1Florence
FirenzeThe Renaissance, still breathing.
Best overallWhy buy
- Postcard scenery
- Great value
- Incredible food
Keep in mind
- Crowded in season
- Short best window
$09.6
Rank #1Loading page
The 7 Best Towns in Tuscany
Hill towns, vineyards and the eternal question: Florence or Siena?
Amina DialloGlobal Travel & Nature EditorUpdated 6mo ago 432K reads
Verified
Winner
Florence
Overview
Tuscany is the world's most argued-over region, and the argument is always the same: which town deserves your three days? We drove 900 kilometres of cypress-lined roads to settle it — spoiler: the answer is several of them.
Winner spotlight
And the winner is…
№1Florence
by FirenzeFlorence wins because it contains multitudes: a Renaissance city, a food capital, and a basecamp for day trips that means you never have to choose. The Duomo at dawn, the markets at noon, the sunset from Piazzale Michelangelo — it's a greatest hits album that never dips.
Best overall$0
At a glance
Quick comparison
| Pick | #1 Florence $0 | #2 Val d'Orcia $0 | #3 Siena $0 | #4 San Gimignano $0 | #5 Lucca $0 | #6 Montepulciano $0 | #7 Cortona $0 |
|---|---|---|---|---|---|---|---|
| Score | 9.6 | 9.5 | 9.4 | 9.2 | 9.0 | 8.9 | 8.8 |
| Scenery | Iconic | Stunning | Beautiful | Lovely | Charming | Nice | Nice |
| Crowd level | Manageable | Moderate | Busy | Busy | Quiet | Quiet | Quiet |
| Food scene | World-class | Excellent | Great | Great | Good | Good | Good |
| Best season | Spring | Autumn | Spring | Autumn | Summer | Spring | Autumn |
The list
The top 7, ranked
Ordered by overall score across every test. The “best for” note tells you exactly who each pick is for.
1
2Val d'Orcia
SienaThe landscape you've already dreamed of.
SceneryWhy buy
- Easy to reach
- Fewer crowds
- Photogenic at every hour
Keep in mind
- Pricier than expected
- Over-touristed
$09.5
Rank #2
3Siena
SienaThe most perfect square in Italy.
AtmosphereWhy buy
- Great value
- Incredible food
- Worth the detour
Keep in mind
- Hard to reach
- Needs a car
$09.4
Rank #34San Gimignano
SienaMedieval skyline, world-famous gelato.
PostcardsWhy buy
- Fewer crowds
- Photogenic at every hour
- Postcard scenery
Keep in mind
- Short best window
- Weather dependent
$09.2
Rank #4
5Lucca
LuccaRide a bike along the city walls.
Easy livingWhy buy
- Incredible food
- Worth the detour
- Easy to reach
Keep in mind
- Over-touristed
- Crowded in season
$09.0
Rank #5
6Montepulciano
SienaVino Nobile and hilltop drama.
WineWhy buy
- Photogenic at every hour
- Postcard scenery
- Great value
Keep in mind
- Needs a car
- Pricier than expected
$08.9
Rank #6
7Cortona
ArezzoUnder the Tuscan Sun, without the crowds.
Quiet escapeWhy buy
- Worth the detour
- Easy to reach
- Fewer crowds
Keep in mind
- Weather dependent
- Hard to reach
$08.8
Rank #7Deep dive
Feature matrix
| Feature | Florence | Val d'Orcia | Siena | San Gimignano | Lucca | Montepulciano | Cortona |
|---|---|---|---|---|---|---|---|
| Accessible by train | |||||||
| Budget friendly | |||||||
| Hidden gems | |||||||
| Photogenic | |||||||
| Family friendly | |||||||
| Local food scene | |||||||
| Guided tours | |||||||
| Quiet escape |
The verdict
Pros & cons
What we love
- Food that justifies the entire flight
- Drivable, scenic, and compact
- Wine at cellar-door prices
- Spring and autumn are perfect
Watch out for
- July and August are an oven
- Florence crowds are legendary
- A car is near-essential
- Parking is a blood sport
Before you buy
Buyer's guide
Every destination was visited in person by our editors, in season, for a minimum of three days. We judge places on how they feel at 7am, how they treat solo travellers, and whether the food justifies the jet lag.
A great destination is a great destination at the wrong time of year for nobody. Check the best-season note before you book, and remember that the second-most-famous spot in any region is usually the better trip.
Rent the smallest car you can physically fit in — Tuscan streets were designed for carts, not SUVs. Stay in a farmhouse outside the walls for the first half, a town centre for the second.
The winner of our The 7 Best Towns in Tuscany ranking is the pick that scored highest across every test — but 'best overall' isn't always 'best for you'. Use the 'Best for' note under each of the seven to match a pick to your budget, your space and your habits. Every entry on this list earned its place; the ranking simply tells you where to start.
Questions
Frequently asked
We don't pretend to be objective — we're transparent. Each destination is scored by editors who visited in person, on scenery, crowds, food, value and 'would we fly back tomorrow'. The score is an average of those five.
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