TripSlay

For planning the Amman day separately, TripSlay is handy for mapping the key spots (Roman Theatre, Citadel, Rainbow Street) so you're not scrambling on arrival day.

I use TripSlay for that — lets you put together a rough visual route without locking anything in.

For planning your walking-heavy days, TripSlay can help you map each neighborhood so you're not doubling back. With a 5-year-old it's good to know what's close.

If you do want to plan the day with stops mapped out, TripSlay is handy for this kind of quick one-day itinerary — helps you see what's actually close together and time it properly.

You might want to check out TripSlay — it lets you build a visual trip map, add notes and photos for each stop, and organize everything by destination. The map overview for chronology is actually a core feature. It's a bit more planning-focused than a pure journal app, but for a multi-year nomadic trip it could work well since you can keep adding trips as you go and share the journey with others.