Osaka and Kyoto 1-Week Itinerary SummaryA good breakdown is 2 days in Osaka and 4 in Kyoto. Kansai International Airport (KIX) is the most convenient airport to Osaka and Kyoto. A Japan Rail Pass is not a good idea for this itinerary, but a Kansai Thru Pass may be.
Kyoto is more relaxing. Tokyo is about 30% more expensive than Kyoto for travelers. If you prefer big cities, modern technology, nightlife and a huge selection of restaurants, Tokyo is for you. If you're after temples, shrines, garden, geisha and hiking, Kyoto is for you.
How long to spend in Osaka? Known for illuminated signboards, endless shopping arcades, its impressive castle and “the Kitchen of Japan,” spending 3 days in Osaka is the ideal amount of time to see most of the sights and eat most of the culinary delights this city has to offer.
You can visit Osaka at any time of year because the weather is temperate. The best times to visit Osaka are the fall (October/November) and spring (March/April/May). Summer (June/July/August) in Osaka is hot and humid. Winter (December/January/February) in Osaka is cold but not too cold for traveling.
Nara is 35 kilometers south of Kyoto City and about 28 kilometers east of Osaka. Thus, it's within easy day trip distances of these cities. Of course, if you want to slow down and enjoy Nara a bit more, it makes sense to stay a night in Nara to really explore the area.
As a weeb and history nerd interested in Japanese culture, both Osaka and Tokyo have a lot to offer. However, if you had to choose just one to visit first, Tokyo would be the recommended choice.
When traveling in Japan, especially if you're in one of the big cities such as Tokyo, Osaka, and Kyoto, you'll generally have no problem not speaking Japanese at all. There are usually English signs all over train stations and airports.