Tuscany in 7 days — Florence, Siena and the cypress roads of Val d'Orcia
by Dan Cohen · Updated Nov 1, 2026
Three nights in Florence for the Duomo climb, the Uffizi and David, then a rental car to Siena and two slow days in Val d'Orcia: Pienza, the Vitaleta chapel, Brunello in Montalcino, the thermal square of Bagno Vignoni and Montepulciano. Museum slots, car and hotels booked through TripShare partners.
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Day 1 · Arrival in Florence
Florence
💬 The tram stops right outside arrivals; validate the ticket on board.
Florence
💬 Built into a medieval tower two minutes from the Duomo; quiet at night despite the location.
Florence
💬 Walk up from San Niccolò through the rose garden rather than taking the bus.
Florence
💬 Bistecca alla fiorentina is sold by weight — usually about a kilo for two, served rare.
Day 2 · Duomo, Uffizi and Ponte Vecchio
Florence
Florence Cathedral with Brunelleschi's 15th-century dome, Giotto's bell tower and the Baptistery.
💬 The Brunelleschi Pass gives the dome climb a fixed time slot; book two to three weeks ahead.
Florence
One of the world's great Renaissance collections, in the Medici offices by the Arno.
💬 Timed entry; do the Botticelli rooms first, then coffee on the terrace above the Loggia dei Lanzi.
Florence
💬 Best seen from the next bridge downstream, Ponte Santa Trinita.
Day 3 · David, the market and Boboli
Florence
💬 Take the first slot of the day; you'll have David almost to yourself for ten minutes.
Florence
💬 Downstairs is the traditional market (try a lampredotto sandwich); upstairs is the food hall.
Florence
💬 Boboli is steep in places — go up to the Kaffeehaus terrace for the view.
Day 4 · Drive to Siena
Siena
💬 Never drive into Florence's ZTL (limited-traffic zone) — cameras fine you automatically.
Siena
Shell-shaped medieval square where the Palio horse race is run each July and August.
💬 Sit on the sloping brick like everyone else; coffees on the rim cost double.
Siena
Romanesque-Gothic cathedral with a striped marble interior, the Piccolomini Library and an inlaid marble floor.
💬 The OPA SI pass covers the cathedral, crypt, baptistery and museum; the inlaid marble floor is fully uncovered only part of the year.
Siena
💬 Park outside the walls and use the public escalators or lifts up into the centre.
Day 5 · Pienza and the Vitaleta chapel
Val d'Orcia
Small Renaissance 'ideal town' rebuilt by Pope Pius II, overlooking the Val d'Orcia.
💬 Walk the panoramic wall and the little lanes like Via dell'Amore; buy aged pecorino di Pienza.
Val d'Orcia
💬 Pick one between Pienza and San Quirico; many serve dinner from their own farm.
Val d'Orcia
💬 Walk in on the gravel track from the road near San Quirico; golden light before sunset.
Day 6 · Montalcino, Bagno Vignoni and Montepulciano
Val d'Orcia
💬 Book a winery visit and choose a designated driver — the roads are winding.
Val d'Orcia
Village whose main square is a Renaissance-era pool of thermal water.
💬 The pool in the square is for looking only; the free hot streams below the village are where people dip their feet.
Val d'Orcia
💬 Steep walk up the Corso; several historic cellars under the main street offer Vino Nobile tastings.
Day 7 · Sant'Antimo and back to Florence
Florence
12th-century Romanesque abbey church near Castelnuovo dell'Abate, south of Montalcino.
💬 Romanesque abbey among olive trees; quiet and beautiful in the morning.
Florence
💬 About two hours via the Siena–Florence highway; allow time to refuel.
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