20 days in Italy Itinerary

20 days in Italy Itinerary

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Route & dates

20 days in Italy Itinerary

Start: New York City
Fly:  13​h 15​min
1
Rome
— 2 nights
Drive:  3​h 15​min
2
Positano
— 2 nights
bus:  30​min
3
Ravello
— 3 nights
Drive:  4​h 30​min
4
Assisi
— 1 night
Drive:  2​h 15​min
5
Florence
— 2 nights
train:  2​h 15​min
6
Venice
— 2 nights
Drive:  3​h 30​min
7
Siena
— 3 nights
Drive:  3​h 15​min
8
Verona
— 3 nights
Fly + bus:  13​h
End: New York City

2
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 cultural itinerary includes sights like Colosseum and Pantheon. Your inner history buff will appreciate St. Peter's Basilica and Vatican Museums. There's much more to do: explore the ancient world of Palatine Hill, browse for treasures at Serra, contemplate the long history of Roman Forum, and wander the streets of Trastevere.

To find ratings, more things to do, reviews, and other tourist information, read Rome trip planning website .

New York City, USA to Rome is an approximately 13.5-hour flight. You can also do a combination of bus and flight; or do a combination of train and flight. The time zone changes from Eastern Standard Time (EST) to Central European Time (CET), which is usually a 6 hour difference. In June, daily temperatures in Rome can reach 84°F, while at night they dip to 65°F. Wrap up your sightseeing on the 9th (Tue) early enough to drive to Positano.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trip

Vatican City
Highlights from your plan
St. Peter's Basilica ©
St. Peter's Basilica
Colosseum ©
Colosseum
Pantheon ©
Pantheon

2
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.
Start off your visit on the 10th (Wed): take in the spiritual surroundings of Church of Santa Maria Assunta, enjoy the sand and surf at Fornillo, then stop by Nana' Positano, and finally stroll through Bagni d'Arienzo Beach Club, Positano. On the next day, get to know the fascinating history of Il Vallone dei Mulini, take in the spiritual surroundings of St Francis Church and Convent, and then take a memorable tour with Tours.

To plan Positano vacation without wasting time, ask Inspirock to design an itinerary.

Getting from Rome to Positano by car takes about 3.5 hours. Other options: do a combination of train and subway; or take a bus. In June, plan for daily highs up to 82°F, and evening lows to 68°F. Finish your sightseeing early on the 11th (Thu) so you can take a bus to Ravello.

Things to do in Positano

Outdoors Parks Wildlife

Side Trip

Sorrento
Highlights from your plan
Fornillo ©
Fornillo
Fishing Charters & Tours
Church of Santa Maria Assunta ©
Church of Santa Maria Assunta

3
nights
Ravello

Ravello ©
Deepen your sense of the past at sights like Duomo di Ravello and Duomo di Sant'Andrea. Escape the urban bustle at Lido di Ravello and Lido Capo di Conca.

To find other places to visit, ratings, reviews, and more tourist information, you can read our Ravello trip itinerary planning website .

Ravello is just a stone's throw from Positano. June in Ravello sees daily highs of 79°F and lows of 72°F at night. Finish your sightseeing early on the 14th (Sun) so you can drive to Assisi.

Things to do in Ravello

Parks Outdoors Beaches

Side Trips

Amalfi, Lido Capo di Conca
Highlights from your plan
Spiaggia di castiglione ©
Spiaggia di castiglione
Lido di Ravello ©
Lido di Ravello
Duomo di Ravello ©
Duomo di Ravello

1
night
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
On the 15th (Mon), examine the collection at Museo della Porziuncola, take in the spiritual surroundings of Basilica di Santa Maria degli Angeli - Porziuncola, pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, then contemplate in the serene atmosphere at Basilica di Santa Chiara, then take in the spiritual surroundings of Eremo delle Carceri, and finally explore the historical opulence of Rocca Maggiore.

Plan a Assisi trip in moments using our itinerary builder.

You can drive from Ravello to Assisi in 4.5 hours. Alternatively, you can take a train; or do a combination of bus and train. Expect little chillier evenings in Assisi when traveling from Ravello in June, with lows around 60°F. Wrap up your sightseeing on the 15th (Mon) to allow time to drive to Florence.

Things to do in Assisi

Historic Sites Museums
Highlights from your plan
Museo della Porziuncola ©
Museo della Porziuncola
Eremo delle Carceri ©
Eremo delle Carceri

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Kick off your visit on the 16th (Tue): examine the collection at Academy Of Florence Art Gallery, view the masterpieces at M.G. Design, then get to know the fascinating history of Piazza del Duomo, then pause for some serene contemplation at Cathedral of Santa Maria del Fiore, and finally admire the masterpieces at Gallerie Degli Uffizi. Get ready for a full day of sightseeing on the next day: stroll through Lido Di Camaiore, don't miss a visit to Piazza della Signoria, and then take a memorable tour with Tours.

For where to stay, photos, maps, and other tourist information, read Florence day trip app .

Drive from Assisi to Florence in 2.5 hours. Alternatively, you can take a train. In June, plan for daily highs up to 83°F, and evening lows to 65°F. Finish your sightseeing early on the 17th (Wed) so you can take a train to Venice.

Things to do in Florence

Outdoors Museums Beaches
Highlights from your plan
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Cathedral of Santa Maria del Fiore ©
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi

2
nights
Venice

Venice ©
Virtually unchanged for the last six centuries, Venice is actually a group of islands made famous by a series of canals, bridges, monuments, piazzas, and narrow pedestrian lanes.
Start off your visit on the 18th (Thu): appreciate the extensive heritage of Piazza San Marco, then take in the exciting artwork at Contini Art Gallery, and then explore the activities along Canal Grande. On the 19th (Fri), you'll have a packed day of sightseeing: admire the landmark architecture of Doge's Palace, admire the landmark architecture of Basilica di San Marco, then wander the streets of Campo del Ghetto, then get a taste of the local shopping with Segni nel Tempo antiquarian bookshop, and finally view the masterpieces at Giudecca 795 Art Gallery.

To see traveler tips, other places to visit, maps, and tourist information, you can read our Venice itinerary planner .

You can take a train from Florence to Venice in 2.5 hours. Other options are to drive; or take a bus. In June, daily temperatures in Venice can reach 81°F, while at night they dip to 63°F. Finish up your sightseeing early on the 19th (Fri) so you can go by car to Siena.

Things to do in Venice

Historic Sites Museums Shopping
Highlights from your plan
Piazza San Marco ©
Piazza San Marco
Doge's Palace ©
Doge's Palace
Canal Grande ©
Canal Grande

3
nights
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Start off your visit on the 20th (Sat): take in the spiritual surroundings of Abbazia di San Galgano, pause for some serene contemplation at Duomo di Siena, and then steep yourself in history at Centro Storico di Siena. Get ready for a full day of sightseeing on the 21st (Sun): admire the verdant scenery at Val d'Orcia, then take a stroll around San Quirico d'Orcia, and then make a trip to Piazza del Campo.

For photos, ratings, maps, and other tourist information, refer to the Siena attractions planner.

Drive from Venice to Siena in 3.5 hours. Alternatively, you can take a train; or take a bus. June in Siena sees daily highs of 84°F and lows of 61°F at night. On the 22nd (Mon), wrap the sightseeing up by early afternoon so you can drive to Verona.

Things to do in Siena

Historic Sites Shopping Nature

Side Trips

Abbazia di San Galgano, Val d'Orcia, San Quirico d'Orcia
Highlights from your plan
Val d'Orcia ©
Val d'Orcia
Duomo di Siena ©
Duomo di Siena
Piazza del Campo ©
Piazza del Campo

3
nights
Verona

Verona ©
The famous setting for Shakespeare's star-crossed lovers, Romeo and Juliet, Verona is one of northern Italy's main tourist destinations, largely owing to its incredibly rich artistic heritage.
Take a break from the city and head to Parco Naturalistico delle Cascate-Family and Spiaggia Castelletto di Brenzone. Attractions like Arena di Verona and Museo di Castelvecchio make great kid-friendly stops. Step out of Verona to go to Garda and see Lago di Garda, which is approximately 1h 20 min away. The adventure continues: hunt for treasures at Piazza delle Erbe, admire the landmark architecture of Casa di Giulietta, take in the architecture and atmosphere at Chiesa di San Procolo, and take a tour by water with Boat Tours & Water Sports.

For reviews, traveler tips, other places to visit, and other tourist information, refer to the Verona attractions planner.

You can drive from Siena to Verona in 3.5 hours. Alternatively, you can do a combination of bus and train; or take a train. In June, plan for daily highs up to 84°F, and evening lows to 63°F. Wrap up your sightseeing by early afternoon on the 25th (Thu) to allow enough time to travel back home.

Things to do in Verona

Parks Nature Outdoors

Side Trips

Spiaggia Castelletto di Brenzone, Lago di Garda
Highlights from your plan
Piazza delle Erbe ©
Piazza delle Erbe
Arena di Verona ©
Arena di Verona
Museo di Castelvecchio ©
Museo di Castelvecchio

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