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Join Date: Sep 2009
Location: Minneapolis: DL DM charter 2.3MM
Programs: A3*Gold, SPG Plat, HyattDiamond, MarriottPP, LHW exAccess, ICI, Raffles Amb, NW PE MM, TWA Gold MM
Posts: 100,413
Don't try to do too much.
In terms of weather, Tokyo is often lovely at this time of year, with sunshine, highs of 55-60 F (no need for an outerwear coat in the afternoon), and beautiful fall leaves.
OTOH, Hong Kong can be surprisingly chilly with day after day of cold rain IME.