20 days in Japan Itinerary

20 days in Japan Itinerary

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Route & dates

20 days in Japan Itinerary

Start: Boston
Fly:  17​h 30​min
1
Tokyo
— 4 nights
train:  2​h 45​min
2
Kyoto
— 3 nights
train + Fly:  6​h
3
Ishigaki
— 1 night
ferry:  1​h
4
Iriomote-jima
— 4 nights
ferry:  4​h
5
Miyakojima
— 4 nights
Fly:  25​h
End: Boston

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.
Appreciate the collections at Tokyo National Museum and Edo-Tokyo Museum. Do some cultural sightseeing at Sensō-ji and The Hakone Open-Air Museum. Change things up with a short trip to Pola Museum of Art in Hakone-machi (about 2 hours away). And it doesn't end there: take a stroll through Odaiba, get a taste of the local shopping with Ginza, and make a trip to Takeshita Street.

To find traveler tips, photos, reviews, and other tourist information, read our Tokyo day trip planning site .

Boston, USA to Tokyo is an approximately 17.5-hour flight. You can also do a combination of flight and train; or do a combination of train and flight. The time zone difference when traveling from Boston to Tokyo is 14 hours. In October, Tokyo is somewhat warmer than Boston - with highs of 72°F and lows of 60°F. Wrap up your sightseeing by early afternoon on the 5th (Sat) to allow time for travel to Kyoto.

Things to do in Tokyo

Neighborhoods Museums Shopping

Side Trip

Hakone-machi
Find places to stay Oct 1 — 5:
Highlights from your plan
Pola Museum of Art ©
Pola Museum of Art
Tokyo National Museum ©
Tokyo National Museum
Edo-Tokyo Museum ©
Edo-Tokyo Museum

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.
Visit Gotemba Beach and Kaizu Osaki for some beach relaxation. You'll discover tucked-away gems like Kyoto Railway Museum and Nara National Museum. Step out of Kyoto to go to Obama and see Wakasa History Museum, which is approximately 1h 30 min away. There's much more to do: explore the historical opulence of Nijo Castle, take a stroll through Gion, contemplate the long history of Sanjusangendo Temple, and admire the masterpieces at Kyoto National Museum.

To plan Kyoto vacation without wasting time, ask Inspirock to design an itinerary.

You can take a train from Tokyo to Kyoto in 3 hours. Alternatively, you can fly; or drive. Expect a daytime high around 74°F in October, and nighttime lows around 60°F. Wrap up your sightseeing on the 8th (Tue) to allow time to travel to Ishigaki.

Things to do in Kyoto

Museums Historic Sites Neighborhoods

Side Trips

Gotemba Beach, Wakasa History Museum, Kaizu Osaki, Nara National Museum
Find places to stay Oct 5 — 8:
Highlights from your plan
Nijo Castle ©
Nijo Castle
Sanjusangendo Temple ©
Sanjusangendo Temple
Kyoto Railway Museum ©
Kyoto Railway Museum

1
night
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.
On the 9th (Wed), get to know the fascinating history of Island Countryside Settlement, then take a memorable drive along Nagurao Bridge, then explore the gorgeous colors at Kabira Ishizaki Manta Scramble, and finally take an in-depth tour of Ishigaki Yaima Village. Get ready for a full day of sightseeing on the next day: visit a coastal fixture at Cape Hirakubozaki, look for gifts at Yurateiku Market, and then kick back and relax at Kondoi Beach.

To find more things to do, maps, ratings, and tourist information, use the Ishigaki trip itinerary maker .

You can do a combination of train and flight from Kyoto to Ishigaki in 6 hours. Alternatively, you can fly. In October, Ishigaki is a bit warmer than Kyoto - with highs of 85°F and lows of 76°F. Wrap up your sightseeing on the 10th (Thu) to allow time to ride a ferry to Iriomote-jima.

Things to do in Ishigaki

Parks Outdoors Historic Sites

Side Trips

Island Countryside Settlement, Kondoi Beach
Find places to stay Oct 8 — 10:
Highlights from your plan
Cape Hirakubozaki ©
Cape Hirakubozaki
Kondoi Beach ©
Kondoi Beach
Island Countryside Settlement ©
Island Countryside Settlement

4
nights
Iriomote-jima

Iriomote-jima ©
Taketomicho Iriomote-Jima stands as the second largest island in Okinawa.
Escape the urban bustle at Canyoning & Rappelling Tours and Funauki Village. Discover out-of-the-way places like Scuba & Snorkeling and Nara no Taki Falls. There's lots more to do: tour the pleasant surroundings at Ida no Hama Beach, steep yourself in history at Wasurenaishi, admire all the interesting features of Utara Tanko, and take in the dramatic scenery at Mizuochi Falls.

Take the guesswork out of planning a Iriomote-jima vacation by using our trip itinerary maker.

Ride a ferry from Ishigaki to Iriomote-jima in an hour. In October, plan for daily highs up to 85°F, and evening lows to 76°F. Finish up your sightseeing early on the 14th (Mon) so you can catch the ferry to Miyakojima.

Things to do in Iriomote-jima

Outdoors Tours Parks
Find places to stay Oct 10 — 14:
Highlights from your plan
Hoshisuna Beach ©
Hoshisuna Beach
Funauki Village ©
Funauki Village
Mizuochi Falls ©
Mizuochi Falls

4
nights
Miyakojima

A city jurisdiction formed after the merger of several towns in 2005, Miyakojima spans six linked-up islands.
Discover out-of-the-way places like Aragusuku Beach and Hora Gyoko no Hama Beach. Your cultural itinerary includes sights like Higashi Hennazaki Lighthouse and Miyako Shrine. Next up on the itinerary: enjoy the sand and surf at Sunayama Beach, get outside with Outdoor Activities, tour the pleasant surroundings at Nagamahama Beach Coast, and don't miss a visit to Boraga Limestone Cave.

To find reviews, where to stay, more things to do, and tourist information, refer to the Miyakojima online trip maker .

Getting from Iriomote-jima to Miyakojima by ferry takes about 4 hours. Expect a daytime high around 83°F in October, and nighttime lows around 75°F. Wrap up your sightseeing on the 18th (Fri) to allow time to travel back home.

Things to do in Miyakojima

Outdoors Parks Beaches
Find places to stay Oct 14 — 18:
Highlights from your plan
Kayaking & Canoeing
Sunayama Beach ©
Sunayama Beach
Aragusuku Beach ©
Aragusuku Beach

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