Go There · Cortona, Tuscany, Italy — the rooftops

We were together. I forget the rest

In Cortona the stone houses climb toward the fortress, and at blue hour every window below you lights up, one kitchen at a time.

Our hour there

We had planned it badly. I wanted the fortress at blue hour, and you read the sign out loud: it closes before dark. So we came down past the mosaics with gold still on the stones and sat on the terrace of our room instead, a lantern between us, your book open on the same page for twenty minutes. The roofs went from orange to grey to something like ink. Swallows first, then a dog barking somewhere below, then one window, then a hundred. The wine tasted of a cool cellar. You laughed because I kept saying look, as if you weren't. We were together. I forget the rest.

You two can expect the light to go soft about twenty-five to forty minutes after sunset, which in mid-September means roughly a quarter to eight until a quarter past. It is still warm enough to sit out, and the town is quieter than in summer. Stone houses stack up the hill toward the Medici fortress, and the glow comes from ordinary windows, people cooking, people talking. Your own room light warms the wall behind you.

One honest thing: the rooms are non-smoking, so check the balcony rules before you light anything. And see the fortress at golden hour, not after; in September it closes at seven.

♡ We played first-lit-window, pointing across the roofs like spotters, and you won every round by claiming the one in our own room.

The frame, in real life

In the reel: A couple sits at a small café table on a vine-draped balcony, she reading and he smoking, above a hillside Tuscan village of stone houses, terracotta roofs and cypresses, its windows lit at blue hour.

The drawing matches no single viewpoint, so Cortona is our pick: stone houses climb its hill toward the Medici fortress, and hotel terraces look across the roofs, not just out over the valley. You can sit on a balcony very like this one, though the exact angle is the illustrator's. Montepulciano and San Gimignano could also fit, but we didn't research them.

When to go

September: warm enough for the balcony and quieter than summer. Late June also works, with a later blue hour.

The hour: Blue hour is about 19:45–20:15 in mid-September and about 21:20–21:35 in late June. These are our estimates from sunset times.

Avoid: Planning a blue-hour shot at the fortress, because it closes before dark. Lighting the cigarette indoors, since rooms are non-smoking; check the balcony rules first.

What it costs (EUR)

Shoestring: Ostello S. Marco private room about €45–55, beds from about €23. Fortress entry is €6.

Mid: Hotel San Michele superior room from about €90 a night (official rate unverified)

Splurge: Monastero di Cortona, about €240–600 a night. The Roofs room or suite likely sits at the top of that range (unverified).

Where to stay

4 stays, one of them is the view in the reel. The names and booking links are in the plan.

the reel stay

Via del Salvatore, Cortona

Book the Deluxe Cortona's Roofs Room or the Suite Cortona's Roofs, which has a private terrace suspended above the town.

name + booking links in the plan
AgodaBookingExpedia
mid

Via Guelfa 15, centro storico

A 15th-century palace whose upper-floor superior rooms look over the roofs or the valley.

name + booking links in the plan
mid

Opposite San Francesco church

A three-bedroom flat whose terrace has two armchairs and a small table, almost the café table in the reel.

name + booking links in the plan
shoestring

0.3 km from the centre

The simple private-room pick, a short walk from every viewpoint.

name + booking links in the plan

Exact shot locations

matches: the couple at the café table, vines, the lit village below

The roofs balcony

exact spot + hour + how-to in the plan

map
matches: the whole stack of roofs from above

Fortezza del Girifalco

exact spot + hour + how-to in the plan

map
matches: the soft valley beyond the village

Piazza Garibaldi belvedere

exact spot + hour + how-to in the plan

map
matches: the hillside of lit windows

Looking up from the Calcinaio

exact spot + hour + how-to in the plan

map

The plan

from the day-by-day plan · Up the hill
15:00Train to Camucia-Cortona or Terontola-Cortona, then a bus or taxi up to Piazza Garibaldi.
16:30Check in at Monastero di Cortona and ask for the roofs.
8 more timed stops across 3 days, in the plan

what's in the plan

  • 4stays with booking links, one of them is the view in the reel
  • 4exact shot spots with maps
  • 3days planned hour by hour: 10 timed stops
  • 4local spots with prices, a map pin each, a reserve link for every table
  • 3bookable moments (tickets, tours)
  • ✓eSIM / insurance / transfer links
  • ✓the hour to be there
  • ✓the trip desk: dated booking links, calendar, partner link, the concierge

Get the full plan

The stays with booking links, the exact spots with maps, the hour, the day-by-day plan, local spots, eSIM and insurance.

  • one payment, yours forever on this device + any device you sign in on
  • PDF + mobile page
  • updated when prices change
  • money back if a place is wrong (reply to the receipt)

Or comment SOMEWHERE on the reel and it lands in your DMs.

or
Prices and hours are a snapshot; confirm before booking. Some links in the full plan are affiliate links. Personal use only.