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The weather in Tokyo is humid subtropical with hot humid summers and generally mild winters with cool spells. Annual rainfall averages nearly 1,530 mm, with a wetter summer and a drier winter. Snowfall is sporadic, but does occur almost annually.
All-weather gear. Throughout the year, be prepared for rainy and windy conditions. Ideal are lightweight hoodies like the highly weatherproof Arc'teryx Squamish jacket, which is breathable, too – handy for when the weather clears up again. Tuck a good (but compact) umbrella, like Repel's Windproof Travel Umbrella with Teflon Coating, into your bag, in case of a real downpour.
Super-comfy walking shoes. You will be doing a lot of walking in Tokyo, so the key is to be comfortable. Try to avoid bringing shoes you have not broken in. Tennis shoes (trainers, sneakers), hiking shoes or other types of durable sports shoes are probably your best bet. If you don't want to look like a tourist, dress fashionable! It might be a good idea to pack a not-too-bulky pair of trail runners, such as Saucony’s Peregrine 7 for men or women, that hold up well on wet and dry ground.
Power adapter and charger. In Japan the power sockets are of type A and B. The 2-pin plugs fit into North American sockets, but the voltage is different. The standard voltage is 100 V and the standard frequency is 50/60 Hz. Type A and B adapters are included in this world adapter set from Bestek, and a multiport charger, like Anker’s compact Powerport 4.
Packing cubes. They not only keep your suitcase organized, but also compact your clothes to save space. One of frequent travellers'favorites are Eagle Creek‘s Pack-It cubes, which come in different sizes so you can tailor your setup to your needs.
Travel guides. Lonely Planet has a great Tokyo travel guide. Spend all-night in a karaoke parlour in Shinjuku, walk the forest path to Tokyo's largest Shinto shrine, Meiji-jingu, or sample the delights of Mitsukoshi's food hall.
Other great sources of free information are the GoTokyo travel guide and Time Out Tokyo.