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Tuscany Road Trip: Florence, Chianti and Val d'Orcia
Routes › Europe › Italy
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Tuscany Road Trip: Florence, Chianti and Val d'Orcia

schedule10 daysplan for pin_drop6stops directions_car~330 kmon the road flight_landFlorence (FLR)fly into

This Tuscany road trip is perfect for those who love food, history, and wine. Starting in Florence, you’ll spend two nights exploring the art and architecture of the city. Then, you’ll drive to Greve in Chianti for a night, where you can enjoy local wines and the beautiful countryside. The pace is relaxed, allowing you to savor each stop, like the medieval charm of Siena and the rolling hills of Pienza.

After two nights in Siena, you’ll head to Lucca for a night before returning to Florence for your final night. Each stop offers a chance to indulge in local cuisine and soak up the history of the region. This trip suits anyone looking to unwind while enjoying the best of Tuscany’s culture and flavors.

Florence
Day 1–3

Florence

2 nights · Travel guide
Explore the Uffizi Gallery, then visit the Duomo and enjoy local gelato.
Stroll through the historic center, savor Tuscan cuisine at a trattoria.
Things to do
Nearby: Uffizi Gallery · Florence Cathedral
Greve in Chianti
Day 3–4

Greve in Chianti

1 night · Travel guide
Drive the Chianti wine road, visit Radda for wine tasting and local food.
Things to do
Nearby: Chianti Wine Road · Radda in Chianti
Siena
Day 4–6

Siena

2 nights · Travel guide
Visit Piazza del Campo, enjoy local cuisine and wine in Siena.
Day trip to San Gimignano for towers and wine tasting, then explore Volterra.
Things to do
Nearby: Piazza del Campo · San Gimignano · Volterra
Day 6–8

Pienza

2 nights · Travel guide
Explore the Val d'Orcia, enjoy local cheese and wine in Pienza.
Visit Montepulciano for wine tasting and stunning views, then Montalcino.
Things to do
Nearby: Val d'Orcia · Montepulciano · Montalcino
Lucca
Day 8–9

Lucca

1 night · Travel guide
Walk the Lucca walls, enjoy a leisurely lunch and explore the town.
Things to do
Nearby: Lucca Walls
Florence
Day 9–10

Florence

1 night · Travel guide
Return to Florence, relax and enjoy a farewell dinner in the city.
Things to do
Make this trip yours →

from ~$1,203 p.p. · a rough estimate for flights and stays; you pick the real ones

The Kiomigo promise

Make this your route

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Change any stop, any stay, any day. Even mid-trip. Only your flights are fixed.

speedTravel at your pace

No group bus. No fixed program. Stay longer where it is good, skip what is not.

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Tick off what you dream of, not what the world expects.

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We travel with you and make memories together.

10 days · 6 stops from ~$1,203 p.p. Make it yours →