping, but then I worry—is it too touristy? Will we get hassled everywhere we go? Lisbon seems more relaxed, but I don’t speak Portuguese (yet). I could probably pick up a few phrases by November, but I’m nervous about dragging my parents and my 6-year-old daughter around a city where we don’t know the language. Will we get by with English and a smile, or will we just end up lost and frustrated? And, honestly, as a Black family, I want to make sure we feel welcome wherever we go. I’ve heard mixed things about some places, and I don’t want to spend my birthday week feeling out of place. Has anyone done a trip like this—multi-generational, somewhere new, not too wild, but not boring either? Did you find Cartagena too chaotic, or Lisbon too hilly for older parents? Did you ever wish you’d picked somewhere else? I’m all ears for suggestions, especially if you’ve got a spot that’s friendly, interesting, and won’t break the bank. Sometimes I feel like I’m overthinking it, but I just want everyone to have a good time, not just me. #familytravel #cartagena #lisbon #Travel