The Perfect 10-Day Itinerary in Tuscany: Exploring towns, Hidden Gems & Travel Tips
Planning a Tuscany trip? This 10-day Tuscany itinerary covers Florence, Siena, San Gimignano, Val d’Orcia, and more with travel tips, routes, and must-see stops.
3/31/20263 min read
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If Tuscany has been sitting on your Pinterest board for years… same! It’s one of those places that somehow looks even better in real life—rolling hills, vineyards, golden sunsets, and those tiny hilltop towns that feel frozen in time.
The tricky part? Figuring out how to see it all without rushing.
So if you’re planning a trip and want a mix of iconic spots and those dreamy countryside moments, this 10-day Tuscany itinerary is exactly what I’d recommend.
Quick Tips Before You Go
Rent a car (you’ll thank me later)
Stay in 2–3 home bases instead of moving every night
Plan for calm mornings & slow days - no rushing
Day 1–3: Florence (Your Starting Point)
You have to start in Florence. It’s the heart of Tuscany and where most flights/train routes connect. And why not? It may be a busy city, but it's absolutely remarkable, so don't skip it!
Spend your first few days easing into the trip:
Walk across Ponte Vecchio at sunset
Visit the Duomo (yes, it’s worth it)
Eat your weight in pasta + gelato
Wander with no plan (this is where Florence shines)
Pro tip: Book tickets for museums ahead of time—this is the busiest stop of your trip.
Day 4: Pisa + Lucca (Easy Day Trip Combo)
Pick up your rental car and head out.
Stop in Pisa for the iconic leaning tower photo (quick stop is enough)
Then head to Lucca (pictured below), one of Tuscany’s most underrated towns
Lucca is quieter, charming, and perfect for:
Biking along the city walls
Long, relaxed lunches in hidden piazzas
Day 5: San Gimignano + Chianti
This is where Tuscany starts to feel like a movie.
Morning in San Gimignano (aka the “medieval Manhattan” with its towers)
Afternoon drive through Chianti wine region
Things to do:
Stop at a vineyard (don’t over-plan—just pull over somewhere scenic)
Wine tasting + countryside views
Sunset over vineyards (core memory moment)
Day 6–7: Siena (Your Second Base)
Head to Siena, one of the most beautiful medieval cities in Tuscany.
Explore Piazza del Campo
Climb Torre del Mangia (views are insane)
Get lost in the narrow streets
Siena is often listed as one of the top must-visit towns in Tuscany alongside Florence and Pisa, but it feels way less overwhelming.
Stay here 2 nights so you can slow down.
Day 8–9: Val d’Orcia (The Tuscany You See on Instagram)
Now for the dreamiest part of the trip…
Drive into Val d’Orcia, a UNESCO-listed region famous for its landscapes .
Base yourself near:
Pienza
Montepulciano (Pictured below)
Must-do stops:
Cypress tree roads
Pecorino cheese in Pienza
Sunrise or sunset drives (trust me on this)
This is where you’ll want to do less and feel more.
Day 10: Cortona or Arezzo + Return
On your last day:
Visit Cortona (very “Under the Tuscan Sun” vibes)
Or stop in Arezzo (pictured below) for a quieter, local feel
Then head back toward Florence for departure.
Best Towns to Include
If you’re building your own version of this itinerary, these are consistently the most searched and recommended towns:
Florence (top search + main hub)
Siena
San Gimignano
Pisa
Montepulciano
Pienza
Lucca
Why Tuscany?
The biggest mistake people make in Tuscany? Trying to do too much.
This isn’t a “check everything off” destination. It’s a:
sit longer
drive slower
order another glass of wine kind of place
If you follow this 10-day Tuscany itinerary, you’ll get a little bit of everything—iconic cities, countryside magic, and those random, unplanned moments that end up being your favorite part.
