14-day Tokyo-Osaka Itinerary (Autumn 2026) - Complete Japan Travel Guide

A balanced circuit of 14-day Tokyo-Osaka over 14-day: icons, gardens, backstreets, and bites.

Golden hours light temple facades—our route leans into late‑day views.

It’s grounded in real transit times and reliable rest windows.

We’ll keep detours in pocket: a café with modern roastery flair and a calm shrine when crowds swell.

You’ll start at 09:00 with tokyo cultural highlights tour in Tokyo, Japan.

Booking: No booking required.

Tip: Morning visits avoid crowds.

Midday brings at 14:00 with osaka in Osaka, Japan.

Booking: Advance booking recommended.

Tip: Afternoon is peak time.

Later at 18:00 with tokyo evening experience in Tokyo, Japan.

Booking: Dinner reservations recommended.

Tip: Evening is less crowded.

Wear broken‑in walking shoes to avoid blisters.

Carry a refillable water bottle; convenience stores will keep you topped up.

Tokyo-Osaka in autumn provides stunning fall colors and comfortable weather for extensive travel.

The cities offer different autumn experiences - from urban parks to traditional temple gardens.

Higher elevations change color first, so plan your route accordingly.

For multi-city trips like Tokyo-Osaka, book accommodations 3-6 months in advance, especially during peak seasons.

Consider using luggage forwarding services between cities to avoid carrying heavy bags on trains.

Many attractions require advance booking, particularly in Kyoto and Tokyo.