14 days in Italy Itinerary

14 days in Italy Itinerary

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Route & dates

14 days in Italy Itinerary

Start: Toronto
Fly:  11 h 30 min
1
Venice
— 1 night
Train:  2 h 30 min
2
Florence
— 2 nights
Drive:  2 h 30 min
3
Assisi
— 2 nights
Drive:  4 h 30 min
4
Ravello
— 3 nights
Drive:  3 h
5
Capri, Island of Capri
— 1 night
Ferry + Drive:  3 h 30 min
6
Rome
— 3 nights
Fly:  12 h 30 min
End: Toronto

1
night
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.
On the 16th (Mon), take in the views from Ponte di Rialto, explore the world behind art at Peggy Guggenheim Collection, then take in the architecture and atmosphere at Basilica di Sant’Antonio, then take in the spiritual surroundings of Scrovegni Chapel, and finally explore the activities along Canal Grande. On the 17th (Tue), you'll have a packed day of sightseeing: admire the landmark architecture of Basilica di San Marco, take in panoramic vistas at St Mark's Campanile, then snap pictures at Ponte dei Sospiri, then admire the striking features of Doge's Palace, and finally get to know the fascinating history of St. Mark's Square.

To find ratings, reviews, more things to do, and other tourist information, refer to the Venice trip itinerary maker app .

Toronto, Canada to Venice is an approximately 11.5-hour flight. You can also do a combination of flight and train. The time zone changes from Eastern Standard Time to Central European Time, which is usually a 6 hour difference. In September in Venice, expect temperatures between 29°C during the day and 17°C at night. Finish your sightseeing early on the 17th (Tue) so you can take a train to Florence.

Things to do in Venice

Historic Sites Museums Nature

Side Trip

Padua
Find places to stay Sep 16 — 17:
Highlights from your plan
Peggy Guggenheim Collection ©
Peggy Guggenheim Collection
Doge's Palace ©
Doge's Palace
Piazza San Marco ©
Piazza San Marco

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Start off your visit on the 18th (Wed): examine the collection at Academy Of Florence Art Gallery, admire the landmark architecture of Basilica San Miniato al Monte, then take some stellar pictures from Piazzale Michelangelo, then admire the masterpieces at Uffizi Galleries, and finally take in the views from Ponte Vecchio. On the 19th (Thu), you'll have a packed day of sightseeing: explore the world behind art at Chiesa e Museo di Orsanmichele, take an in-depth tour of Basilica di Santa Croce, explore the world behind art at Pitti Palace, then get to know the fascinating history of Piazza del Duomo, then contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, and finally contemplate the long history of The Baptistery of St. John.

To see traveler tips, reviews, other places to visit, and tourist information, refer to the Florence trip maker site .

Traveling by train from Venice to Florence takes 2.5 hours. Alternatively, you can drive; or take a bus. In September in Florence, expect temperatures between 30°C during the day and 17°C at night. Finish up your sightseeing early on the 19th (Thu) so you can go by car to Assisi.

Things to do in Florence

Museums Historic Sites
Find places to stay Sep 17 — 19:
Highlights from your plan
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore

2
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Start off your visit on the 20th (Fri): steep yourself in history at Basilica di Santa Chiara, take in the architecture and atmosphere at Basilica inferiore di San Francesco d'Assisi, appreciate the extensive heritage of Centro Storico, then pause for some serene contemplation at Basilica di Santa Maria degli Angeli - Porziuncola, then examine the collection at Museo della Porziuncola, and finally step into the grandiose world of Rocca Paolina. Get ready for a full day of sightseeing on the next day: contemplate in the serene atmosphere at Eremo delle Carceri, contemplate in the serene atmosphere at San Damiano, do a tasting at Tili Vini Societa Agricola, then take in the architecture and atmosphere at Cattedrale di Santa Maria Assunta Spoleto, and finally explore the historical opulence of Rocca Maggiore.

For photos, where to stay, and more tourist information, use the Assisi travel route tool .

Drive from Florence to Assisi in 2.5 hours. Alternatively, you can take a train. September in Assisi sees daily highs of 30°C and lows of 16°C at night. Wrap up your sightseeing on the 21st (Sat) to allow time to drive to Ravello.

Things to do in Assisi

Historic Sites Wineries Museums

Side Trips

Rocca Paolina, Cattedrale di Santa Maria Assunta Spoleto
Find places to stay Sep 19 — 21:
Highlights from your plan
Basilica di Santa Chiara ©
Basilica di Santa Chiara
Museo della Porziuncola ©
Museo della Porziuncola
San Damiano ©
San Damiano

3
nights
Ravello

Ravello ©
Get some cultural insight at Le Vigne di Raito and Villa Cimbrone Gardens. Duomo di Ravello and Villa Rufolo will appeal to history buffs. Change things up with a short trip to Fornillo in Positano (about 54 minutes away).

To see more things to do, photos, other places to visit, and other tourist information, read Ravello online trip itinerary maker .

You can drive from Assisi to Ravello in 4.5 hours. Other options are to take a train; or do a combination of train and bus. Expect a bit warmer evenings in Ravello when traveling from Assisi in September, with lows around 24°C. Finish up your sightseeing early on the 24th (Tue) so you can go by car to Capri.

Things to do in Ravello

Parks Beaches Outdoors

Side Trips

Le Vigne di Raito, Fornillo, Duomo di Sant'Andrea
Find places to stay Sep 21 — 24:
Highlights from your plan
Spiaggia di castiglione ©
Spiaggia di castiglione
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens
Duomo di Ravello ©
Duomo di Ravello

1
night
Capri, Island of Capri

Capri ©
The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
Kick off your visit on the 25th (Wed): get engrossed in the history at Villa San Michele, appreciate the extensive heritage of Scala Fenicia (Phoenician Steps), take in the spiritual surroundings of Santa Maria a Cetrella, then take in nature's colorful creations at Giardini di Augusto, then take in the dramatic natural features at I Faraglioni, and finally take in the spiritual surroundings of Chiesa San Michele.

To see other places to visit, where to stay, ratings, and other tourist information, read Capri driving holiday planner.

Getting from Ravello to Capri by car takes about 3 hours. In September, daytime highs in Capri are 31°C, while nighttime lows are 23°C. Finish your sightseeing early on the 25th (Wed) so you can travel to Rome.

Things to do in Capri

Historic Sites Museums Parks

Side Trip

Anacapri
Find places to stay Sep 24 — 25:
Highlights from your plan
Villa San Michele ©
Villa San Michele
I Faraglioni
I Faraglioni
Giardini di Augusto ©
Giardini di Augusto

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.
Palatine Hill and Vatican Museums will appeal to history buffs. Satisfy your inner culture vulture at Galleria Borghese and Colosseum. There's lots more to do: steep yourself in history at St. Peter's Basilica, admire the striking features of Pantheon, explore the ancient world of Foro di Augusto, and take a stroll through Trastevere.

For traveler tips, more things to do, ratings, and other tourist information, use the Rome vacation planning site .

Traveling by combination of ferry and car from Capri to Rome takes 3.5 hours. Alternatively, you can do a combination of ferry and train; or do a combination of ferry, subway, and train. Traveling from Capri in September, you can expect nighttime temperatures to be a bit cooler in Rome, with lows of 18°C. Wrap up your sightseeing on the 28th (Sat) to allow time to travel back home.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trip

Vatican City
Find places to stay Sep 25 — 28:
Highlights from your plan
St. Peter's Basilica ©
St. Peter's Basilica
Vatican Museums
Vatican Museums
Pantheon ©
Pantheon

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