Why Tuscany
Use Florence as a base to explore cypress-lined hills, Brunello vineyards, medieval hill towns, and the thermal pools of the Val d'Orcia.
Key Facts
Top things to do
What you'll spend
Tuscany rewards a slow, uncrowded budget. Prices swing wildly with the season, and the countryside costs far less than Florence. Plan around three big line items, and the shoulder seasons keep the whole trip affordable.
Hotels
€120–€500 a night
Tastings
€15–€60 per person
Meals
€20–€70 per person
Tuscany's wineries and museums enforce strict booking and cancellation policies. Travel insurance helps you recover prepaid costs if plans change.
When to go
May and June bring wildflower hills, long light, and uncrowded wineries. September offers harvest buzz and warm weather. July and August turn the hill towns hot and packed, while winter is quiet, chilly, and beautiful.
How to arrive
Fly into Florence's Amerigo Vespucci (FLR) for the shortest drive to the countryside, or Rome's Fiumicino (FCO) for wider flight choices and the fast Frecciarossa train north. From either, take the high-speed rail to Florence's Santa Maria Novella station, then pick up a rental car for the hill towns and wineries.
- Fly into Florence's Amerigo Vespucci (FLR) or Rome's Fiumicino (FCO)
- Ride the high-speed Frecciarossa train to Florence's Santa Maria Novella station
- Rent a car at the station for the hill towns and wineries
Moving around the region
A rental car unlocks the countryside: Chianti's winding wine roads, San Gimignano's hilltop approach, and the cypress lanes of the Val d'Orcia. Regional trains link Florence and Siena without parking hassles, and every walled town is best explored on foot across its cobbled streets.
- Rent a car for the hill towns and wineries
- Take regional trains between Florence and Siena
- Walk the walled towns; parking is outside the gates
Plan your visit
-
Rent a car to reach hill towns and wineries that public transport barely serves
-
Book Brunello tastings and Florence museum tickets at least a week ahead
-
Park outside medieval walls; ZTL cameras fine cars that enter historic centers
-
Pack layers; hill towns stay cooler than Florence and evenings turn chilly
Where to base yourself
Choose a city base for culture or a country farmhouse for slow mornings.
Where to eat
Osterias, gelato in a medieval piazza, and Brunello poured from ancient cellars.
Dress for the region
Layers carry the day: hill towns run cooler than Florence and evenings turn chilly even in summer. Comfortable shoes matter most for cobbled streets and steep lanes, and wineries want smart casual rather than hiking gear. Pack light linens for midday sun and a light jacket for evenings.
Capturing your trip
Point the lens at the Val d'Orcia's cypress-lined roads in the last hour of light, when the hills glow gold. Shoot San Gimignano's towers at dawn before crowds fill the lanes, and climb Siena's Torre del Mangia for the Piazza del Campo's fan-shaped sweep at its quietest.
Getting around with ease
Tuscany's hill towns are steep and cobbled, and San Gimignano and Siena involve real climbing. Historic centers sit inside ZTL traffic limits, so driving in is restricted and fines are steep. A car is essential for reaching rural wineries, and ground-floor agriturismi rooms are the easiest base.
The honest take
Unforgettable landscapes with summer crowds, slow roads, and booked-out tastings.
-
July and August pack Florence, Siena, and San Gimignano wall to wall
-
Country roads are winding and slow; always add time to drive anywhere
-
Popular Brunello tastings and town restaurants book out days ahead