Month Long Trip Feedback with 7 year old and 7 month old.

I am looking to plan a month long trip with my family; 2 adults - 7 year old and 7 month old May/June 2026. We are leaving from the states. Am I being too optimistic of this being fun/good time to travel? Will we be unhappy instead? Here are our tentative plans.

Arrive Croatia -

Dubrovnik - 5 nights

Split (or surrounding area) - 4 nights

Ljubljana - 5 nights

Dolomites - 4 nights

Venice - 2 nights

Tuscany - 5/6 nights

Amalfi - 3 nights

Naples - 1 night and leave

It sounds doable, but have not travelled with two kiddos yet. Is there another area that is recommended where we don't have to fly again once arriving?

Thanks in advance for feedback!