Italy · Tuscany
Two nights each in Florence, Chianti and the Val d’Orcia, with Siena on the way and time for long lunches between vineyards.
Day 1 · Florence
Collect the car later: today is the Duomo, the Oltrarno and a bistecca dinner.
Day 2 · Florence
Two big museums with timed tickets, split by a long lunch at Mercato Centrale.
Day 3 · Greve in Chianti
Pick up the car outside the ZTL and drive the SR222 “Chiantigiana” through wine villages.
Getting there About 45 minutes from Florence; avoid driving into the ZTL zones.
Day 4 · Greve in Chianti
Loop through Radda, Castellina and a medieval abbey.
Day 5 · Siena
Park outside the walls, see Piazza del Campo and the striped cathedral, then continue to Pienza.
Getting there Greve to Siena 1 hour; Siena to Pienza 1 hour.
Day 6 · Pienza
Cypress roads, pecorino tastings and Brunello in Montalcino.
Day 7 · Florence
Morning in Pienza, then an easy motorway drive to return the car.
Getting there About 2 hours via the A1.
Keep planning
Japan
The classic first trip to Japan by train: four nights in Tokyo, a ryokan night in Hakone, then Kyoto’s temples and Osaka’s food.
Portugal · Lisbon
Three days of miradouros, pastéis de nata and tram rides, with a half-day in Sintra and a sunset in Belém.
Iceland
A full clockwise loop of Route 1 with realistic driving days: the south coast waterfalls, glacier lagoon, the East Fjords, Mývatn and Snæfellsnes.