10/13/2026
AI can suggest cities, organize your wish list, and give you a starting itinerary.
But there’s a difference between reading about a place and walking through it while thinking about the family you’re planning for.
In Florence, I noticed the narrow sidewalks where a family might have to walk single file. The moments you step into the street to get around people, and suddenly a car or bike is right beside you. The crowds, the walking, and how another museum day might feel to a 10-year-old who’s already spent days sightseeing in Rome.
Those details helped me ask a different question: would this family enjoy a day in Florence—or would they be happier relaxing together at their Tuscany villa?
After talking it through with his mom, we left the day open.
AI can be a great place to start. But it can’t replace the relationship with someone who listens, knows your family, and brings firsthand experience to the decisions you make together.
Save this for your next trip, share it with your travel partner, and follow for thoughtful travel planning that goes beyond the itinerary.
