Italian Grand Tour: Ligurian Coast to Tuscany

Ten days sweeping from the colourful harbours of Genoa and Portofino through the clifftop villages of Cinque Terre, then deep into Tuscany — Renaissance Florence, Chianti vineyards, the dreamy Val d'Orcia, and a final flourish in Rome and Bologna.

Aja Bunta

@buntaaja · creator's guide

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24 stops · 751 mi · 19h 19m on the road

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1

Arrival: Boccadasse, Bogliasco & glamorous Portofino

4 stops

Ease into the trip with a gentle coastal drive from Genoa's bohemian cove to the pastel perfection of Portofino, ending the evening in La Spezia — your base for Cinque Terre.

AFTERNOON

Spiaggia di Boccadasse

Genoa

A crescent of colourful fishing boats and gelato-hued houses — the perfect soft landing. Parking nearby is tricky; expect a short walk, but the first Aperol spritz of the trip makes it worthwhile.

5.8 mi · 11m

AFTERNOON

Bogliasco

Bogliasco

A charming coastal village worth a brief stop. Parking is easy here — a rare luxury on this stretch of coast.

14 mi · 26m

EVENING

Viewpoint Portofino

Portofino

Castello Brown Ticket costs 10 euros, the last entry was at 18:30, closing time at 19:00. We parked at Parcheggio Piazza della Liberta (the only parking) - it is quite expensive (more then 50e for 3 hours), but we stayed only 1 hour.

53 mi · 1h 2m

La Spezia

La Spezia

La Spezia makes a practical and pleasant base — well-connected by train to all five Cinque Terre villages for the day ahead.

2

Cinque Terre: Vernazza to Riomaggiore

7 stops

Four of the five villages in one memorable day — best tackled by train or Vespa to skip the limited parking and steep approach roads.

Vernazza

Vernazza

Walk straight to the pier end for the classic harbour shot framed by pastel towers. The village centre is a no-drive zone; parking is about 1 km uphill from town.

11 mi · 3h 57m

AFTERNOON

Doria Castle

Porto Venere

A 15-minute uphill walk rewards you with a full panoramic sweep over Vernazza's rooftops and the Ligurian sea — one of the best viewpoints in all of Cinque Terre.

21 mi · 29m

Corniglia

Vernazza

The only village you can actually drive into, which makes it a relaxed stop for a coffee, a light lunch, and — naturally — the first Aperol spritz of the afternoon.

7.4 mi · 10m

Manarola

Riomaggiore

Stroll the narrow lanes and iconic harbour of one of Cinque Terre's most photogenic villages before heading up to Nessun Dorma.

0.2 mi · 1m

Nessun Dorma

Manarola

The food is decent rather than exceptional, but the terrace view over Manarola is breathtaking. Reserve a time slot in advance — you cannot order drinks only. Worth knowing: a short walk up the path gives you nearly the same panorama for free.

4.1 mi · 6m

MORNING

Riomaggiore

Riomaggiore

Riomaggiore's stacked coloured houses glow in the evening light — a perfect spot to linger and watch the sun drop into the sea.

9.9 mi · 14m

La Spezia

La Spezia

Back to La Spezia for a well-earned dinner and rest after a full day on the trails and waterfront.

3

Beach day in Monterosso al Mare

1 stop

A full day on the sandy beach of Monterosso, the largest Cinque Terre village, with Aperol Spritz on the shore.

AFTERNOON

Monterosso al mare Beach

Monterosso al Mare

Monterosso is the largest and sandiest of the five villages — the one place in Cinque Terre where a proper beach day is actually possible. Claim a spot, order an Aperol Spritz, and let the morning drift by.

4

Arrival in Florence & sunset at Piazzale Michelangelo

1 stop

Arrive in Florence and explore the city — wander to Piazzale Michelangelo for a sweeping sunset view over the Arno.

EVENING

Piazzale Michelangelo

Florence

The classic introduction to Florence: a sweeping terrace view over the Arno, the Duomo, and the terracotta rooftops that seem to stretch to the horizon. Arrive before golden hour for the best light.

5

Florence: Renaissance streets & city life

1 stop

Full day in Florence — soak up the Renaissance architecture and lively streets.

AFTERNOON

Florence

Florence

A full day to lose yourself in one of the world's great cities — world-class museums, medieval streets, and trattorias that reward wandering without a fixed plan.

6

Chianti wine country & a legendary Florentine steak

3 stops

Drive through the Chianti hills, visiting Castellina in Chianti and Greve in Chianti with a Florentine steak feast.

AFTERNOON

Greve in Chianti

Greve in Chianti

The main market town of Chianti — browse the butchers and wine shops around the central piazza before the afternoon drive south.

18 mi · 21m

AFTERNOON

Castellina in Chianti

Castellina in Chianti

A compact hilltown of Etruscan origin with an underground Etruscan road carved through the rock, wine cellars, and views over vine-covered slopes.

13 mi · 25m

Antica Macelleria Cecchini

Greve in Chianti

Dario Cecchini is Italy's most celebrated butcher — a theatrical, larger-than-life figure whose Panzano shop is a pilgrimage for carnivores. Book ahead and come hungry for a Florentine steak to remember.

7

Siena & the Crete Senesi near Asciano

2 stops

The order of stops runs Siena first, then Asciano — a morning in the medieval city followed by an afternoon in the sculpted clay hills of the Crete Senesi.

AFTERNOON

Siena

Siena

Siena's shell-shaped Piazza del Campo and soaring Gothic Duomo are among the finest medieval streetscapes in Europe — allow at least half a day to do them justice.

23 mi · 27m

MORNING

Asciano

Asciano

The rolling clay badlands of the Crete Senesi around Asciano are hauntingly beautiful — bare ridgelines, isolated farmhouses, and a colour palette that shifts with the afternoon light.

8

Pienza & the Val d'Orcia

2 stops

Iconic cypress-lined roads around Pienza and drone views over the rolling Val d'Orcia landscape.

MORNING

Pienza Cypress Avenue

Pienza

The cypress-lined avenue near Pienza is one of Tuscany's most iconic images — arrive early to have it to yourself, and bring a drone if you have one.

0.8 mi · 3m

AFTERNOON

Pienza

Pienza

A Renaissance jewel perched on a ridge above the Val d'Orcia. The compact historic centre — a UNESCO World Heritage Site — is easily explored on foot in a couple of hours.

9

A day in Rome

1 stop

Day in Rome exploring the city before the journey home.

AFTERNOON

Rome

Rome

One day is never enough, but Rome rewards even a brief visit — ancient ruins, baroque piazzas, and the kind of street-level energy that is impossible to replicate anywhere else.

10

Monteriggioni's medieval walls & Bologna

2 stops

Stop at the perfectly preserved medieval walls of Monteriggioni, then travel north to Bologna.

MORNING

Monteriggioni

Monteriggioni

Monteriggioni's perfectly intact ring of medieval towers rises from the Tuscan plain exactly as Dante described it in the Inferno — a quick but genuinely striking stop on the road north.

100 mi · 1h 58m

AFTERNOON

Bologna

Bologna

Bologna closes the trip on a high note: arcaded medieval streets, Europe's oldest university, and a food culture — tortellini, mortadella, ragù — that justifies the city's nickname, La Grassa.