21 days in Italy Itinerary

21 days in Italy Itinerary

Created using Inspirock Italy sightseeing planner

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Route & dates

21 days in Italy Itinerary

Start: Toronto
Fly:  11​h 15​min
1
Venice
— 3 nights
Fly:  3​h 15​min
2
Rome
— 3 nights
Train:  1​h 15​min
3
Naples
— 2 nights
Drive:  1​h 15​min
4
Ravello
— 4 nights
Drive:  4​h 30​min
5
Assisi
— 3 nights
Drive:  2​h 15​min
6
Florence
— 3 nights
Train:  1​h 45​min
7
Milan
— 1 night
Fly:  11​h 15​min
End: Toronto

3
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.
Explore Venice's surroundings by going to Verona (Basilica di San Zeno Maggiore, Arena di Verona, &more) and Scrovegni Chapel (in Padua). There's still lots to do: contemplate the waterfront views at Canal Grande, snap pictures at Ponte di Rialto, see the interesting displays at Doge's Palace, and capture your vacation like a pro with an inspiring photography tour.

To find more things to do, traveler tips, maps, and other tourist information, refer to the Venice travel route planner.

Toronto, Canada to Venice is an approximately 11.5-hour flight. You can also do a combination of ferry and flight; or 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. When traveling from Toronto in July, plan for somewhat warmer days in Venice, with highs around 36°C, while nights are about the same with lows around 22°C. Wrap up your sightseeing on the 5th (Sun) early enough to travel to Rome.

Things to do in Venice

Historic Sites Museums Tours

Side Trips

Verona, Scrovegni Chapel
Find places to stay Jul 1 — 5:
Highlights from your plan
Canal Grande ©
Canal Grande
Basilica di San Marco
Basilica di San Marco
Piazza San Marco ©
Piazza San Marco

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.
Rome is known for historic sites, nightlife, and museums. Your plan includes some of its best attractions: steep yourself in history at Colosseum, take a stroll through Trastevere, make a trip to Roman Forum, and take in the architecture and atmosphere at St. Peter's Basilica.

To see maps, other places to visit, more things to do, and other tourist information, use the Rome trip planner.

Fly from Venice to Rome in 3.5 hours. Alternatively, you can take a train; or drive. In July, plan for daily highs up to 37°C, and evening lows to 24°C. Finish your sightseeing early on the 8th (Wed) so you can take a train to Naples.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trip

St. Peter's Basilica
Find places to stay Jul 5 — 8:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
Trevi Fountain ©
Trevi Fountain

2
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Start off your visit on the 9th (Thu): appreciate the extensive heritage of Via Caracciolo e Lungomare di Napoli, then explore the galleries of Museo Cappella Sansevero, then contemplate the long history of Underground Naples, and finally examine the collection at Museo Archeologico Nazionale di Napoli. Get ready for a full day of sightseeing on the 10th (Fri): browse the exhibits of Galleria Borbonica, then make a trip to Via San Gregorio Armeno, and then take in nature's colorful creations at Reggia di Caserta.

To find topicsMoreInfo.option.ratings, traveler tips, reviews, and more tourist information, read our Naples tour builder website .

You can take a train from Rome to Naples in 1.5 hours. Alternatively, you can drive; or take a bus. In July, daytime highs in Naples are 36°C, while nighttime lows are 24°C. Cap off your sightseeing on the 10th (Fri) early enough to go by car to Ravello.

Things to do in Naples

Historic Sites Museums Parks

Side Trip

Reggia di Caserta
Find places to stay Jul 8 — 10:
Highlights from your plan
Galleria Borbonica ©
Galleria Borbonica
Museo Cappella Sansevero ©
Museo Cappella Sansevero

4
nights
Ravello

Ravello ©
Explore the numerous day-trip ideas around Ravello: Positano (Fornillo, Il Sentiero Degli Dei, &more).

To find traveler tips, topicsMoreInfo.option.ratings, reviews, and tourist information, you can read our Ravello online journey planner .

You can drive from Naples to Ravello in 1.5 hours. Other options are to do a combination of subway and taxi; or take a bus. Traveling from Naples in July, you can expect nighttime temperatures to be a bit warmer in Ravello, with lows of 29°C. Wrap up your sightseeing on the 14th (Tue) to allow time to drive to Assisi.

Things to do in Ravello

Outdoors Parks Beaches

Side Trips

Amalfi, Positano, Fondazione Lewitt - Villa Letizia
Find places to stay Jul 10 — 14:
Highlights from your plan
Fornillo ©
Fornillo
Speed Boats Tours

3
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Explore Assisi's surroundings by going to Grotte di Frasassi (in Genga) and Cascata delle Marmore (in Marmore). The adventure continues: pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, take in the spiritual surroundings of Basilica di Santa Maria degli Angeli - Porziuncola, examine the collection at Museo della Porziuncola, and admire the masterpieces at Museo-Laboratorio di Vetrate Artistiche Moretti Caselli.

To find maps, traveler tips, where to stay, and tourist information, you can read our Assisi trip itinerary builder tool .

Traveling by car from Ravello to Assisi takes 4.5 hours. Alternatively, you can take a train; or do a combination of bus and train. Plan for little chillier nights when traveling from Ravello in July since evenings lows in Assisi dip to 20°C. Wrap up your sightseeing on the 17th (Fri) early enough to drive to Florence.

Things to do in Assisi

Historic Sites Wineries Parks

Side Trips

Cascata delle Marmore, Grotte di Frasassi, Museo-Laboratorio di Vetrate Artistiche Moretti Caselli
Find places to stay Jul 14 — 17:
Highlights from your plan
Tili Vini Societa Agricola ©
Tili Vini Societa Agricola
Azienda Agraria Saio ©
Azienda Agraria Saio

3
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Explore Florence's surroundings by going to Siena (Piazza del Campo & Battistero di San Giovanni) and Leaning Tower of Pisa (in Pisa). And it doesn't end there: explore the world behind art at Academy Of Florence Art Gallery, make a trip to Piazzale Michelangelo, contemplate in the serene atmosphere at The Baptistery of St. John, and get engrossed in the history at Basilica di Santa Croce.

To see topicsMoreInfo.option.ratings, photos, traveler tips, and other tourist information, you can read our Florence journey planning app .

You can drive from Assisi to Florence in 2.5 hours. Alternatively, you can take a train. Expect a daytime high around 35°C in July, and nighttime lows around 21°C. Cap off your sightseeing on the 20th (Mon) early enough to catch the train to Milan.

Things to do in Florence

Historic Sites Museums Parks

Side Trips

Siena, Leaning Tower of Pisa
Find places to stay Jul 17 — 20:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

1
night
Milan

Milan ©
In many ways the most modern of Italian cities, Milan is a busy, elegant metropolis with an impressive list of grand palaces, fine churches, and important museums.
Kick off your visit on the 21st (Tue): admire the striking features of Galleria Vittorio Emanuele II, contemplate in the serene atmosphere at Duomo di Milano, then don't miss a visit to Piazza del Duomo, and finally contemplate the long history of Castello Sforzesco.

For traveler tips, where to stay, topicsMoreInfo.option.ratings, and more tourist information, use the Milan visit planning site .

Take a train from Florence to Milan in 2 hours. Alternatively, you can drive; or fly. July in Milan sees daily highs of 34°C and lows of 21°C at night. Cap off your sightseeing on the 21st (Tue) early enough to travel back home.

Things to do in Milan

Historic Sites Shopping
Find places to stay Jul 20 — 21:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Castello Sforzesco ©
Castello Sforzesco

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