Tuscany

4 Day Itinerary for Tuscany: Florence, Chianti & a Hill Town

If you only have 4 days in Tuscany, focus on Florence and one countryside day. I’ve done this itinerary with friends visiting for the first time; it balances must-see attractions with local experiences.

Day 1 – Florence: First Glimpse of the Renaissance

I like to start my first morning in Florence early, before the crowds. Around 7:30 a.m., the streets around the Duomo are still quiet, and you can hear the echo of your footsteps on the stone. Grab a cappuccino and a cornetto at a standing-bar café (locals rarely sit) like one of the small bars along Via dei Servi.

Spend your first few hours simply walking: Duomo exterior, Piazza della Signoria, Ponte Vecchio. I usually save major museum visits for the afternoon. For lunch, slip into a trattoria in the Sant’Ambrogio area or the Oltrarno, away from the main thoroughfares. Try ribollita (Tuscan bread and vegetable soup) or pappa al pomodoro (thick tomato-bread soup).

In the afternoon, book timed entry to the Uffizi Gallery. The first time I visited, I spent too long trying to see everything and ended up exhausted. Now I focus on a few rooms—Botticelli, Leonardo, Michelangelo—and then take breaks by the windows overlooking the Arno.

End the day at Piazzale Michelangelo for sunset. I still remember my first walk up there—stopping halfway, breathless not from the climb but from seeing the whole city burn orange in the evening light. Families, couples, and groups of friends all gather here; buy a gelato from the kiosk and join them.

Day 2 – Florence: Art, Oltrarno & Local Life

On your second day, climb the Duomo’s cupola or the Campanile (bell tower). I prefer the Campanile: fewer crowds, stunning views, no netting at the top. Reserve ahead in 2026, as timed entries are increasingly required to control numbers.

Next, visit the Accademia Gallery to meet Michelangelo’s David. I was surprised the first time I saw him by how human he felt—veins, tension, the sense of movement. Go early or late to avoid the worst of the crowds.

Afternoon is for the Oltrarno, Florence’s “other side” across the river. Wander artisan workshops on Via Maggio and around Santo Spirito, where you can peek into leather studios, goldsmiths, and woodworkers. One of my favorite moments was stumbling into a tiny bookbinding studio and chatting with the owner about how his father taught him the craft.

In the evening, have an aperitivo in Piazza Santo Spirito or a wine bar on Via Santo Spirito. This is where Florence feels most local: kids playing, students chatting on the steps, neighbors greeting each other as they walk their dogs.

Day 3 – Chianti Wine Country

On day three of your 4 day itinerary for Tuscany, head into the countryside. Rent a car in Florence (I recommend picking it up at the airport or outskirts to avoid driving in the ZTL restricted city center) and drive towards Greve in Chianti, about 45 minutes away.

Greve’s central piazza is perfect for a mid-morning coffee and a visit to a historic butcher like Falorni for cured meats and cheeses. From there, follow the winding roads to Panzano in Chianti. The views from the terrace near the church are some of my favorites in the region.

Book a lunch and tasting at a small winery—many require reservations in 2026. I still remember a lunch at a family-run estate near Panzano: we sat at a long wooden table under a pergola, eating pici pasta with ragù, tasting Chianti Classico and olive oil while the owner’s dog napped in the shade.

Afternoon can be more winery visits (go slow!) or a gentle hike between vineyards. Families with kids will appreciate agriturismi that offer pools and space to run around while adults enjoy a glass of wine.

Either stay overnight in Chianti (recommended if you can add a night) or return to Florence in the early evening.

Day 4 – Siena or Pisa & Lucca (Choose Your Favorite)

For your last day, pick based on your interests:

• Siena: Medieval streets, dramatic Piazza del Campo, and a deep dive into Tuscan history.
• Pisa & Lucca: Iconic Leaning Tower paired with Lucca’s relaxed, family-friendly walled town.

If you choose Siena, take an early bus or train from Florence (or drive if you still have the car). Spend the day exploring the cathedral, climbing the Torre del Mangia, and people-watching in the main square.

If you choose Pisa and Lucca, start in Pisa in the morning, visit the Piazza dei Miracoli, then hop a short train to Lucca for an afternoon bike ride along the walls and dinner in one of its cozy trattorias.

5 Day Itinerary for Tuscany: Florence, Chianti & Siena

With 5 days in Tuscany, you can slow down a bit. Combine Florence with Chianti and Siena, or swap Chianti for Lucca if you prefer cities to vineyards.

Use the 4-day plan above as a base, then add:

• Extra Day in Chianti: Stay at an agriturismo, visit Castellina and Radda, enjoy a long countryside dinner under the stars.
• or Extra Day in Siena: Use Siena as a base for nearby hill towns like Monteriggioni and San Gimignano.

One of my favorite 5-day trips was three nights in Florence and two nights in a farmhouse near Castellina, where evenings were just us, crickets, and the glow of the distant town on the hill.

6 Day Itinerary for Tuscany: Florence, Chianti, Siena & San Gimignano

On a 6 days in Tuscany itinerary, you can add another classic hill town and some deeper countryside time. I like:

• 2 nights in Florence
• 2 nights in Chianti
• 2 nights in Siena (with a day trip to San Gimignano)

This split makes driving distances short and lets you experience city evenings, vineyard sunsets, and medieval piazzas after day-trippers have gone.

7 Day Itinerary for Tuscany: Florence to Val d’Orcia

A full 7 day itinerary for Tuscany lets you add the dreamy landscapes of Val d’Orcia. My ideal week-long trip looks like this:

• 2 nights in Florence
• 2 nights in Chianti or Siena
• 3 nights in Val d’Orcia (Pienza, Montalcino, or countryside agriturismo)

On my last 7-day trip, those three nights in Val d’Orcia were the highlight: misty mornings, empty roads, hot springs at twilight, and dinners where the owner came to our table to explain each dish.

1. Florence (Firenze)

Florence is where I fell in love with Tuscany. My first visit was in late October, when the air was cool enough for a light scarf and the crowds had thinned. I remember emerging from a narrow street into Piazza del Duomo and literally stopping in my tracks at the sight of that massive, striped cathedral.

Highlights & Things to Do:

• Duomo Complex: Cathedral, Baptistery, Cupola, and Campanile. Reserve a combo ticket in advance, especially in 2026 high season.
• Uffizi Gallery: Renaissance masterworks. Book timed entry, ideally late afternoon when groups have thinned.
• Accademia Gallery: Home to Michelangelo’s David—worth the hype.
• Oltrarno & Santo Spirito: Artisan workshops, local bars, and a more authentic feel.
• Boboli Gardens: Green escape with city views, especially nice with kids.

Food & Local Experiences:

Try a lampredotto sandwich from a street stall (tripe, but trust me—rich, comforting, very Florentine). Visit the Mercato Centrale for a crash course in Tuscan ingredients: wheels of pecorino, piles of seasonal produce, and butchers who will happily explain cuts in slow, patient Italian.

Tips: Florence is walkable. In 2026, ZTL (limited traffic zones) are strictly enforced, so park outside the center if you have a car. For families, consider staying near Piazza Santo Spirito or San Niccolò for quieter evenings and playground access.

2. Siena

I usually arrive in Siena by bus from Florence; the approach over rolling hills sets the tone. The first time I walked into Piazza del Campo, the shell-shaped square felt almost like a natural amphitheater carved into the city.

History & Significance: Siena was Florence’s rival in the Middle Ages, and you can still feel that pride in its 17 contrade (districts), each with its own symbol and colors. Twice a year they compete in the Palio, a bareback horse race around the Campo (2 July & 16 August).

Things to Do:

• Climb the Torre del Mangia for sweeping views over terracotta rooftops.
• Visit the Duomo with its striped marble façade and intricate floor mosaics (visible in certain months).
• Explore the Museo dell’Opera and the unfinished “new cathedral” façade for unique city views.

Personal Tip: One of my favorite Siena memories is ducking into a tiny wine bar in a side street off the Campo on a rainy afternoon. The owner poured local Vino Nobile and explained the Palio photos covering the walls—his contrada had just won.

3. San Gimignano

San Gimignano’s skyline of medieval towers looks like something out of a fantasy novel. I first visited on a hot June day; the stone lanes were busy, but stepping up a side alley, I found quiet corners with laundry flapping between windows and cats stretching in the shade.

What It’s Known For: Its 14 surviving towers (there used to be many more), saffron, Vernaccia white wine, and gelato that has literally won world championships.

Things to Do:

• Climb the Torre Grossa for views of vineyards and olive groves.
• Visit the Collegiata (cathedral) for frescoes that feel intimate, almost like storyboards.
• Take a short walk outside the walls at golden hour; the town glows, and day-trippers are gone.

Food Tip: Try a glass of Vernaccia with a plate of local pecorino cheese and honey at a wine bar on a side street rather than in the main square; it’s quieter and often cheaper.

4. Pisa

Pisa is more than a selfie with the Leaning Tower (though I’ve done that too, many times, usually trying to line up someone’s “holding up the tower” pose). The Piazza dei Miracoli is genuinely stunning: the white marble of the cathedral and baptistery against a bright green lawn.

Beyond the Tower: Wander along the Arno River, explore the studenty streets near the university, and look for small cafés where locals actually outnumber tourists. Pisa makes an easy half-day stop en route to Lucca or the coast.

Family Tip: Kids love climbing the tower (age/height restrictions apply). Reserve timed tickets well ahead in 2026; they often sell out in high season.

5. Lucca

Lucca is where I go when I want to exhale. The first time I stayed here, I rented a bike and did lazy loops along the tree-lined walls every evening as the sun went down, watching families stroll and elderly couples sit on benches chatting.

Things to Do:

• Rent bikes and ride the Renaissance walls (perfect for kids).
• Climb Torre Guinigi, the tower with oak trees on top.
• Visit Piazza dell’Anfiteatro, an oval piazza built on the site of a Roman amphitheater.

Why It’s a Great Base: Excellent train connections (Florence, Pisa, Viareggio), flat and walkable, with a relaxed vibe. Perfect for a car-free few days.

6. Val d’Orcia (Pienza, Montalcino, Montepulciano)

Val d’Orcia is where Tuscany becomes pure poetry. I still remember my first dawn drive here: mist pooled in the valleys, farmhouses floated like islands, and every turn revealed another Instagram-famous view—only better in person.

Pienza: Small, elegant town known for pecorino cheese and perfect proportions, redesigned in the Renaissance as an “ideal city.” Walk the via dell’Amore and via del Bacio (yes, “street of love” and “street of the kiss”) along the walls at sunset.

Montalcino: Hill town famous for Brunello wine. I once spent an entire rainy afternoon in a tiny enoteca here, tasting Brunello flights while the owner told stories about different vintages and harvests.

Montepulciano: Another lovely wine town, this one known for Vino Nobile. Its steep streets are a workout, but the views and cellars (some carved into the rock) are worth it.

Hot Springs: Nearby Bagno Vignoni and Bagni San Filippo offer thermal waters. Bagno Vignoni’s steaming pool in the main square is unforgettable on a chilly evening, even if you’re just watching from a café.

7. Chianti Region (Greve, Panzano, Castellina, Radda)

Chianti is not a single place but a swath of countryside between Florence and Siena. My happiest Tuscan days have often been here: driving narrow roads that snake between vineyards, stopping spontaneously at small wineries, and returning to a farmhouse for a sunset swim.

Greve: Market town with a triangular piazza, good for stocking up on picnic supplies.

Panzano: Famous for its charismatic butcher, Dario Cecchini, and beautiful valley views.

Castellina & Radda: Smaller, atmospheric hill towns with stone lanes and wine bars overlooking the countryside.

Activities: Wine tastings, vineyard walks, e-bike tours, cooking classes at agriturismi. Many farms welcome kids, with animals and gardens to explore.

8. San Quirico d’Orcia & Bagno Vignoni

San Quirico is one of those villages that rarely makes top-10 lists but quietly charms everyone who stops. I once spent a night here simply because my original plan fell through; it ended up being one of the most peaceful stays of the trip.

Nearby Bagno Vignoni is unique: the main square is dominated by a steaming thermal pool, fed by hot springs used since Roman times. Modern bathing facilities are in nearby spas, but just having an evening drink overlooking the misty water feels dreamlike.

9. Arezzo

Arezzo is one of my favorite hidden gems in Tuscany. Fewer tourists, rich art (Piero della Francesca frescoes), and a lovely main square, Piazza Grande, which hosts a big antiques fair monthly.

I visited during the September Giostra del Saracino, a medieval jousting festival. The whole town was in costume; drums, flags, and trumpets echoed through the streets. Even outside festival days, Arezzo feels refreshingly real and lived-in.

10. Cortona

Perched above the Val di Chiana, Cortona gained fame from “Under the Tuscan Sun,” but it’s still a pleasant, slightly quieter alternative to bigger names. The climb from the parking lot into town is steep, but the reward is sweeping views and mellow piazzas.

I once stayed just outside town in a farmhouse and would walk up each evening for gelato and a stroll, listening to the mix of Italian, English, and German in the air. It’s a good base if you want to dip into both Tuscany and neighboring Umbria.

11. Monteriggioni

Monteriggioni looks exactly like the fortified hill town children draw when asked to imagine a medieval castle: a perfect ring of walls and towers atop a hill. It’s small—you can walk through it in under an hour—but the sense of stepping back in time is palpable.

Come in the late afternoon when tour buses have gone. Have a glass of wine on the square, then walk a stretch of the walls for views over vineyards and olive groves.

12. Volterra

Volterra, with its Etruscan heritage and alabaster workshops, has a slightly wilder, wind-swept feel compared to other towns. The first time I visited, low clouds were racing over the hills and the city walls felt like the edge of the world.

Highlights include the Etruscan Museum, Roman theater ruins, and wandering narrow streets where artisans still carve alabaster by hand. It’s less crowded than San Gimignano and pairs well as a day trip from there or from the coast.

13. Maremma & Southern Coast

Maremma is Tuscany’s wild south: scrubby hills, cowboys (butteri), long sandy beaches, and fewer international visitors. I stayed once near the Parco della Maremma, hiking through pine forests to reach quiet stretches of beach where the only sound was the surf.

Food here leans more toward seafood and robust meat stews, and there’s a strong sense of rural identity. It’s a great add-on for repeat visitors who think they “know” Tuscany.

14. Elba Island

Technically still Tuscany, Elba Island feels like another world: turquoise water, rocky headlands, and little harbors. I took the ferry from Piombino one September; in shoulder season, the island is lively but not crowded.

Elba is perfect for swimming, snorkeling, coastal hikes, and lazy seafood lunches. Families love the shallow beaches; couples love the sunsets over the sea with a glass of local white wine.

15. Carrara Marble Mountains

The first time I saw the Apuan Alps from a distance, I thought they were snow-capped. They weren’t; it was marble. Visiting the Carrara quarries is one of the most unusual experiences in Tuscany—massive white gashes in the mountains, trucks looming like toys against the rock.

Guided tours take you into active quarries, explaining how marble has been extracted since Roman times and shipped all over the world. It’s a great counterpoint to Florence’s polished sculptures: here you see the raw material.

16. Casentino Valley & Sacred Forests

North-east of Arezzo, the Casentino valley is a green, forested region sprinkled with castles and monasteries. It’s ideal for hikers and those seeking spiritual retreats. I spent a rainy weekend here once, staying in a simple inn and hiking between chestnut woods and stone sanctuaries.

The Camaldoli and La Verna monasteries are peaceful places with deep Franciscan history. Even if you’re not religious, the quiet and the forest air are restorative.

17. Montepulciano

Montepulciano clings to a ridge, its streets sloping steeply up to the main square. I always feel like I’ve earned my wine tasting after climbing here. Cellars run deep under the palazzi; some open onto dramatic brick vaults and old oak barrels.

Try a glass of Vino Nobile di Montepulciano with a plate of crostini topped with liver pâté or melted pecorino. For families, the town’s many little shops and gelaterias make the climb more fun.

18. Montalcino

Montalcino, home of Brunello di Montalcino, has a slightly more reserved feel than some other hill towns. Wine is serious business here, but even if you’re not a connoisseur, the fortress, views, and surrounding vineyards are worth the trip.

One of my favorite Montalcino experiences was a late-afternoon tasting on a terrace as fog rolled into the valley below. It felt like being on an island above the clouds.

19. Pienza

Pienza is small but perfectly formed. Designed in the 15th century under Pope Pius II as an “ideal” Renaissance town, its main square and streets line up with almost mathematical grace. I like to arrive in the late afternoon, stroll the walls, and then sit on a bench overlooking the Val d’Orcia as the light fades.

The town smells faintly of cheese thanks to its famous pecorino. Step into a small shop, taste a few ages (fresh, semi-aged, aged), and buy a wedge for your next picnic.

20. Monte Argentario

On the southern coast, Monte Argentario is a rocky promontory connected to the mainland by sandbars. It’s rugged, with small coves, clear water, and winding roads. I drove here once in May—still quiet, with wildflowers along the roadside and almost-empty beaches.

Base in Porto Santo Stefano or Porto Ercole, rent a boat or take small ferries to nearby bays, and enjoy a very different side of Tuscany: seafood, sea breezes, and island views.