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Florence · Siena · Val d'Orcia7 daysPremiumDemo itinerary

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

T2 tram from Florence Airport to the centre

8/10Transport · 12:00 · 25 min

Florence

💬 The tram stops right outside arrivals; validate the ticket on board.

Cost: €2.00Booking request →

Hotel Brunelleschi

9/10Hotel · 14:00 · 60 min

Florence

💬 Built into a medieval tower two minutes from the Duomo; quiet at night despite the location.

Cost: €250.00 – €420.00

Piazzale Michelangelo at sunset

9/10Attraction · 18:30 · 90 min

Florence

💬 Walk up from San Niccolò through the rose garden rather than taking the bus.

Cost: €0.00Booking request →

Dinner in the Oltrarno

9/10Restaurant · 20:30 · 120 min

Florence

💬 Bistecca alla fiorentina is sold by weight — usually about a kilo for two, served rare.

Cost: €40.00 – €70.00Booking request →

Day 2 · Duomo, Uffizi and Ponte Vecchio

Duomo complex and Brunelleschi's dome climb

10/10Tour · 08:15 · 150 min

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.

Cost: €30.00 – €35.00

Uffizi Gallery

10/10Attraction · 12:30 · 180 min

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.

Cost: €25.00 – €30.00

Ponte Vecchio at dusk

8/10Attraction · 18:30 · 45 min

Florence

💬 Best seen from the next bridge downstream, Ponte Santa Trinita.

Cost: €0.00Booking request →

Day 3 · David, the market and Boboli

Galleria dell'Accademia — Michelangelo's David

9/10Attraction · 08:30 · 90 min

Florence

💬 Take the first slot of the day; you'll have David almost to yourself for ten minutes.

Cost: €16.00 – €20.00

Lunch at Mercato Centrale

8/10Restaurant · 11:00 · 90 min

Florence

💬 Downstairs is the traditional market (try a lampredotto sandwich); upstairs is the food hall.

Cost: €15.00 – €25.00Booking request →

Pitti Palace and Boboli Gardens

8/10Attraction · 14:00 · 180 min

Florence

💬 Boboli is steep in places — go up to the Kaffeehaus terrace for the view.

Cost: €16.00 – €25.00

Aperitivo in Piazza Santo Spirito

8/10Restaurant · 19:00 · 90 min

Florence

💬 A spritz and snacks on the steps with the locals.

Cost: €15.00 – €30.00Booking request →

Day 4 · Drive to Siena

Pick up a rental car at Florence Airport

8/10Car rental · 09:00 · 45 min

Siena

💬 Never drive into Florence's ZTL (limited-traffic zone) — cameras fine you automatically.

Cost: €200.00 – €350.00

Piazza del Campo

10/10Attraction · 12:30 · 60 min

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.

Cost: €0.00Booking request →

Siena Cathedral

10/10Attraction · 14:00 · 120 min

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.

Cost: €15.00 – €20.00

Hotel inside Siena's walls

8/10Hotel · 17:00 · 60 min

Siena

💬 Park outside the walls and use the public escalators or lifts up into the centre.

Cost: €140.00 – €220.00

Day 5 · Pienza and the Vitaleta chapel

Pienza

10/10Attraction · 10:30 · 150 min

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.

Cost: €0.00 – €20.00Booking request →

Agriturismo in the Val d'Orcia

9/10Hotel · 14:00 · 60 min

Val d'Orcia

💬 Pick one between Pienza and San Quirico; many serve dinner from their own farm.

Cost: €160.00 – €260.00

Cappella della Madonna di Vitaleta

9/10Attraction · 17:30 · 60 min

Val d'Orcia

💬 Walk in on the gravel track from the road near San Quirico; golden light before sunset.

Cost: €0.00Booking request →

Dinner in San Quirico d'Orcia

8/10Restaurant · 20:00 · 90 min

Val d'Orcia

💬 Pici pasta with ragù or cacio e pepe.

Cost: €30.00 – €50.00Booking request →

Day 6 · Montalcino, Bagno Vignoni and Montepulciano

Brunello tasting in Montalcino

9/10Tour · 10:00 · 180 min

Val d'Orcia

💬 Book a winery visit and choose a designated driver — the roads are winding.

Cost: €30.00 – €60.00

Bagno Vignoni

8/10Attraction · 15:00 · 60 min

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.

Cost: €0.00Booking request →

Montepulciano

9/10Attraction · 17:00 · 150 min

Val d'Orcia

💬 Steep walk up the Corso; several historic cellars under the main street offer Vino Nobile tastings.

Cost: €0.00 – €30.00Booking request →

Day 7 · Sant'Antimo and back to Florence

Abbey of Sant'Antimo

9/10Attraction · 09:30 · 60 min

Florence

12th-century Romanesque abbey church near Castelnuovo dell'Abate, south of Montalcino.

💬 Romanesque abbey among olive trees; quiet and beautiful in the morning.

Cost: €0.00Booking request →

Drive back and return the car at Florence Airport

7/10Transport · 12:00 · 150 min

Florence

💬 About two hours via the Siena–Florence highway; allow time to refuel.

Cost: €0.00Booking request →

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