Italy in 10 Days: Venice, Cinque Terre, Florence, Chianti, Positano, Capri and Rome

Before we got married in Tuscany, there was this trip: ten days in August 2021 that took us from top to bottom of Italy. It’s a lot of ground to cover, and we’d do it again in a heartbeat. This is the trip that made us fall in love with the country.

Who came: Just Colin and me
Route: Venice → Cinque Terre → Florence → Chianti → Positano and the Amalfi Coast → Capri → Rome
How long: 10 days
Best for: A first trip to Italy that hits the classics

Venice

We started in Venice with gondolas and boats on the Grand Canal, the green dome of San Simeone Piccolo, and the Bridge of Sighs lit up at night. On our last morning we said goodbye to the city from the water at sunrise.

The Grand Canal with a green-domed church and pastel palazzos under a blue sky — Gondola traffic, domes, and that impossible Venetian blue

The Bridge of Sighs lit up over a dark canal at night

A couple standing on a bridge with colorful buildings along the Grand Canal behind them

A man standing on a small canal bridge with an iron railing and pink buildings

A couple taking a selfie on a boat on the Grand Canal in early morning light

Cinque Terre

Next were the five cliffside villages of the Cinque Terre. We hiked the coastal trail between them, watched the sunset from the rocks in Riomaggiore with what felt like the whole town, and found rows of striped beach umbrellas in Monterosso.

Riomaggiore's colorful houses stacked above a rocky harbor — Riomaggiore: the most photogenic pile of houses in Italy

People gathered on the rocks below Riomaggiore's pastel buildings at sunset

A man standing on breakwater rocks near Vernazza beneath dramatic clouds

A couple taking a selfie on a hiking trail high above the sea

Rows of blue and white beach umbrellas along a Ligurian beach

Florence

In Florence we ate cappuccinos and croissants for breakfast, got lost in cobblestone side streets, saw the marble front of Santa Croce, walked along the Arno, and climbed up for the sunset view over the Duomo.

The white marble Gothic facade of the Basilica of Santa Croce

A couple posing at a hilltop overlook above the Florence rooftops

A cappuccino next to a tray of flaky croissants

A woman walking down a narrow cobblestone street between stone buildings

The sun setting over Florence's rooftops and hills

Chianti

Then we went out into the hills of Chianti, between Florence and Siena: vineyards and cypress trees, stone hill towns like Greve and Radda, glasses of Chianti Classico, and a pool looking out over the hills.

Two glasses of red wine on a table overlooking Tuscan hills

A Tuscan villa and a line of cypress trees at sunset

A stone lane with an arch and old buildings in a hill town

A couple taking a selfie with cypress trees and green hills behind them

Positano and Capri

Down south on the Amalfi Coast, Positano was every bit the postcard, with boats packed into the harbor below houses stacked up the cliff. From there we took a boat to Capri, where we spent a day on the water swimming under the limestone cliffs, then wandered through the lemon trees.

Boats crowding the harbor below the colorful cliffside town of Positano — Positano, where even the boats look glamorous

Capri's dramatic limestone cliffs rising from a deep blue sea — Capri from the water: unreal

Positano's hillside houses seen from a departing boat, with a 'Bye Positano, next stop Capri' caption

Looking down on Capri's Marina Grande and the turquoise coastline

Swimmers in clear water beneath a towering limestone cliff

Rome

We ended in Rome with the greatest hits: the Colosseum, the Vittoriano, quiet back streets, the Trevi Fountain by day and by night (coin tossed, so we had to come back), and the Tiber glowing after dark.

A couple standing in front of the Colosseum on a sunny afternoon — Checked off: the Colosseum

A couple at the illuminated Trevi Fountain at night

The white marble Vittoriano monument under a blue sky

The Tiber River at night reflecting a lit bridge

A woman walking down a quiet street lined with ochre buildings

Tips for this route

Take the train. Venice, La Spezia, Florence and Rome are all connected by fast trains.
Rent a car only for Chianti. It’s the one stop where a car really helps.
Use the ferries on the Amalfi Coast. They’re faster than the road in August.
August is hot and busy. Start early and book stays ahead.

We came back to Italy again and again, and got married there in 2024. Read our favorite corners of Italy and our Tuscany wedding.