Tuscany & Umbria Vineyard Walks — Self-Launched

Arrive at Florence Santa Maria Novella and take the regional bus (Florence–Siena line, ~£9, 1h15) to Poggibonsi, then a local bus up to San Gimignano (~£2.50). Drop your bag at a guesthouse inside the walls or just below them, then walk the classic Via Francigena stage from Abbadia a Isola to Colle Val d'Elsa (~12km, 3-4hrs, waymarked white/red trail) — rolling vine-covered hills, stone farmhouses, cypress-lined lanes. Local buses link Colle Val d'Elsa back toward Poggibonsi or Siena. Reward yourself with a cone of San Gimignano's world-champion gelato and a sunset from the Rocca. Base night: San Gimignano (or Poggibonsi for cheaper beds).

🚌Florence–Poggibonsi regional bus ~£9; local buses ~£5 total

🛏Guesthouse or hostel in San Gimignano / Poggibonsi (~£45-55)

• →Via Francigena walk Abbadia a Isola–Colle Val d'Elsa (free, self-guided)
• →Wander San Gimignano's towers and piazzas (free)
• →Gelato + sunset at Rocca di Montestaffoli

Bus from San Gimignano/Poggibonsi to Monteriggioni (~£3) — a perfectly circular medieval walled village you can walk the ramparts of for a few euros. From here follow the Via Francigena south through olive groves and farmland to Siena (~20km, 5-6hrs; shorten it by bus to Castellina Scalo if you want a gentler day). Trains from Monteriggioni station back to Siena run hourly if you need a bail-out (~£3). Arrive Siena, check into a hostel or budget guesthouse inside the walls, and spend the evening in Piazza del Campo with a pizza slice and a cheap carafe of Chianti.

🚌Local buses ~£6; optional Monteriggioni–Siena train ~£3

🛏Hostel or budget guesthouse in Siena old town (~£40-50)

• →Monteriggioni wall walk (~£3)
• →Via Francigena Monteriggioni–Siena hike (free, self-guided)

Bus from Siena to Greve in Chianti (~£4, 1hr), then walk up to Montefioralle — a tiny stone hamlet curled around a castle. Join the waymarked Chianti Classico trail to Panzano (~8-10km, 3hrs) through vineyards and olive groves with long views across the Chianti hills. Book a farmhouse lunch and wine tasting direct with a Panzano winery or via GetYourGuide/Klook (~£45-60, the equivalent of the operator's Molino di Grace stop) — think pecorino, ribollita, roast pork and four Chianti Classico pours on a terrace. Bus back to Siena in the late afternoon. A DIY Pecorino tasting at a Greve cheese shop costs ~£8.

🚌Siena–Greve–Siena buses ~£8

🛏Hostel or budget guesthouse in Siena (~£40-50)

• →Chianti Classico trail Montefioralle–Panzano (free, self-guided)
• →Farmhouse lunch + Chianti wine tasting, booked direct (~£50)
• →Pecorino tasting in Greve (~£8)

Morning: book a small-group Siena walking tour on GetYourGuide or with a licensed local guide (~£25-30, 2hrs) covering Piazza del Campo, the Duomo and the contrade history — note that in Italy only city-licensed guides can legally give tours inside the old town, so book an official one rather than relying on a hostel guide. Lunch on pici cacio e pepe at a trattoria off the tourist track (~£12). Afternoon: bus to Radda in Chianti (~£4), local taxi or lift to Volpaia (~£10 shared) and walk the vineyard trail down to Lamole (~7km), then back via Greve. Evening: a self-arranged wine-pairing dinner at an Enoteca or agriturismo (~£35) replaces the group's included pairing dinner.

🚌Local buses Siena–Radda–Greve ~£8; shared taxi ~£10

🛏Hostel or budget guesthouse in Siena (~£40-50)

• →Siena small-group walking tour via GetYourGuide (~£27)
• →Volpaia–Lamole vineyard walk (free)
• →Wine-pairing dinner at an enoteca (~£35)

Train Siena–Chiusi-Chianciano Terme (~£6), then local bus to Montepulciano (~£3). Wander the steep medieval lanes and taste Vino Nobile at an enoteca (~£10-15 for a flight). Bus on to Pienza (~£3) and follow the Pienza loop trail via the Romanesque church of Corsignano onto the Strada dei Gladiatori — the exact cypress-dotted ridge Ridley Scott filmed for Gladiator (~6km, 2hrs, free). In the late afternoon bus/train to Chiusi and on to Città della Pieve (~£8) in Umbria, checking into a family-run guesthouse or budget hotel in the old town for two nights.

🚌Siena–Chiusi train ~£6; local buses ~£9; Chiusi–Città della Pieve bus/train ~£5

🛏Guesthouse in Città della Pieve old town (~£40-45)

• →Montepulciano walking wander + Vino Nobile tasting (~£12)
• →Pienza & Gladiator trail loop hike (free)
• →Città della Pieve evening passeggiata (free)

Morning cooking class with a local Umbrian cook — book direct with an agriturismo or via GetYourGuide/Klook (~£55-70 for a half-day class including lunch with wine), making tagliatelle al ragù, umbrian lentil dishes and tiramisù. Afternoon free: explore Città della Pieve's brick lanes, the Oratory of Santa Maria dei Bianchi and the viewpoint over the Chiana valley, or take the local bus to Lake Trasimeno (~£4) for a swim and a lakeside aperitivo. Evening: cheap trattoria dinner in town (~£15).

🚌Local buses / on foot ~£5

🛏Guesthouse in Città della Pieve old town (~£40-45)

• →Umbrian cooking class with lunch (~£60)
• →Città della Pieve old town and viewpoints (free)
• →Optional Lake Trasimeno trip (~£4 bus + £3 ferry)

Train Città della Pieve/Chiusi to Rome Termini (~£12-15, 1h45). Check into a hostel near Termini or Monti (~£35-45 dorm, ~£65 private). Afternoon: pick your Rome 'OMG Day' — a small-group guided walking tour of the Centro Storico on GetYourGuide (~£25), or an hour-long Vespa sidecar/scooter tour (~£60-75). Add a Colosseum or Vatican ticket booked online in advance (~£18-30). Dinner in Trastevere: supplì, carbonara and a carafe of house wine (~£18).

🚌Regional train to Rome ~£14; Rome metro/bus day ticket ~£6

🛏Hostel or budget hotel in Rome (~£40-60)

• →Rome walking tour or guided Vespa tour via GetYourGuide (~£25-70)
• →Optional Colosseum/Vatican entry (~£20)
• →Trastevere evening wander (free)

A last espresso and cornetto at a neighbourhood bar (~£3), then one more free stop — the Pantheon, Piazza Navona or a climb of the Campidoglio — before heading to Fiumicino by the Leonardo Express train (~£12) or Terravision bus (~£6) for your flight home.

🚌Leonardo Express ~£12 or airport bus ~£6

🛏—

• →Free morning sightseeing in central Rome