✅ YES: Ship from Naoshima the morning after you arrive

Your timeline (clean + realistic)

Day 6 — Arrive Naoshima (midday)

• Check in

• Do art

• Do nothing with luggage yet

Day 7 — Morning (THIS is the key moment)

• After breakfast, before heading out:

  • Go to the front desk

  • Ask them to ship your main luggage to Tsumago

This timing is perfect.

🧳 WHAT HAPPENS NEXT (REALISTIC EXPECTATION)

• Luggage is picked up late morning / early afternoon

• It travels overnight

• It arrives in Tsumago either:

  • Late Day 8 (evening) or

  • Morning Day 9 (both are normal)

Ryokan staff will hold it and bring it to your room.

📍 WHAT YOU SAY (SIMPLE, NO STRESS)

At the Naoshima hotel front desk:

“We’d like to send this luggage to Matsushiroya Ryokan in Tsumago. We check in on June 4.”

They will:

• Fill out the form

• Confirm the delivery date

• Handle everything

You don’t need Japanese for this — they do it constantly.

🎒 WHAT YOU CARRY AFTER SHIPPING

Just a small overnight kit with:

• Clothes for Naoshima (Day 7)

• Clothes for Tsumago (Days 8–9)

• Toiletries

• Meds / essentials

That’s it.
No “extra outfits,” no bulk.

🚄 DAY 8 — THE PAYOFF

On Naoshima → Tsumago day:

• Ferry ✔

• Big stations ✔

• Rural bus ✔

• No suitcase

This is where you’ll feel very glad you shipped.

⚠️ ONE IMPORTANT DETAIL (DON’T SKIP THIS)

On the shipping form:

• Destination: Matsushiroya Ryokan

• City: Nagiso-machi, Kiso-gun, Nagano

• Check-in date: June 4

• Write your name clearly

The hotel will look up the address — you don’t need to.

💴 COST

• Roughly ¥2,000–¥3,000 per bag

• Paid at the hotel

• No tipping

🔑 BOTTOM LINE (THIS IS YOUR ANSWER)

✔ Yes, shipping the morning of your first full day on Naoshima works
✔ This avoids same-day rural delivery problems
✔ This eliminates the biggest luggage slog of the trip
✔ This is exactly how experienced travelers do it