19 days in Italy Itinerary

19 days in Italy Itinerary

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Route & dates

19 days in Italy Itinerary

Start: Toronto
Fly:  12​h 30​min
1
Rome
— 1 night
Train:  2​h
2
Florence
— 1 night
Bus:  1​h 15​min
3
Siena
— 1 night
Bus:  1​h 15​min
4
Florence
— 1 night
Train:  1​h
5
Pisa
— Few hours
Train:  1​h 45​min
6
Cinque Terre
— Few hours
Drive:  2​h 30​min
7
Florence
— 2 nights
Train:  1​h 45​min
8
Milan
— 1 night
Train:  2​h 30​min
9
Venice
— 1 night
train:  1​h 30​min
10
Verona
— 1 day
Bus:  1​h 30​min
11
Venice
— 2 nights
train:  6​h
12
Sorrento
— 1 night
Subway:  45​min
13
Pompeii
— Few hours
Subway:  45​min
14
Sorrento
— 1 night
Ferry:  1​h
15
Amalfi
— Few hours
Drive:  3​h 15​min
16
Capri, Island of Capri
— Few hours
Drive:  3​h
17
Sorrento
— 1 night
Subway + Train:  2​h 45​min
18
Rome
— Few hours
Subway:  15​min
19
Vatican City
— 1 night
Subway:  15​min
20
Rome
— 3 nights
Fly:  12​h 30​min
End: Toronto

1
night
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Your day-by-day itinerary now includes Pantheon, Trevi Fountain and Spanish Steps. On the 7th (Sat), admire the local landmark of Trevi Fountain, then don't miss a visit to Spanish Steps, and then pause for some serene contemplation at Pantheon.

To find more things to do, reviews, maps, and other tourist information, you can read our Rome tour itinerary builder tool .

Toronto, Canada to Rome is an approximately 13-hour flight. You can also do a combination of ferry and flight; or do a combination of shuttle and flight. The time zone difference moving from Eastern Standard Time to Central European Time is 6 hours. While traveling from Toronto, expect a bit warmer days and about the same nights in Rome, ranging from highs of 32°C to lows of 18°C. On the 8th (Sun), you'll travel to Florence.

Things to do in Rome

Historic Sites
Find places to stay Sep 7 — 8:
Highlights from your plan
Pantheon ©
Pantheon
Trevi Fountain ©
Trevi Fountain
Spanish Steps ©
Spanish Steps

1
night
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 8th (Sun): take in nature's colorful creations at Giardino Torrigiani, pause for some serene contemplation at Chiesa di San Michele a Monteripaldi, take some stellar pictures from Basilica San Miniato al Monte, see the interesting displays at Certosa del Galluzzo, then step into the grandiose world of Castello di Montefioralle, and finally take in the spiritual surroundings of Chiesa Di Santo Stefano A Montefioralle.

To see topicsMoreInfo.option.ratings, where to stay, reviews, and other tourist information, refer to the Florence holiday builder site .

Take a train from Rome to Florence in 2 hours. Alternatively, you can drive; or fly. In September in Florence, expect temperatures between 30°C during the day and 17°C at night. Finish up your sightseeing early on the 9th (Mon) so you can catch the bus to Siena.

Things to do in Florence

Historic Sites Parks Museums

Side Trips

Greve in Chianti, Certosa del Galluzzo
Find places to stay Sep 8 — 9:
Highlights from your plan
Basilica San Miniato al Monte
Basilica San Miniato al Monte
Castello di Montefioralle ©
Castello di Montefioralle
Certosa del Galluzzo ©
Certosa del Galluzzo

1
night
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
On the 9th (Mon), learn about winemaking at Fattoria dei Barbi, do a tasting at Poggio Rubino, learn about winemaking at Winery Solaria Patrizia Cencioni, learn about winemaking at Azienda Agricola Capanna di Cencioni, then do a tasting at Il Palazzone, and finally do a tasting at Enoteca di Piazza Wine Room. Keep things going the next day: learn about winemaking at Casato Prime Donne and then learn about winemaking at Castiglion del Bosco.

To see topicsMoreInfo.option.ratings, reviews, maps, and tourist information, you can read our Siena trip planning tool .

Getting from Florence to Siena by bus takes about 1.5 hours. Other options: drive; or take a train. In September in Siena, expect temperatures between 32°C during the day and 19°C at night. Wrap up your sightseeing by early afternoon on the 10th (Tue) to allow enough time to take a bus to Florence.

Things to do in Siena

Wineries Historic Sites

Side Trip

Montalcino
Find places to stay Sep 9 — 10:
Highlights from your plan
Castiglion del Bosco ©
Castiglion del Bosco
Winery Solaria Patrizia Cencioni ©
Poggio Rubino ©
Poggio Rubino

1
night
Florence

Florence ©
Start off your visit on the 10th (Tue): look for gifts at Libreria Castalia SAS.

For more things to do, where to stay, topicsMoreInfo.option.ratings, and more tourist information, read our Florence travel tool .

Traveling by bus from Siena to Florence takes 1.5 hours. Alternatively, you can drive; or take a train. On the 11th (Wed), wrap the sightseeing up by early afternoon so you can take a train to Pisa.

Things to do in Florence

Wineries Shopping Historic Sites

Side Trip

Azienda Agricola Il Palagio di Panzano
Find places to stay Sep 10 — 11:
Highlights from your plan
Azienda Agricola Il Palagio di Panzano ©
Cimitero Evangelico Agli Allori ©
Cimitero Evangelico Agli Allori

few
hours
Pisa

Pisa
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
To see traveler tips, maps, topicsMoreInfo.option.ratings, and tourist information, read our Pisa trip planner.

Getting from Florence to Pisa by train takes about an hour. Other options: take a bus; or drive. Expect a daytime high around 30°C in September, and nighttime lows around 17°C. You will leave for Cinque Terre on the 11th (Wed).

Things to do in Pisa

Outdoors Tours Historic Sites
Find places to stay Sep 11 — 12:

few
hours
Cinque Terre

Cinque Terre ©
Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Kick off your visit on the 11th (Wed): take in the architecture and atmosphere at Santa Margherita di Antiochia Church.

To find reviews, traveler tips, other places to visit, and other tourist information, use the Cinque Terre travel planner.

Traveling by train from Pisa to Cinque Terre takes 2 hours. Alternatively, you can drive; or take a bus. In September in Cinque Terre, expect temperatures between 30°C during the day and 17°C at night. Wrap up your sightseeing on the 11th (Wed) early enough to drive to Florence.

Things to do in Cinque Terre

Historic Sites
Find places to stay Sep 11 — 12:
Highlights from your plan
Santa Margherita di Antiochia Church ©

2
nights
Florence

Florence ©
On the 12th (Thu), explore the world behind art at Pitti Palace, explore the historical opulence of Castello di Verrazzano, then learn about winemaking at Enoteca Falorni, and finally step into the grandiose world of Castello dei Conti Guidi di Poppi.

To see topicsMoreInfo.option.ratings, reviews, maps, and tourist information, read Florence route builder website .

Traveling by car from Cinque Terre to Florence takes 2.5 hours. Alternatively, you can take a train. Finish your sightseeing early on the 13th (Fri) to allow enough time to take a train to Milan.

Things to do in Florence

Wineries Historic Sites Museums

Side Trips

Greve in Chianti, Castello dei Conti Guidi di Poppi
Find places to stay Sep 11 — 13:
Highlights from your plan
Pitti Palace ©
Pitti Palace
Castello dei Conti Guidi di Poppi ©
Castello dei Conti Guidi di Poppi
Castello di Verrazzano ©
Castello di Verrazzano

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.
Your day-by-day itinerary now includes Leonardo's Last Supper Tickets as well as Duomo di Milano. Kick off your visit on the 13th (Fri): do sightseeing your way with Leonardo's Last Supper Tickets, contemplate in the serene atmosphere at Duomo di Milano, identify plant and animal life at Bosco Grande, pause for some serene contemplation at Chiesa di San Lanfranco, then pause for some serene contemplation at Chiesa di San Francesco, and finally take in the architecture and atmosphere at Santa Maria di Canepanova.

To find reviews, where to stay, other places to visit, and more tourist information, go to the Milan road trip site .

You can take a train from Florence to Milan in 2 hours. Other options are to drive; or fly. Expect a daytime high around 28°C in September, and nighttime lows around 16°C. Finish up your sightseeing early on the 14th (Sat) so you can catch the train to Venice.

Things to do in Milan

Historic Sites Wildlife Parks

Side Trip

Pavia
Find places to stay Sep 13 — 14:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Basilica San Michele Maggiore ©
Basilica San Michele Maggiore
Chiesa di San Salvatore (San Mauro) ©

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.
Your day-by-day itinerary now includes Gondolas4all as well as Canal Grande. Kick off your visit on the 14th (Sat): take a tour by water with Gondolas4all, contemplate the waterfront views at Canal Grande, and then take in the architecture and atmosphere at Parrocchia San Nicolo.

For traveler tips, reviews, photos, and more tourist information, you can read our Venice visit planner.

Getting from Milan to Venice by train takes about 2.5 hours. Other options: drive; or do a combination of flight and train. In September, plan for daily highs up to 29°C, and evening lows to 17°C. Cap off your sightseeing on the 15th (Sun) early enough to catch the bus to Verona.

Things to do in Venice

Nature Parks Outdoors

Side Trip

Parrocchia San Nicolo
Find places to stay Sep 14 — 15:
Highlights from your plan
Canal Grande ©
Canal Grande
Gondolas4all ©
Gondolas4all

1
day
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.
Your day-by-day itinerary now includes Free Walking Tour Verona, Museo di Castelvecchio and Palazzo Giardino Giusti. Kick off your visit on the 15th (Sun): enjoy breathtaking views from Torre Pentagona, then catch all the local highlights with Free Walking Tour Verona, then contemplate the long history of Museo di Castelvecchio, and finally admire the natural beauty at Palazzo Giardino Giusti.

To find traveler tips, maps, more things to do, and other tourist information, you can read our Verona trip itinerary planning website .

Traveling by bus from Venice to Verona takes 1.5 hours. Alternatively, you can drive; or take a shuttle. September in Verona sees daily highs of 30°C and lows of 17°C at night. Finish your sightseeing early on the 15th (Sun) to allow enough time to take a bus to Venice.

Things to do in Verona

Tours Historic Sites Parks
Find places to stay Sep 15 — 16:
Highlights from your plan
Free Walking Tour Verona ©
Free Walking Tour Verona
Museo di Castelvecchio ©
Museo di Castelvecchio
Palazzo Giardino Giusti ©
Palazzo Giardino Giusti

2
nights
Venice

Venice ©
To see maps, reviews, where to stay, and more tourist information, refer to the Venice trip planning website .

You can take a bus from Verona to Venice in 1.5 hours. Alternatively, you can drive; or take a shuttle. On the 17th (Tue), you're off to Sorrento.

Things to do in Venice

Museums Nature Wildlife

Side Trips

Parco Naturale Regionale del Delta del Po, Museo Archeologico Nazionale di Adria, Villa Duodo, Balbi Valier, Museo della Navigazione Fluviale di Battaglia Terme, Museo Nazionale Atestino
Find places to stay Sep 15 — 17:
Highlights from your plan

1
night
Sorrento

Sorrento ©
A lovely town easily accessible from almost anywhere in the country, Sorrento overlooks the Bay of Naples and sits right on the Amalfi Drive.
Kick off your visit on the 17th (Tue): take in the spiritual surroundings of St Francis Church and Convent, pause for some serene contemplation at Duomo dei San Filippo e Giacomo, and then take in the spiritual surroundings of Basilica di Sant'Antonino.

To see maps, where to stay, photos, and more tourist information, go to the Sorrento online travel route planner .

Getting from Venice to Sorrento by combination of flight and subway takes about 5.5 hours. Other options: do a combination of flight, train, and subway; or drive. Traveling from Venice in September, Sorrento is a bit warmer at night with lows of 23°C. Cap off your sightseeing on the 18th (Wed) early enough to take the subway to Pompeii.

Things to do in Sorrento

Historic Sites
Find places to stay Sep 17 — 18:
Highlights from your plan
Basilica di Sant'Antonino ©
Basilica di Sant'Antonino
St Francis Church and Convent ©
St Francis Church and Convent

few
hours
Pompeii

Pompeii ©
Pompeii has been a tourist destination for more than 250 years.
Start off your visit on the 18th (Wed): explore the ancient world of Tempio d'Iside, explore the ancient world of House of Menander (Casa del Menandro), then delve into the distant past at Fullonica di Stephanus, then explore the ancient world of Forum, and finally admire the landmark architecture of Villa dei Misteri.

For photos, other places to visit, and more tourist information, use the Pompeii journey planner.

You can take a subway from Sorrento to Pompeii in an hour. Alternatively, you can drive; or take a bus. In September, daily temperatures in Pompeii can reach 31°C, while at night they dip to 20°C. On the 18th (Wed), wrap the sightseeing up by early afternoon so you can take a subway to Sorrento.

Things to do in Pompeii

Historic Sites
Find places to stay Sep 18 — 19:
Highlights from your plan
Tempio d'Iside ©
Tempio d'Iside
Forum ©
Forum
Villa dei Misteri ©
Villa dei Misteri

1
night
Sorrento

Sorrento ©
On the 18th (Wed), admire the natural beauty at Villa Comunale, do a tasting at Limonoro, then stop by Antonella Ferrante, and finally pause for some serene contemplation at Cattedrale di Sorrento.

For where to stay, other places to visit, topicsMoreInfo.option.ratings, and tourist information, read our Sorrento trip planner.

You can take a subway from Pompeii to Sorrento in an hour. Other options are to drive; or take a bus. Finish your sightseeing early on the 19th (Thu) to allow enough time to ride a ferry to Amalfi.

Things to do in Sorrento

Parks Wineries Historic Sites
Find places to stay Sep 18 — 19:
Highlights from your plan
Villa Comunale ©
Villa Comunale
Limonoro ©
Limonoro
Cattedrale di Sorrento ©
Cattedrale di Sorrento

few
hours
Amalfi

Amalfi ©
Known for its impressive hillside cascade of colorful stone buildings down to the Mediterranean shore, Amalfi is the cultural and commercial heart of southern Italy's Amalfi Coast.
Kick off your visit on the 19th (Thu): take in the spiritual surroundings of Luna Convento, then sample the fine beverages at Antichi Sapori d'Amalfi, and then contemplate in the serene atmosphere at Duomo di Sant'Andrea.

For more things to do, where to stay, maps, and other tourist information, refer to the Amalfi trip maker tool .

You can ride a ferry from Sorrento to Amalfi in an hour. Other options are to drive; or take a bus. In September, daytime highs in Amalfi are 30°C, while nighttime lows are 24°C. Wrap up your sightseeing by early afternoon on the 19th (Thu) to allow time for the car ride to Capri.

Things to do in Amalfi

Historic Sites Breweries & Distilleries Shopping
Find places to stay Sep 19 — 20:
Highlights from your plan
Duomo di Sant'Andrea ©
Duomo di Sant'Andrea
Antichi Sapori d'Amalfi ©
Antichi Sapori d'Amalfi

few
hours
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.
On the 19th (Thu), identify plant and animal life at Parco Astarita, get engrossed in the history at Villa San Michele, and then enjoy the sea views from Punta Carena Lighthouse.

To find topicsMoreInfo.option.ratings, other places to visit, reviews, and more tourist information, go to the Capri day trip app .

You can drive from Amalfi to Capri in 3.5 hours. Expect a daytime high around 31°C in September, and nighttime lows around 23°C. Finish up your sightseeing early on the 19th (Thu) so you can go by car to Sorrento.

Things to do in Capri

Historic Sites Museums Wildlife

Side Trip

Anacapri
Find places to stay Sep 19 — 20:
Highlights from your plan
Villa San Michele ©
Villa San Michele
Punta Carena Lighthouse ©
Punta Carena Lighthouse
Parco Astarita ©
Parco Astarita

1
night
Sorrento

Sorrento ©
Start off your visit on the 20th (Fri): don't miss a visit to Piazza Tasso and then contemplate in the serene atmosphere at Monastero di San Paolo.

For other places to visit, reviews, and other tourist information, you can read our Sorrento day trip planning website .

Drive from Capri to Sorrento in 3 hours. On the 20th (Fri), you'll have the morning to explore before heading off to Rome.

Things to do in Sorrento

Historic Sites

Side Trip

Monastero di San Paolo
Find places to stay Sep 19 — 20:
Highlights from your plan
Monastero di San Paolo ©
Monastero di San Paolo

few
hours
Rome

Rome ©
Start off your visit on the 20th (Fri): pause for some serene contemplation at Abbey of St. Paul Outside the Walls and then tour the pleasant surroundings at V Lounge Beach Club.

For reviews, topicsMoreInfo.option.ratings, traveler tips, and other tourist information, use the Rome trip planner.

Do a combination of subway and train from Sorrento to Rome in 3 hours. Alternatively, you can drive; or take a bus. Expect little chillier evenings in Rome when traveling from Sorrento in September, with lows around 18°C. Wrap up your sightseeing on the 20th (Fri) early enough to take a subway to Vatican City.

Things to do in Rome

Outdoors Beaches Parks
Find places to stay Sep 20 — 21:
Highlights from your plan
Abbey of St. Paul Outside the Walls ©
V Lounge Beach Club ©
V Lounge Beach Club

1
night
Vatican City

Vatican City ©
Covering 44 hectares (110 acres) in the city center of Rome, the wall-enclosed sovereign state of Vatican City is one of the most famous religious sites worldwide, serving as the papal residence and home of the Roman Catholic church.
Your day-by-day itinerary now includes Sistine Chapel.

To see other places to visit, traveler tips, reviews, and more tourist information, read our Vatican City road trip planner.

Vatican City is just a short distance from Rome. Expect a daytime high around 32°C in September, and nighttime lows around 18°C. Finish your sightseeing early on the 21st (Sat) to allow enough time to take a subway to Rome.

Things to do in Vatican City

Historic Sites Museums
Find places to stay Sep 20 — 21:
Highlights from your plan
Cupola di San Pietro ©
Cupola di San Pietro
St. Peter's Basilica ©
St. Peter's Basilica
Sistine Chapel ©
Sistine Chapel

3
nights
Rome

Rome ©
Your day-by-day itinerary now includes Colosseum. Kick off your visit on the 22nd (Sun): delve into the distant past at Colosseum, take in the spiritual surroundings of Abbey of St. Paul Outside the Walls, take in the architecture and atmosphere at Basilica Papale San Paolo fuori le Mura, then take in the spiritual surroundings of Monastero Di S.Benedetto, then explore the world behind art at Tarsie Turri, and finally take in the architecture and atmosphere at Cattedrale di Santa Maria - sec. XI-XII. On the next day, stop by Il Castello di Avalon, kick back and relax at Mediterranea, enjoy breathtaking views from Tor Boacciana, then stroll around Parco Urbano Pineta di Castel Fusano, and finally have some family-friendly fun at Paintball Sport City.

For traveler tips, more things to do, maps, and more tourist information, you can read our Rome day trip planning website .

Rome is just a short distance from Vatican City. Finish your sightseeing early on the 24th (Tue) to allow enough time to travel back home.

Things to do in Rome

Historic Sites Outdoors Parks

Side Trips

Anagni, Monastero Di S.Benedetto, Kayaking & Canoeing, Il Castello di Avalon, Fontana Della Bella Flora
Find places to stay Sep 21 — 24:
Highlights from your plan
Colosseum ©
Colosseum
Abbey of St. Paul Outside the Walls ©

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