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🇯🇵 JAPAN 14–DAY ITINERARY (TOKYO ROUND-TRIP)

June 2027 • Tokyo → Kyoto → Kiso Valley → Matsumoto → Nagano → Kanazawa → Osaka → Koyasan → Tokyo
Travel Style: Temples • Mountains • Art • Craft • Fishing • Printmaking • Calm • Cultural Immersion
Car Rental: Days 5–9 (Nagiso → Kanazawa)

SECTION 1 — TRIP OVERVIEW

Travel Route Summary

Tokyo → Kyoto → Kiso Valley (Tsumago) → Matsumoto → Nagano → Kanazawa → Osaka → Koyasan → Tokyo

Arrival / Departure

  • Fly into: Tokyo (NRT or HND)

  • Fly home from: Tokyo (round-trip flights booked)

  • Trip Length: 14 days total (12 full days in Japan)

Total Themes

  • Sacred mountains

  • Edo-era towns

  • Tenkara fishing

  • Woodblock printmaking

  • Contemporary art

  • Zen temples

  • Great food

  • Quiet nature-driven experiences

SECTION 2 — DAY-BY-DAY ITINERARY

DAY 1 — Thu May 29

Fly Greenville → Tokyo
Long travel day. Rest, hydrate, sleep on plane if possible.

DAY 2 — Fri May 30

Arrive Tokyo → Shinkansen to Kyoto (Calm Arrival Day)

After landing:

  • Immigration, baggage, customs: ~1.5–2 hrs

  • Get cash (7-Eleven ATM)

  • Activate eSIM if needed

  • Follow signs to trains

Airport → Tokyo Station:

  • HND: Tokyo Monorail → Hamamatsucho → JR loop line to Tokyo

  • NRT: Narita Express (NEX) directly to Tokyo

Tokyo Station → Kyoto:

  • Tokaido Shinkansen: Nozomi or Hikari

  • Time: ~2 hr 15 min

  • Seats recommended but not mandatory

Kyoto evening:

  • Check-in

  • Light dinner

  • Early sleep

DAY 3 — Sat May 31

Kyoto: Temples & Gion

Morning:

  • Fushimi Inari Shrine (sunrise or early morning)

Midday:

  • Kiyomizu-dera Temple

  • Sannenzaka & Ninenzaka historic walking streets

Afternoon:

  • Philosopher’s Path

Evening:

  • Gion district (quiet lantern-lit streets)

DAY 4 — Sun June 1

Kyoto → Kiso Valley (Tsumago)

Transport:

  • Shinkansen Kyoto → Nagoya (~40 min)

  • Limited Express Shinano → Nagiso or Nakatsugawa (~1 hr 50 min)

  • Bus or taxi → Tsumago

Evening:

  • Check into Edo-era ryokan

  • Village walk

  • Kaiseki dinner

DAY 5 — Mon June 2

Tenkara Fishing → Drive to Matsumoto

Morning:

  • Guided tenkara fishing session in Kiso Valley

Midday:

  • Pick up rental car at Nagiso or Nakatsugawa

Afternoon:

  • Scenic drive into Matsumoto

  • Explore Nakamachi kura district

DAY 6 — Tue June 3

Matsumoto: Castle + Art

  • Matsumoto Castle

  • Matsumoto City Museum of Art (Yayoi Kusama)

  • Craft shops

  • Easy dinner

DAY 7 — Wed June 4

Printmaking Workshop → Drive to Nagano

Morning:

  • Hands-on moku-hanga (woodblock printmaking) workshop

Afternoon:

  • Drive to Nagano

  • Dinner and rest near Zenko-ji

DAY 8 — Thu June 5

Nagano + Togakushi Shrines (Car Day)

Plan:

  • Zenko-ji Temple

  • Nagano Prefectural Art Museum

  • Drive to Togakushi (cedar forest shrines)

  • Return to Nagano for dinner

  • Overnight Nagano

DAY 9 — Fri June 6

Nagano → Osaka → Okayama → Naoshima

Morning → Nagano to Osaka
Shinkansen travel (comfortable + scenic).
Easy transfer in Shin-Osaka.

Midday → Okayama Station
Quick lunch inside the station (udon, sushi, or bento).

Afternoon → Uno Port → Naoshima
Local JR train to Uno → ferry to Naoshima (15–20 min).
Arrive early afternoon.

Evening → Check-in + Coastal Art Walk
Explore:
• Kusama’s Red Pumpkin
• Benesse coastline sculptures
• Quiet beaches

Dinner: Benesse House Restaurant or Miyanoura cafés.
Stay on Naoshima.

DAY 10 — Sat June 7

Naoshima: Chichu + Art House Project

Morning — Chichu Art Museum
James Turrell
Claude Monet
Walter De Maria
Tadao Ando architecture
(Reserve timed tickets.)

Lunch
Terrace Restaurant at Chichu or Aisunao in Honmura.

Afternoon — Art House Project (Honmura)
• Minamidera (Turrell)
• Go’o Shrine
• Kadoya “Sea of Time”
• Haisha (Former Dentist House)

Evening
Benesse House Museum (optional)
Beach walk + dinner
Stay on Naoshima.

DAY 11 — Sun June 8

Naoshima → Teshima → Tokyo

Morning — Ferry to Teshima
Short scenic crossing.

Teshima Art Museum
A singular experience of space, water, sound, light.

Lunch — Shima Kitchen
Local, organic, community-based café.

Afternoon — Island Installations
Explore smaller artworks on foot.

Travel Back
Ferry Teshima → Uno
JR train Uno → Okayama
Shinkansen Okayama → Tokyo

Evening — Tokyo Check-In
Simple dinner + rest.

DAY 12 — Mon June 9

Tokyo: Slow + Beautiful Rest Day

Morning
Koishikawa Korakuen Garden or Hibiya Park
(peaceful, restorative)

Coffee + Light Exploring
Aoyama / Kagurazaka cafés and lanes

Lunch — Kagurazaka
Atmospheric neighborhood restaurants.

Afternoon
Easy shopping + wandering
Return to hotel for a rest break

Evening
Toufuya Ukai or Sushi Rangetsu
Gentle nighttime walk

DAY 13 — Tue June 10

Tokyo Art Day

Morning — Nezu Museum + Garden
Kengo Kuma architecture
Serene galleries + forest garden

Midday — Omotesando / Aoyama Walk
Prada Building
Omotesando Hills
Small design shops

Lunch — Aoyama Flower Market Tea House

Afternoon — Mori Art Museum
Contemporary art + Tokyo skyline view

Evening — Final Dinner
Sushi / tempura / kaiseki
Pack + relax

DAY 14 — Wed June 11

Fly Tokyo → Greenville

  • Train or limousine bus to NRT or HND

  • Fly home

  • Arrive in U.S. same day

SECTION 3 — PACKING LIST (CLEAN MODERN EDITION)

Clothing

  • Lightweight shirts

  • Quick-dry pants

  • Warm layer (fleece or sweater)

  • Rain jacket

  • Walking shoes

  • Sandals for ryokans/temples

  • Socks for temple visits

Artist Kit

  • Sketchbook

  • Fine pens + pencils

  • Travel watercolor or sumi ink kit

  • SD card backup

  • Roll-up pencil wrap

  • Battery pack

  • Folder for museum tickets

  • Zip pouch for paper scraps/textures

Fishing Gear

  • Quick-dry shorts

  • Water shoes

  • Small towel

  • Waterproof phone case

Electronics

  • USB-C multi-charger

  • Japan plug adapter

  • eSIM or pocket WiFi

  • Power bank

  • Headphones

Documents

  • Passport

  • International Driving Permit

  • Reservation printouts

  • Travel insurance

  • Itinerary

Miscellaneous

  • Daypack

  • Laundry sheets

  • Pocket umbrella

  • Coin purse

  • Water bottle

SECTION 4 — BOOKING TIMELINE

3–6 Months Before

□ Book flights (RT Tokyo)
□ Reserve Kyoto hotel
□ Book Kiso Valley ryokan
□ Reserve Koyasan temple lodging
□ Book tenkara guide
□ Moku-hanga printmaking workshop

1–2 Months Before

□ Reserve rental car (Nagiso → Kanazawa)
□ Set up JR train plans
□ Buy travel insurance

2 Weeks Before

□ Confirm all hotels
□ Activate eSIM
□ Print confirmations
□ Screenshot train times

1 Day Before Travel

□ Pack
□ Re-check passports
□ Hydrate
□ Print itinerary

SECTION 5 — TRANSPORT SUMMARY

International Flights

Greenville → Tokyo (May 29)
Tokyo → Greenville (June 11)

Japan Rail Segments

Tokyo → Kyoto → Nagoya → Kiso → Matsumoto → Nagano → Kanazawa → Osaka → Koyasan → Tokyo

Car Rental

Pickup: Day 5 – Nagiso/Nakatsugawa
Drop-off: Day 9 – Kanazawa Station