Morning flight from Dulles to Orlando; book nonstop if possible (IAD→MCO ~2.5 hrs) to maximize family time. Allow 2–3 hours at airport during holiday travel.
Collect a family-size rental (minivan or SUV) and check into your Orlando-area hotel or vacation rental, convenient to parks or Port Canaveral depending on plans.
Full day at Magic Kingdom to experience family rides, parades, and holiday decorations—buy Genie+ or Lightning Lane for better throughput during peak season.
Arrive in Orlando to position for cruise departures from Port Canaveral; shorter airport-to-port logistics than flying to Miami for eastern Caribbean sailings.