Start the day by reviewing the full city list and mapping realistic routes: cluster nearby cities (e.g., Melbourne-Sydney, Paris-Amsterdam-Brussels if you add Belgium later, or New York-Philadelphia-Boston) and mark primary airports and major rail hubs like London St Pancras, Paris Gare du Nord, and Tokyo/NRT or SIN for intercontinental connections. Use a travel app or spreadsheet to note visa requirements, typical transit times (flight vs. rail), and seasonal weather — for example, pack layers for Melbourne and Stockholm in December and expect mild, humid conditions in Singapore. Reserve any must-have intercity legs now (overnight trains, red-eye flights, or multi-city flight tickets) so the backbone of the trip is locked in before booking individual hotels and experiences.
Create an accommodations and transport plan by city: choose a central neighborhood in each place (CBD/Southbank in Melbourne, Le Marais in Paris, Mitte in Berlin, Downtown LA or Manhattan in New York) and reserve flexible bookings with free cancellation for the first nights to allow adjustments. Research and save one signature experience per city — for example, a Brighton day trip from London, a guided Seine cruise in Paris, a Chinatown food tour in Toronto, a tram ride and rooftop bar in Lisbon, and a rooftop dinner or show in Las Vegas — and block calendar slots so transit and rest are thoughtfully timed. Compile local transport passes (Opal in Sydney, OV-chipkaart in Amsterdam, Oyster or contactless in London, Octopus-equivalent in each city) and any cultural holidays or strike dates that could impact schedules.
Finish by building a prioritized list of attractions and dining picks for each city, balancing iconic highlights (Eiffel Tower, Acropolis if added later, Sydney Opera House, CN Tower) with neighborhood discoveries like Södermalm in Stockholm or the Marais in Paris; earmark a Michelin or highly rated local restaurant and a casual street-food spot for each place. Set alerts for fare drops and hotel deals overnight, and create a shared folder with scanned passports, travel insurance, booking confirmations, and emergency contacts accessible from mobile devices. Wind down by drafting a flexible 2-3 week sample route from your clusters (e.g., Australia block → Asia → Europe → North America) to visualize timing and ensure visa/entry requirements and seasonal weather make the sequence practical.