Tuscany
road trip

Land at Florence Peretola or Pisa. Drop bags at the Airbnb in Oltrarno (cheaper, quieter side of the river) or Santa Croce (more central). DO NOT rent the car yet — you don't need it until Day 3.

Walk along the Arno, cross the Ponte Vecchio at golden hour, climb up to Piazzale Michelangelo for the postcard view. Stop at Gelateria della Passera on the way.

Aperitivo at Le Volpi e l'Uva (tiny wine bar in Oltrarno, friendly to non-Italians). Dinner at Trattoria Cammillo or Il Santo Bevitore. Limoncello, then home — tomorrow is big.

Pre-booked Uffizi entry at 8:30am (essential — walk-up is 2-3 hours of queue). 2-3 hours is enough. Coffee and pastry at Caffè Gilli.

Climb the Duomo dome (book the combo ticket with the baptistery). Late lunch at All'Antico Vinaio (panini institution — split four panini between six and you've eaten well).

Bistecca alla Fiorentina at Trattoria Mario (lunch only, go on day 3) — OR — Trattoria Sostanza for a smaller-group steak. Walk it off along the Arno, gelato, in bed by midnight.

Quick Florence morning — Mercato Centrale for breakfast and food shopping. Pick up the rental car at 10am from a downtown location (NOT the airport — saves a transfer).

Drive south through Chianti. Stop at Castello di Verrazzano for a winery lunch + tasting (book in advance). Optional second stop at Greve in Chianti for the main square.

Arrive Siena late afternoon. Check into the agriturismo or Airbnb. Walk into the Piazza del Campo at sunset — one of the great Italian piazzas. Dinner at La Taverna di San Giuseppe or Osteria Le Logge.

Slow Siena morning. Climb the Torre del Mangia (free if you're under 70kg lol — kidding, 10 EUR, worth it). Visit the cathedral.

45-min drive to San Gimignano. The 'medieval Manhattan' — 14 surviving towers. Touristy but unmissable. Climb the Torre Grossa, gelato at Dondoli (multiple world-champion gelatiers).

Drive back to Siena. Aperitivo on Piazza del Campo (overpriced but the view is the view). Cheaper dinner at Trattoria Papei or pizza at Pizzeria Le Logge.

Drive 1h south into the Val d'Orcia — UNESCO landscape, cypress-lined roads, the photo you've seen 100 times. Stop at the famous 'Gladiator road' near San Quirico for the group photo.

Pienza for lunch — try the pecorino at any cheese shop, the town smells like it. Then Montepulciano in the afternoon for Vino Nobile tastings at Avignonesi or De' Ricci.

Optional: drive to Bagno Vignoni for a soak in the open-air thermal baths at sunset. Dinner back at your agriturismo (most have an in-house restaurant — book the night before).

Drive to Montalcino. Brunello tasting day. Book ONE serious winery (Casanova di Neri, Argiano, Il Poggione) and ONE casual stop. Don't try to do four — the roads are winding and the wines are 14%+.

Long lunch at the winery or at Re di Macchia in Montalcino town. Designate a driver! Or split costs of a private driver-guide for the day (~250 EUR, well worth it for a group of 6).

Drive 2h back toward Florence. Stop in Lucca for dinner — the perfect Tuscan small town. Walk the city walls at dusk. Sleep in Lucca or push the last 30 minutes to a hotel near Pisa airport for tomorrow.

Pisa for the Leaning Tower — yes you do the photo, no judgment. 90 minutes is enough. Coffee on Piazza dei Cavalieri.

Return the rental car at Pisa airport (avoids Florence city return fees). Late lunch at the airport or in Pisa centre. Flights typically afternoon/evening.

Fly home. The group chat will be 80% photos of food and 20% 'when's the next one' for the next two months.