20 days in Italy Itinerary

20 days in Italy Itinerary

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Route & dates

20 days in Italy Itinerary

Start: Chicago
Fly + train:  15​h 45​min
1
Positano
— 4 nights
Drive:  1​h
2
Capri
— 2 nights
ferry + Drive:  2​h 30​min
3
Florence
— 2 nights
Drive:  2​h 30​min
4
Portofino
— 2 nights
Drive:  3​h 45​min
5
Montalcino
— 4 nights
Drive:  2​h 30​min
6
Rome
— 3 nights
Fly:  12​h 45​min
End: Chicago


Learn more about your trip

4
nights
Positano

Positano ©
Often referred to as the gem of the Amalfi Coast, Positano remains one of southern Italy's most sought-after vacation locales, thanks to its hillside location and picturesque, pastel buildings.
Your day-by-day itinerary now includes Franco's Bar as well as Bagni d'Arienzo. Get a sense of the local culture at Villa Cimbrone Gardens and Villa Rufolo. You'll explore the less-touristy side of things at Wine Tours & Tastings and La Masseria Farm.

To see ratings, maps, and other tourist information, read Positano online trip builder .

Chicago, USA to Positano is an approximately 16-hour combination of flight and train. Due to the time zone difference, you'll lose 7 hours traveling from Chicago to Positano. Prepare for somewhat warmer weather when traveling from Chicago in October: high temperatures in Positano hover around 72°F and lows are around 63°F. On the 7th (Mon), you'll have the morning to explore before heading off to Capri.

Things to do in Positano

Parks Tours Nightlife

Side Trips

Ravello, Wine Tours & Tastings, La Masseria Farm
Find places to stay Oct 3 — 7:
Highlights from your plan
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens
Villa Rufolo ©
Villa Rufolo
Franco's Bar ©
Franco's Bar

2
nights
Capri

Capri
The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
Gianni's Boat has been added to your itinerary. On the 7th (Mon), take a tour by water with Gianni's Boat. On the next day, kick back and relax at Marina Piccola and then don't miss a visit to Piazza Umberto I.

To see where to stay, reviews, photos, and other tourist information, refer to the Capri journey maker site .

You can drive from Positano to Capri in 3.5 hours. Expect a daytime high around 72°F in October, and nighttime lows around 63°F. Wrap up your sightseeing by early afternoon on the 9th (Wed) to allow time for travel to Florence.

Things to do in Capri

Outdoors Tours Museums

Side Trip

La Bottega dell'Arte di Sergio Rubino
Find places to stay Oct 7 — 9:
Highlights from your plan
Marina Piccola
Marina Piccola
Gianni's Boat ©
Gianni's Boat
Piazza Umberto I ©
Piazza Umberto I

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
You've now added Ponte Vecchio to your itinerary. Kick off your visit on the 9th (Wed): snap pictures at Ponte Vecchio.

To see where to stay, ratings, more things to do, and more tourist information, read our Florence trip planner.

Getting from Capri to Florence by combination of ferry and train takes about 5 hours. Other options: do a combination of ferry and car; or do a combination of ferry, flight, and train. Traveling from Capri in October, you can expect nighttime temperatures to be a bit cooler in Florence, with lows of 54°F. On the 11th (Fri), you'll have the morning to explore before heading off to Portofino.

Things to do in Florence

Wineries Historic Sites

Side Trips

Greve in Chianti, Ruffino - Tenuta di Poggio Casciano
Find places to stay Oct 9 — 11:
Highlights from your plan
Ponte Vecchio ©
Ponte Vecchio
Castello di Verrazzano ©
Castello di Verrazzano
Tenuta Riseccoli ©
Tenuta Riseccoli

2
nights
Portofino

Portofino ©
Portofino is an Italian fishing village and holiday resort famous for its picturesque harbour and historical association with celebrity and artistic visitors. You've now added Santa Margherita Ligure to your itinerary. Kick off your visit on the 11th (Fri): explore the historical opulence of Castello Brown and then go for a stroll along the water at Marina di Portofino. Get ready for a full day of sightseeing on the 12th (Sat): tour the pleasant surroundings at Baia del Silenzio and then wander the streets of Santa Margherita Ligure.

For reviews, ratings, traveler tips, and tourist information, read our Portofino trip planner .

Traveling by car from Florence to Portofino takes 2.5 hours. Alternatively, you can take a train; or take a bus. In October, daily temperatures in Portofino can reach 69°F, while at night they dip to 59°F. You'll have a few hours on the 13th (Sun) to wrap things up before traveling to Montalcino.

Things to do in Portofino

Parks Beaches Outdoors

Side Trips

Baia del Silenzio, Santa Margherita Ligure
Find places to stay Oct 11 — 13:
Highlights from your plan
Baia del Silenzio ©
Baia del Silenzio
Castello Brown ©
Castello Brown
Marina di Portofino ©
Marina di Portofino

4
nights
Montalcino

Montalcino ©
In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Eschew the tourist crowds and head to Ciacci Piccolomini d'Aragona and Decugnano dei Barbi. Do some cultural sightseeing at Podere Il Cocco and Mate Winery. Step out of Montalcino to go to Pienza and see Monticchiello, which is approximately 48 minutes away. There's still lots to do: do a tasting at Poggio Rubino, enjoy breathtaking views from Fortezza di Montalcino, and take in the spiritual surroundings of La Collegiata di San Quirico.

To find where to stay, reviews, and other tourist information, read our Montalcino travel planner.

Traveling by car from Portofino to Montalcino takes 4 hours. Alternatively, you can do a combination of train and bus; or take a bus. In October, plan for daily highs up to 73°F, and evening lows to 56°F. On the 17th (Thu), wrap the sightseeing up by early afternoon so you can drive to Rome.

Things to do in Montalcino

Wineries Historic Sites Neighborhoods

Side Trips

Decugnano dei Barbi, Monticchiello, La Collegiata di San Quirico
Find places to stay Oct 13 — 17:
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Podere Il Cocco ©
Podere Il Cocco
Poggio Rubino ©
Poggio Rubino

3
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Your itinerary includes some good beach time at Spiaggia di Torre Paola and V Lounge Beach Club. Explore hidden gems such as Santa Maria in Trastevere and Abbey of Saint Trinity. And it doesn't end there: admire the striking features of Pantheon, kick back and relax at Stabilimento Balneare le Palme, ponder the design of Trevi Fountain, and take a stroll through Trastevere.

To see maps, traveler tips, ratings, and more tourist information, use the Rome online trip builder .

Drive from Montalcino to Rome in 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. October in Rome sees daily highs of 73°F and lows of 55°F at night. Wrap up your sightseeing on the 20th (Sun) to allow time to drive to Siena.

Things to do in Rome

Beaches Parks Outdoors

Side Trips

Abbey of Saint Trinity, Spiaggia di Torre Paola, Il Pioniere
Find places to stay Oct 17 — 20:
Highlights from your plan
Pantheon ©
Pantheon
Trastevere ©
Trastevere
Trevi Fountain ©
Trevi Fountain

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