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Tuscany

Roadtrip through

Tuscany

CULTUREROAD TRIPNATURE7 days

Renaissance cities, hill towns and hot springs across Tuscany

Dosage

7 days

Indication

Art, wine, food & landscape

Contra-indication

Peak season

Side effects

Considering a move to the Tuscan countryside

Roadtrip through  why go

This 7 day Tuscany itinerary combines Florence and Siena with the hill towns, vineyards and countryside of southern Tuscany. Start with Renaissance Florence, then pick up a car for the scenic roads through Chianti and Val d’Orcia, with stops for long lunches, small villages, thermal springs and one very specific reason to detour to Panzano.

✦  Based on expert opinion: We did the trial and error, so you get the optimized route.

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At a glance

Dosage7 days
IndicationArt, wine, food & landscape
Contra-indicationPeak season
Side effectsConsidering a move to the Tuscan countryside

The itinerary  what to do, where

6 places

The route

Florence - Day 1-2

Two days of Renaissance art, narrow streets, good food and views over Florence from the hills above the city.

Stay: Hotel Signoria ’64 — right in the historic centre, within the pedestrianised zone.
Getting there: International flight to Florence (FLR). The tram from the airport into the city centre is straightforward and takes around 20 minutes.

Highlights

  1. The Duomo
  2. Uffizi Gallery (free entry 1st Sunday of the month)
  3. Ponte Vecchio — known for its jewellery shops.
  4. Leather market
  5. San Miniato al Monte — worth the climb for both the church and the view over Florence.
  6. Piazzale Michelangelo
  7. Rooftop bar at sunset or night (many options)

Getting aroundOn foot.

EatIl Grande Nuti — fresh pasta.Trattoria Dall’Oste — Florentine steak.Anzuini — all-day Italian style snacks.

CoffeeDitta Artigianale — also good for breakfast.

TipQueues for The Duomo can be very long, visit early (check opening hours)
Florence - Day 1-2
View from Piazzale Michelangelo

Siena & the Chianti Road - Day 3

This is where the trip shifts from city break to road trip: hill views, winding roads and a compact medieval centre once you reach Siena.

Stay: Residenza d’Epoca San Martino 29 — historic rooms in central Siena.
Getting there: Collect a hire car in Florence and take the SR222 through Chianti.

Highlights

  1. Piazza del Campo
  2. Siena Cathedral
  3. Note del Chianti perfume shop— Best perfume we've ever had and worth visiting for the shop experience itself.

Getting aroundSiena’s historic centre is largely car-free; use the hotel’s parking arrangement outside the city walls.

TipIf you want to add another Tuscan town, detour via San Gimignano on the way to Siena.
Siena & the Chianti Road - Day 3
Scenic stop on the SR222 route

Val d’Orcia - Day 4

A slower countryside day of hill towns, vineyard views and short stops rather than major sights. Golden hour is spectacular in these villages.

Stay: Villa Nottola — the rooms are traditional rather than luxurious, with an old-fashioned feel that suits the setting. The real draw is the beautiful vineyard estate surrounding the property.
Getting there: Rental car - aorund 1.5 hours

Highlights

  1. Montalcino
  2. Pienza (near one of the best-known Gladiator filming locations)
  3. Montepulciano
TipDo not try to turn every hill town into a full sightseeing stop. Pienza and Montalcino work well as places to wander, eat and enjoy the surrounding views.
Val d’Orcia - Day 4
Sunset at Montepulciano

Saturnia - Day 5

Swap hill towns for thermal water and a slower day in the Tuscan countryside.

Stay: Terme di Saturnia Natural Spa & Golf Resort
Getting there: Continue your road trip by car

Highlights

  1. Cascate del Mulino di Saturnia - walkable from the hotel
  2. The drive through the Tuscan countryside

EatLa Stellata Country Restaurant: a golf cart takes you

TipVisit Cascate del Mulino around sunrise if you want to avoid the larger daytime crowds.
Saturnia - Day 5
Terme di Saturnia

Panzano in Chianti - Day 6

A small Chianti stop built around one meal rather than a long sightseeing list.

Stay: Villa Il Tinaio — reached by a steep, narrow road, but worth it for the views.
Getting there: 2.5 hours - breaks the distance back to Florence

Highlights

  1. Wine tasting in Panzano in Chianti
  2. Antica Macelleria Cecchini (Dario Cecchini) — the reason we added Panzano to the route.

EatAntica Macelleria Cecchini — book dinner far ahead!

Panzano in Chianti - Day 6
Dario Cecchini (from Netflix Chef's Table)

Departure (Florence) - Day 7

Return to Florence for the flight home and leave the last part of the trip deliberately light.

    TipIf you have one extra day, either keep it free in Florence or take the train to Bologna (37 minutes). Book ahead for better fares (around €30).
    Departure (Florence) - Day 7
    Cattedrale di Santa Maria del Fiore

    From the road  9 photographs

    Before you go  take it with you

    Make Tuscany your next story

    Questions about timings, seasons, or where to swap a stop? Write to us — we answer every message with the map open.

    Plan it with us

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