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Tuscany: Florence & the Hill Towns – Route Guide

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A cypress-lined lane through the rolling hills of the Val d'Orcia
Photo: Iaia quark · CC0 · Wikimedia Commons

Set out from Florence for Lucca's walls, Pisa's riverside and the hill towns of San Gimignano, Siena and Montepulciano before returning to Florence. Seven days give each town room to breathe, with different walks in Florence at the start and finish. Tower climbs, ticketed monuments, wine visits and guided outings are yours to add separately.

Tuscany: Florence & the Hill Towns is a 380 km loop (self-drive). It works best as a 7-day trip; the plan below is the 7-day version for October, built from 332 verified places, with planned transit times, opening hours and daylight checked.

7
days
380km
distance
6
Stops
332
curated stops

View ready-made plans 7-day plan · best time to go

The route

Florence→ 80 kmLucca→ 20 kmPisa→ 80 kmSan Gimignano→ 40 kmSiena→ 70 kmMontepulciano
San Gimignano’s stone towers and rooftops above the Tuscan countryside

San Gimignano · Day 5

San Gimignano public walled-centre circuit

Use municipal parking outside the video-controlled ZTL and walk a bounded public circuit through the walled centre and exterior viewpoints. Tower climbs, paid interiors, tastings, events and guided products remain optional.

7-day plan →

Photo: Giorgio Galeotti · CC BY 4.0

What you'll see

Florence public north-centre circuit
Park outside Florence’s ZTL and follow a bounded public circuit through the cathedral district, Piazza della Signoria and surrounding public streets. Paid monuments and museums, events and guided products remain optional.
Florence
Lucca public walls-and-centre circuit
Park outside Lucca’s ZTL for a bounded public circuit along accessible wall sections and through the historic centre. Tower climbs, paid interiors, cycling hire, events and guided products remain optional.
Lucca
Pisa public centre-and-Arno circuit
Use lawful parking outside restricted streets for a bounded public circuit linking Pisa’s centre, Arno and exterior landmark views. Tower and monument entry, events and guided products remain optional.
Pisa
Siena public historic-centre circuit
Use official parking beside Siena’s ZTL for a bounded public circuit through Piazza del Campo and surrounding contrade streets. Tower and museum entry, Palio dates, events and guided products remain optional.
Siena
Montepulciano public ridge-town circuit
Park outside Montepulciano’s seasonal ZTL and walk a bounded public ridge-town circuit through public streets and viewpoints. Cellars, tastings, paid interiors, events and guided products remain optional.
Montepulciano
Florence public Oltrarno-and-Arno circuit
Use lawful outer parking and public streets for a separate bounded Arno-and-Oltrarno circuit. Palace and garden entry, hill transport, events and guided products remain optional.
Florence

Choose your length

7-day plan13 stops · 11.8 h transit1.9 stops/day · 1.7 h transit/daySee the full plan →

When to go

Best months: September, October

Milder conditions and useful daylight generally suit the public circuits. Check current roads, parking, weather, traffic and local access.

See the month-by-month breakdown →

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View ready-made plans