Tuscany Walking & Wine — Self-Launched

Fly into Pisa Galileo Galilei (PSA) and take the PisaMover shuttle into Pisa Centrale (~£5, 5 mins) — far cheaper than a taxi. Check into a central guesthouse or budget hotel a short walk from the river. Explore! starts with an evening airport transfer; instead use the afternoon to wander Piazza dei Miracoli and climb the Leaning Tower if you've pre-booked a slot online (€20, ~£17 — book a week ahead as slots sell out). Evening aperitivo on Borgo Stretto, then an early night ahead of tomorrow's hike. Grab a supermarket picnic for the trail.

🚌PisaMover shuttle airport → Pisa Centrale ~£5

🛏Central Pisa guesthouse or budget hotel (double/twin ~£55–70/night, or hostel dorm ~£25–35)

• →Piazza dei Miracoli & Duomo exterior (free)
• →Climb the Leaning Tower of Pisa (pre-book, ~£17)
• →Evening stroll along the Arno

Take the regional train from Pisa Centrale to Pontedera or Empoli (~£4, 30–45 mins), then a local bus toward San Gimignano, or simply walk the best section of the Via Francigena pilgrim route into San Gimignano through vineyards and cypress ridges (~12–14 km, 4–5 hrs). Explore! includes a guided hike; solo, use the free Via Francigena GPX/app and waymarking — the route is well signed. Afternoon: pre-book a small-group tasting at a San Gimignano estate such as Sovestro (~£25–35 incl. Vernaccia and Chianti Colli Senesi samples). Climb Torre Grossa (~£8) and see the Duomo frescoes if time allows. Late afternoon bus San Gimignano → Poggibonsi → Castellina in Chianti (~£4–5) and check into a Chianti agriturismo or guesthouse.

🚌Train Pisa → Empoli/Pontedera ~£4; local bus to San Gimignano ~£3; buses via Poggibonsi to Castellina ~£5

🛏Chianti agriturismo or rural guesthouse near Castellina in Chianti (~£50–70/night double)

• →Self-navigated Via Francigena walk (~13 km)
• →Sovestro winery tasting, San Gimignano (~£30, book direct or via GetYourGuide)
• →Torre Grossa & Duomo, San Gimignano (~£10)

A full walking day on the white gravel roads of Chianti Classico — plan a 14–18 km loop from Castellina through olive groves and vineyards, or the marked Chianti Classico trails that pass Monteriggioni-style ridge views. Book a light-lunch and wine-tasting slot directly with Castello La Leccia (~£40–50 for tasting plus cheese and salumi board) — email or use their website, as small groups fill quickly. Afternoon back in Castellina: poke around the village, the Etruscan tumulus of Montecalvario, and a Chianti Classico enoteca. If your guesthouse has a pool, the itinerary's own advice stands — use it.

🚌On foot; occasional local bus if you cut the loop short ~£3

🛏Chianti agriturismo near Castellina in Chianti (~£50–70/night double)

• →Strade bianche hiking loop (~15 km)
• →Castello La Leccia wine tasting + light lunch (~£45, book direct)
• →Castellina village and Montecalvario tomb (free)

Bus from Castellina to Siena (~£4, 45 mins) and spend the morning walking the shell-shaped Piazza del Campo, climbing Torre del Mangia (~£10, book a timed slot) and seeing the Duomo's inlaid marble floor (~£6). Skip the paid orientation tour — download a free self-guided audio walk or use the numbered city route and just wander the contrade alleys. Early afternoon: bus Siena → Buonconvento or San Quirico d'Orcia, then connect to Pienza (~£6–8 total, 1.5–2 hrs). Check into a small hotel inside Pienza's walls and eat pecorino and pici for dinner.

🚌Bus Castellina → Siena ~£4; bus Siena → Pienza (via Buonconvento/San Quirico) ~£7

🛏Small 3* hotel or guesthouse inside Pienza's historic centre (~£65–85/night double)

• →Piazza del Campo & Siena contrade walk (free)
• →Torre del Mangia climb (~£10)
• →Duomo di Siena (~£6)

Walk the classic panoramic loop south of Pienza past the Cappella della Vitaleta — the cypress-lined chapel that opens Ridley Scott's Gladiator — on a signed 10–12 km circuit through the clay hills of the Val d'Orcia (3–4 hrs, easy-moderate). Take a picnic from Pienza's Friday market or the alimentari on Corso il Rossellino. Back in town, do the cheese tasting at the Armellini family shop (~£8–12) and sample pecorino di Pienza stagionato in walnut leaves. Sunset from the Belvedere terrace over the valley.

🚌On foot from Pienza's centre

🛏Small 3* hotel or guesthouse inside Pienza (~£65–85/night double)

• →Vitaleta / 'Gladiator' panoramic loop hike (~11 km)
• →Pecorino tasting at Armellini (~£10)
• →Pienza belvedere sunset (free)

Morning bus Pienza → Montalcino (~£4, 50 mins via Torrenieri or direct depending on season). Book a Brunello di Montalcino tasting directly with a small cantina in the town or along the Strada del Brunello (~£25–40 for 3–4 pours). Then walk or take a short local bus down to the Val d'Orcia and hike the ridge trail San Quirico d'Orcia → Pienza (~12 km, 3 hrs) with a picnic lunch of pecorino, finocchiona and focaccia. Finish in Pienza for a long dinner.

🚌Bus Pienza → Montalcino ~£4; local bus or on foot to trailhead ~£3; return bus San Quirico → Pienza ~£3

🛏Small 3* hotel or guesthouse inside Pienza (~£65–85/night double)

• →Brunello di Montalcino cellar tasting (~£30, book direct)
• →Val d'Orcia ridge hike San Quirico → Pienza (~12 km)
• →Picnic lunch along the trail (~£8)

Bus Pienza → Buonconvento or Siena, then regional train Siena → Firenze Santa Maria Novella (~£9 all-in, 2.5–3 hrs total). Check into a budget hotel or guesthouse just outside the ZTL (the traffic-restricted centre) to keep costs down. Afternoon: a free self-guided route — Duomo exterior and Brunelleschi's dome (book the dome climb ~£25 if you want it), Piazza della Signoria, Ponte Vecchio at sunset, and the uphill walk to Piazzale Michelangelo for the classic skyline view. Optional: a GetYourGuide Uffizi skip-the-line entry (~£25).

🚌Bus Pienza → Siena ~£5; regional train Siena → Florence ~£9

🛏Budget hotel or guesthouse in Florence, Oltrarno or near Santa Maria Novella (~£70–95/night double)

• →Self-guided Duomo & Piazza della Signoria walk (free)
• →Ponte Vecchio & Piazzale Michelangelo (free)
• →Optional Uffizi entry (~£25) or dome climb (~£25)

Morning at the Mercato Centrale food hall for a late breakfast, a last espresso, and a final wander through San Lorenzo and Santa Croce. Tram T2 from Alamanni/Unità to Florence Peretola airport (~£1.70, 20 mins) or train to Pisa for cheaper flights (~£9). If you're staying on, Florence is the perfect rail hub for Bologna, Lucca or Rome.

🚌Tram T2 to Florence airport ~£2, or train to Pisa ~£9

🛏—

• →Mercato Centrale breakfast (free entry)
• →Santa Croce square and San Lorenzo market (free)