21 days in Japan Itinerary

Tokyo holds the status of most populous metropolitan area in the world--a fact you'll find tangible as you walk the bustling streets and explore its diverse neighborhoods and cultures.

Kick off your visit on the 1st (Tue): wander the streets of Ueno District. On the next day, get a sense of history and politics at Tokyo Metropolitan Government Buildings, make a trip to Meiji Jingu Shrine, then take in panoramic vistas at Tokyo International Airport International Terminal Observation Deck, and finally take in panoramic vistas at Tokyo International Airport (Haneda) Terminal No2 Observation Deck.

To find reviews, photos, more things to do, and more tourist information, refer to the Tokyo trip builder site.

Boston, USA to Tokyo is an approximately 17.5-hour flight. Traveling from Boston to Tokyo, you'll lose 14 hours due to the time zone difference. In October, Tokyo is somewhat warmer than Boston - with highs of 72°F and lows of 60°F. Finish your sightseeing early on the 3rd (Thu) to allow enough time to fly to Shari-cho.

Tourism in Shari-cho, a small town situated on Hokkaido's eastern tip, flourishes mainly because of its immediate proximity to the Shiretoko World Heritage Site.

On the 4th (Fri), take a memorable drive along Road to Heaven, then contemplate the waterfront views at Shiretoko Goko Lake, then admire the sheer force of Kamuiwakka Hot Waterfall, and finally walk around Pereke River Shore Park.

To see ratings, other places to visit, more things to do, and other tourist information, read Shari-cho vacation planner.

You can fly from Tokyo to Shari-cho in 3.5 hours. Other options are to take a train; or drive. Prepare for slightly colder weather when traveling from Tokyo in October: high temperatures in Shari-cho hover around 57°F and lows are around 46°F. Finish your sightseeing early on the 4th (Fri) so you can fly to Miyakojima.

A city jurisdiction formed after the merger of several towns in 2005, Miyakojima spans six linked-up islands.

Step off the beaten path and head to East Henna Cape and Sunayama Beach. Next up on the itinerary: kick back and relax at Aragusuku Beach, take in the views from Kurima Bridge, get outside with Yonaha Maehama Beach, and make a trip to Ikema Ohashi Bridge.

To see maps, more things to do, traveler tips, and other tourist information, read our Miyakojima holiday builder website.

Fly from Shari-cho to Miyakojima in 7 hours. Expect much hotter temperatures when traveling from Shari-cho in October; daily highs in Miyakojima reach 83°F and lows reach 75°F. Wrap up your sightseeing on the 7th (Mon) to allow time to travel to Iriomote-jima.

Taketomicho Iriomote-Jima stands as the second largest island in Okinawa.

Kick off your visit on the 8th (Tue): skim along the rocks with a canyoning and rapelling tour and then take a tour by water with Boat Tours & Water Sports. Get ready for a full day of sightseeing on the 9th (Wed): take in the dramatic scenery at Mizuochi Falls, identify plant and animal life at Funauki Village, then step off the mainland to explore Iriomote Island, and finally take in the dramatic scenery at Pinaisara Falls.

To find ratings, maps, more things to do, and other tourist information, refer to the Iriomote-jima journey builder app.

Traveling by combination of flight and ferry from Miyakojima to Iriomote-jima takes 4 hours. October in Iriomote-jima sees daily highs of 85°F and lows of 76°F at night. Finish your sightseeing early on the 9th (Wed) so you can ride a ferry to Ishigaki.

Ishigaki, the most populous island in the chain, features the country's southernmost city and acts as a transport hub for exploring the landmasses that surround.

You'll discover tucked-away gems like Yonehara Beach and Cape Hirakubozaki. The adventure continues: glide peacefully along the water with some of the best stand-up paddleboarding in the area, take a leisurely stroll along Nishi Pier, enjoy breathtaking views from Maesedake Observation Site, and kick back and relax at Kondoi Beach.

To find traveler tips, maps, and other tourist information, refer to the Ishigaki trip itinerary planning app.

You can ride a ferry from Iriomote-jima to Ishigaki in 1.5 hours. In October, daytime highs in Ishigaki are 85°F, while nighttime lows are 76°F. Wrap up your sightseeing on the 12th (Sat) early enough to travel to Takachiho-cho.

The mountain town of Takachiho-cho remains a place of great importance to Japan's spiritual and natural heritage, and the point where these two things intersect.

Start off your visit on the 13th (Sun): go for a walk through Amano Yasugawara, contemplate in the serene atmosphere at Amano Iwato Shrine, take in the spiritual surroundings of Kaguraden, then contemplate in the serene atmosphere at Takachiho Shrine, then explore the stunning scenery at Takachiho Gorge, and finally contemplate in the serene atmosphere at Amanomanai.

Before you visit Takachiho-cho, use our trip planner to discover what you can do and see there.

You can do a combination of flight and bus from Ishigaki to Takachiho-cho in 8 hours. Traveling from Ishigaki in October, expect Takachiho-cho to be little chillier, temps between 75°F and 59°F. Finish up your sightseeing early on the 13th (Sun) so you can travel to Hiroshima.

Grapple with history and appreciate modernity in Hiroshima, a city known around the world for its tragic past and inspiring rebirth.

Start off your visit on the 14th (Mon): catch a live event at MAZDA Zoom-Zoom Stadium Hiroshima, pause for some photo ops at Memorial Tower to the Mobilized Students, then contemplate the long history of Atomic Bomb Dome, then appreciate the history behind Peace Bell, and finally steep yourself in history at Peace Memorial Park - Hiroshima. Here are some ideas for day two: get outside with Mikasahama Beach, step off the mainland to explore Miyajima, and then contemplate the long history of Itsukushima Shrine.

For traveler tips, other places to visit, and tourist information, read our Hiroshima road trip site.

Do a combination of taxi and train from Takachiho-cho to Hiroshima in 5 hours. Alternatively, you can do a combination of bus and train; or drive. Expect a daytime high around 73°F in October, and nighttime lows around 61°F. Wrap up your sightseeing on the 15th (Tue) to allow time to take a train to Kyoto.

The national capital for over a thousand years, Kyoto retains much of the charm of old Japan, boasting numerous temples and shrines that seem completely untouched by the modern world.

On the 16th (Wed), contemplate the long history of Kiyomizu-dera Temple, then contemplate in the serene atmosphere at Kodai-ji Temple, then contemplate in the serene atmosphere at Nanzen-ji Temple, and finally don't miss a visit to Eikando Zenrinji Temple. Get ready for a full day of sightseeing on the next day: take in the spiritual surroundings of Tofuku-ji Temple, steep yourself in history at Fushimi Inari-taisha Shrine, and then take in the spiritual surroundings of Tenryuji Temple.

To see other places to visit, maps, traveler tips, and tourist information, refer to the Kyoto day trip planning app.

You can take a train from Hiroshima to Kyoto in 2.5 hours. Alternatively, you can drive; or do a combination of bus and train. In October in Kyoto, expect temperatures between 74°F during the day and 60°F at night. Wrap up your sightseeing on the 17th (Thu) early enough to take a train to Maihama.

You've now added Tokyo Disneyland to your itinerary. Kick off your visit on the 18th (Fri): make an unforgettable trip to Tokyo Disneyland. On the 19th (Sat), you'll have a packed day of sightseeing: get in on the family fun at Funabashi Andersen Park and then make an unforgettable trip to Tokyo DisneySea.

For ratings, more things to do, other places to visit, and more tourist information, read Maihama trip itinerary builder.

Take a train from Kyoto to Maihama in 3 hours. Alternatively, you can do a combination of flight and bus; or drive. In October, plan for daily highs up to 70°F, and evening lows to 65°F. Wrap up your sightseeing by early afternoon on the 20th (Sun) to allow time for travel back home.