Love it? Take it with you
A free personal copy · fresh dates · everything editable
There are two kinds of Tuscany trips: the kind that sees it through a bus window, and the kind that pulls over because a field demanded it. This itinerary — built by Max from a real request, a couple asking for "vineyards, art and food, no rush" — is the second kind.
The logic is simple: start with the countryside. Three nights on a working cheese farm facing Pienza, with wine days in Montepulciano and Montalcino and an evening at Bagno Vignoni's thermal square. Only then, via Siena, comes Florence — four nights of the Uffizi, Brunelleschi's dome, trattorias and the artisan quarter. Next to every choice, Max's "why".
Read it as inspiration — or hit "Copy this trip": you'll get your own version with upcoming dates, car included, and change whatever you like. Prices are honest estimates as of writing; your copy re-checks them.
LY 385Max's pickOutbound: Thursday · 06:15–09:40 · TLV→FCO · Direct
Return: Thursday · 17:50–22:05 · FCO→TLV · Direct
₪1,980 per person
Why it's here: Landing in Rome at 9:40 — you pick up the car, and by two you're holding a glass of wine above the Val d'Orcia.
AZ 809CheapestOutbound: Thursday · 12:30–15:50 · TLV→FCO · Direct
Return: Thursday · 08:45–13:05 · FCO→TLV · Direct
₪1,750 per person
Why it's here: About $65 less per person — but you reach the farm only toward evening. Worth it if day one matters less to you.
Prices and times on this page are honest estimates, for illustration. When you copy the trip, your version opens with upcoming dates and prices are re-checked.
Val d'Orcia · 3 nights
Pienza hills · ★★★ · 9.4 640 reviews
₪980 per night
₪2,940 for 3 nights
Double room with valley view · Breakfast included · Pay at the property
Why it's here: A real farm on a hill facing Pienza — pecorino made on site in the morning, a sunset no camera gets right in the evening. This is the heart of Tuscan romance.
Florence · 4 nights
Historic center, 3 min from Ponte Vecchio · ★★★★ · 8.9 1,300 reviews
₪1,150 per night
₪4,600 for 4 nights
Deluxe double room · Room only · Pay at the hotel
Why it's here: A boutique in the very center — the Duomo, the Uffizi and the bridge are all a short walk, and its rooftop looks over every roof in Florence.
Fiat 500X
₪1,680
Pickup: Rome Fiumicino Airport · Thu 10:30
Drop-off: Rome Fiumicino Airport · Thu 14:30
Unlimited km · Full to full · Free cancellation until 48 hours before pickup
The exact calendar your copied trip opens with — flights, hotel, and every place in its part of the day. Tap any block to see it on the map.
You land in Rome and within a couple of hours trade motorways for hills. First evening: a farm dinner and a sky full of stars.
About two and a quarter hours of road that gets prettier by the kilometer — until the hills begin.
Why it's here: You start with the countryside, not the city — the head resets on day one, and Florence waits for the finale.
Drop the bags, taste cheese straight from the dairy, claim a chair facing the valley.
Why it's here: You asked for romantic, not packed — day one ends with no plans on purpose.
One long table, homemade pasta, this morning's cheeses and the neighbors' wine — everything from meters away.
Why it's here: The first dinner sets the tone — which is exactly why I chose a farm that cooks, not just sleeps.
The day you came for: a Renaissance town, an Etruscan wine cellar, and a square made entirely of hot water.
A tiny Renaissance town whose lanes are named "Kiss Street" and "Love Street", with a balcony over the whole valley.
Why it's here: Closest to the farm and the most romantic — you start on the right foot. Try aged pecorino with honey.
Vino Nobile tasting in Etruscan cellars beneath the town — giant barrels and two-thousand-year-old stone.
Why it's here: You marked wine and food — this is the full story: a tasting inside a cellar that's an attraction in itself.
A village whose main square is a 16th-century thermal pool, steaming into the evening.
Why it's here: At sunset, when the steam rises off the water — the most romantic moment in the valley. Free.
Brunello in the morning, cypresses in the afternoon — the most photographed day of the trip.
A family winery facing Montalcino's walls — a walk in the vineyard, then three glasses that explain Brunello.
Why it's here: If you taste one wine in Tuscany — make it Brunello where it was born. I booked the morning, before the crowds.
The most photographed curves in Italy — stop, climb to the viewpoint, take your time.
Why it's here: For the photo that hangs in your living room a decade from now. Late-afternoon light is the secret.
Pici with wild-boar ragù, a glass of Nobile, one dessert, two spoons.
Why it's here: You close the countryside chapter where it opened — close, delicious, no night driving.
You leave the valley through Siena, and trade rural quiet for the gold of Ponte Vecchio.
The shell-shaped square, the striped cathedral, and an espresso standing up like a local.
Why it's here: Siena sits exactly on the way north — two hours here are the difference between crossing Tuscany and meeting it.
About an hour and a half, trading countryside for city. A proper garage near the hotel.
Why it's here: You arrive mid-afternoon — exactly enough day left for a first evening on the bridge.
The old bridge at the hour the goldsmiths close and the light turns gold — then a spritz on the Arno.
Why it's here: The moment Florence explains itself — no tickets, no line. Just arrive fifteen minutes before sunset.
The big Renaissance day: Botticelli in the morning, 463 steps in the afternoon, and 1869's butter chicken at night.
Botticelli, Leonardo, Caravaggio — the collection that invented what we call Western art.
Why it's here: You marked art — I took the 8:15 entry, ahead of the groups. Two or three hours is the right peak, not a whole day.
Italy's most famous schiacciata — the line moves fast, the panino is huge, you share one on the curb.
Why it's here: After a museum morning comes a street lunch — as Florentine as it gets, under €15 for two.
463 steps inside the double dome — at the top, all of Florence under your feet.
Why it's here: Must be booked with a time slot — I took late afternoon, when the light on the rooftops is best and the line shortest.
A trattoria from 1869 with two shared tables, bistecca fiorentina and a butter chicken famous worldwide.
Why it's here: No more local dinner exists in Florence. Call a week ahead, arrive hungry, order the chicken.
A breathing day: circle an entire city by bike, on top of its wall.
Rent a pair of bikes and circle the whole city on a broad, tree-lined 16th-century wall — 4 km of calm.
Why it's here: A breathing day between city days — an hour's drive, zero lines, and the coffee in Piazza dell'Anfiteatro is worth the trip.
A tiny wine bar behind Ponte Vecchio — small-producer bottles and crostini that aren't on menus.
Why it's here: After a day on wheels — a glass of local red where Florentines keep it for themselves.
No museums today — a market, the artisans, and one last sunset above it all.
The great iron market: prosciutto, truffles, lampredotto for the brave — and good coffee between stalls.
Why it's here: A last morning without a schedule — eat what you see, buy olive oil for home.
Leather workshops, gilders and marbled-paper shops — the quiet side of the river, shopping with a soul.
Why it's here: Your souvenir from Florence isn't bought by the Duomo — it's bought here, from the artisan who made it.
The classic terrace over the whole city, then down to San Niccolò for one last proper Italian dinner.
Why it's here: You close the trip from above — with all of Florence in the last light. A cliché? Completely. Worth every second.
You return the car with the smell of cypress still in it.
About three easy hours — leave after a slow morning, fill the tank before drop-off.
Why it's here: I left a generous margin before the flight — a calm end to a calm trip.
The hotel and every place on the itinerary — tap 📍 next to a place to focus it here
Prices and times on this page are honest estimates, for illustration. When you copy the trip, your version opens with upcoming dates and prices are re-checked.
This itinerary comes to about ₪14,500 (≈ $4,200) for two: roughly ₪4,000 for direct flights to Rome, ₪7,500 for seven nights (agriturismo + a Florence boutique), ₪1,700 for a week's rental car, and ₪1,300 for tastings and tickets. A simpler farm stay brings it down; private wineries take it up.
Eight days is the comfortable formula: three nights in the countryside (Val d'Orcia) and four in Florence, with Siena on the way. Any less and you're choosing between the vineyards and the Renaissance — and that combination is exactly what makes Tuscany.
In the countryside — absolutely: there's no other way to reach the agriturismo, the wineries and the cypress roads. In Florence itself a car is useless (and expensive to park) — which is why the route concentrates the driving in the rural half and keeps the city entirely on foot.
Late September to early October is the golden window: harvest season, 23–24°C, soft light and fewer tourists than summer. May–June is lovely too — just greener and slightly busier.
Three things: a timed Uffizi entry, the Brunelleschi dome climb (sold by time slot), and a table at Trattoria Sostanza. Wine tastings are nice to book ahead but usually work out even two days before.
One click creates your own copy of this itinerary — upcoming dates, re-checked prices, and the freedom to change every detail. Or have Max build you a new one, from scratch, just for you.