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Lagos to Tuscany's hill towns: Siena and San Gimignano

Lagos → Siena → San Gimignano

Siena
"PiazzadelCampoSiena.jpg" by Massimo Catarinella, CC BY-SA 3.0, via Wikimedia Commons· licence

Medieval towers & a shell-shaped square Best season (general guide): Apr–Jun, Sep–Oct

Tuscany's hill towns are best enjoyed slowly, after the day-trippers leave. This route spends four nights in Siena and two in San Gimignano, both listed by UNESCO. From Lagos you'll connect via a European hub to Florence, then take the bus south.

How to pace it: arrive in Siena and spend day two on the Piazza del Campo, the shell-shaped square sloping towards the town hall, one of Europe's great squares. Climb the Torre del Mangia, the town hall's bell tower and one of the tallest medieval towers in Italy, and inside the Palazzo Pubblico see Ambrogio Lorenzetti's frescoes of Good and Bad Government, painted in the 1330s. Day three is for the striped marble cathedral, with its inlaid floor and frescoed library, and its museum. Give day four to the Chianti countryside.

On day five, take the bus to San Gimignano, which once had around 72 towers built by rival families; 14 survive, and the tallest, the Torre Grossa, can be climbed. Day six is for the towers and the vineyards around the town, which make Vernaccia di San Gimignano, the first Italian wine to be given DOC status, in 1966.

Practical notes: spring and early autumn are the best seasons; summer is hot and busy. The Palio, a horse race between Siena's districts, fills the Campo on 2 July and 16 August, so book early or avoid those dates. Siena's traditional sweet is panforte, a dense cake of nuts and spices, and the city is home to Monte dei Paschi, founded in 1472 and often described as the oldest surviving bank in the world.

Safety: Canada asks travellers to Italy to take a high degree of caution (updated 29 Sep 2026), and the US rates Italy Level 2 (10 Sep 2026).

Suggested outline

  1. Lagos

    Start

  2. Siena

    By air · 4 nights suggested

    A Gothic city around a shell-shaped square.

  3. San Gimignano

    By bus · 2 nights suggested

    A hill town of medieval towers and white wine.

    San Gimignano towers skyline
    "San Gimignano skyline (6082044552).jpg" by Thomas Quine, CC BY 2.0, via Wikimedia Commons· licence

Day by day

  1. Day 1 · Siena — Arrive; bus from Florence· Lagos → Florence (by air), then Florence → Siena (overland)
  2. Day 2 · Siena — Piazza del Campo and the tower
  3. Day 3 · Siena — Cathedral and its museum
  4. Day 4 · Siena — Chianti countryside
  5. Day 5 · San Gimignano — Bus to San Gimignano· Siena → San Gimignano (by bus)
  6. Day 6 · San Gimignano — Towers and Vernaccia
  7. Day 7 · San Gimignano — Travel home from San Gimignano· San Gimignano → Florence (by bus), then Florence → Lagos (by air)

A suggested pace only; expedition days are set by the operator.

Flights, leg by leg

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Siena

Nearest airport: Florence Search fares · Florence ↗

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