14 days in Japan Itinerary

14 days in Japan Itinerary

Created using Inspirock Japan visit planner

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Route & dates

Start: Boston
Fly:  21 h 30 min
1
Ishigaki
— 2 nights
Ferry:  1 h
2
Iriomote-jima
— 1 night
Ferry:  4 h
3
Miyakojima
— 2 nights
Fly:  5 h 15 min
4
Kyoto
— 3 nights
Train:  2 h 30 min
5
Tokyo
— 4 nights
Train + Fly:  17 h 30 min
End: Boston

2
nights
Ishigaki

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.
Start off your visit on the 1st (Thu): take in panoramic vistas at Tamatorizaki Observatory, then visit a coastal fixture at Cape Hirakubozaki, then take a tour by water with Boat Tours & Water Sports, and finally enjoy the sand and surf at Kondoi Beach. Keep things going the next day: add some adventure to your tour with a kayaking and canoeing tour, get outside with Yonehara Beach, and then identify plant and animal life at Wildlife Areas.

To see photos, maps, where to stay, and tourist information, you can read our Ishigaki trip itinerary planner.

Boston, USA to Ishigaki is an approximately 21.5- hour flight. You can also do a combination of train, tram, and flight; or do a combination of train and flight. Traveling from Boston to Ishigaki, you'll lose 14 hours due to the time zone difference. Expect a bit warmer temperatures when traveling from Boston in September; daily highs in Ishigaki reach 89°F and lows reach 79°F. Wrap up your sightseeing on the 2nd (Fri) early enough to ride a ferry to Iriomote-jima.

Things to do in Ishigaki

Outdoors Tours Adventure

Side Trip

Kondoi Beach
Find places to stay Sep 30 — Oct 2:
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Cape Hirakubozaki ©
Cape Hirakubozaki
Kondoi Beach ©
Kondoi Beach
Scuba & Snorkeling

1
night
Iriomote-jima

Iriomote-jima ©
Taketomicho Iriomote-Jima stands as the second largest island in Okinawa.
Start off your visit on the 3rd (Sat): step off the mainland to explore Iriomote Island, kick back and relax at Hoshisuna Beach, and then glide peacefully along the water with categoryPhrases.alias.some_of_the_best_stand_up_paddleboarding_in_the_area.

For reviews, ratings, photos, and tourist information, read our Iriomote-jima trip itinerary builder website.

You can ride a ferry from Ishigaki to Iriomote-jima in an hour. In October in Iriomote-jima, expect temperatures between 85°F during the day and 76°F at night. Finish your sightseeing early on the 3rd (Sat) so you can ride a ferry to Miyakojima.

Things to do in Iriomote-jima

Outdoors Tours Adventure
Find places to stay Oct 2 — 3:
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Hoshisuna Beach ©
Hoshisuna Beach
Iriomote Island ©
Iriomote Island

2
nights
Miyakojima

Miyakojima
A city jurisdiction formed after the merger of several towns in 2005, Miyakojima spans six linked-up islands.
Start off your visit on the 4th (Sun): explore the gorgeous colors at Yabiji, kick back and relax at Sunayama Beach, add some adventure to your tour with a kayaking and canoeing tour, then enjoy the sand and surf at Yonaha Maehama Beach, and finally enjoy the sand and surf at Aragusuku Beach. Here are some ideas for day two: head off the coast to Shimojiiima Island, then enjoy the sand and surf at Toguchi no Hama, then take in the views from Irabu Ohashi, and finally take a tour by water with Boat Tours & Water Sports.

For where to stay, more things to do, reviews, and more tourist information, read Miyakojima trip planning tool.

Traveling by ferry from Iriomote-jima to Miyakojima takes 4 hours. October in Miyakojima sees daily highs of 83°F and lows of 75°F at night. Finish up your sightseeing early on the 5th (Mon) so you can travel to Kyoto.

Things to do in Miyakojima

Outdoors Parks Beaches
Find places to stay Oct 3 — 5:
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Yabiji
Yabiji
Scuba & Snorkeling
Sunayama Beach ©
Sunayama Beach

3
nights
Kyoto

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.
Your inner history buff will appreciate Fushimi Inari-taisha Shrine and Eikando Zenrinji Temple. You'll discover tucked-away gems like Kodai-ji Temple and Asahiyaki. Go for a jaunt from Kyoto to Dotombori to see Dotombori District about 1h 10 min away. Next up on the itinerary: don't miss a visit to Nijo Castle, hunt for treasures at Nishiki Market Shopping District, take in the spiritual surroundings of Kinkaku-ji, and contemplate the long history of Kiyomizu-dera Temple.

To find traveler tips, reviews, other places to visit, and more tourist information, read our Kyoto day trip app.

You can fly from Miyakojima to Kyoto in 5.5 hours. Alternatively, you can do a combination of flight, tram, and train; or do a combination of flight, bus, and train. In October, Kyoto is a bit cooler than Miyakojima - with highs of 74°F and lows of 60°F. Cap off your sightseeing on the 8th (Thu) early enough to catch the train to Tokyo.

Things to do in Kyoto

Historic Sites Neighborhoods Shopping

Side Trips

Osaka, Asahiyaki
Find places to stay Oct 5 — 8:
Highlights from your plan
Nijo Castle ©
Nijo Castle
Kiyomizu-dera Temple ©
Kiyomizu-dera Temple
Fushimi Inari-taisha Shrine ©
Fushimi Inari-taisha Shrine

4
nights
Tokyo

Tokyo ©
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.
Let the collections at Pola Museum of Art and Tokyo National Museum capture your imagination. Your cultural itinerary includes sights like Samurai Museum and Hakone Shrine / Kuzuryu Shrine Singu. Get out of town with these interesting Tokyo side-trips: Gotemba Premium Outlets (in Gotemba) and Yokohama Museum of Art (in Minatomirai). And it doesn't end there: contemplate in the serene atmosphere at Senso-ji Temple, stop by Odaiba District, make a trip to Takeshita Street, and see the interesting displays at Edo-Tokyo Museum.

To see photos, where to stay, maps, and other tourist information, go to the Tokyo journey planner.

You can take a train from Kyoto to Tokyo in 2.5 hours. Alternatively, you can fly; or drive. In October in Tokyo, expect temperatures between 72°F during the day and 60°F at night. Wrap up your sightseeing on the 12th (Mon) early enough to travel back home.

Things to do in Tokyo

Neighborhoods Museums Shopping

Side Trips

Hakone-machi, Gotemba Premium Outlets, Yokohama Museum of Art
Find places to stay Oct 8 — 12:
Highlights from your plan
Ginza ©
Ginza
Pola Museum of Art ©
Pola Museum of Art
Hakone Shrine / Kuzuryu Shrine Singu ©
Hakone Shrine / Kuzuryu Shrine Singu

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