20 days in Italy Itinerary

20 days in Italy Itinerary

Created using Inspirock Europe trip planner

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Route & dates

20 days in Italy Itinerary

Start: Winnipeg
Fly:  14​h 15​min
1
Venice
— 2 nights
Drive:  3​h 15​min
2
Varenna
— 1 night
train:  1​h 15​min
3
Milan
— 3 nights
4
Modena
— 1 night
train:  1​h 30​min
5
Florence
— 3 nights
Drive:  1​h 45​min
6
Pienza
— 3 nights
Drive:  2​h 15​min
7
Rome
— 2 nights
Drive:  4​h
8
Conca dei Marini
— 2 nights
Drive:  4​h
9
Rome
— 1 night
Fly:  15​h 30​min
End: Winnipeg

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.
Kick off your visit on the 3rd (Tue): pause for some serene contemplation at Basilica di San Marco, admire the landmark architecture of Doge's Palace, contemplate the waterfront views at Canal Grande, then wander the streets of Cannaregio, and finally take a stroll through Campo del Ghetto. Get ready for a full day of sightseeing on the next day: steep yourself in history at Scala Contarini del Bovolo, don't miss a visit to St. Mark's Square, then capture your vacation like a pro with an inspiring photography tour, and finally contemplate in the serene atmosphere at Basilica Santa Maria Gloriosa dei Frari.

For ratings, where to stay, reviews, and more tourist information, read our Venice day trip planning app .

Winnipeg, Canada to Venice is an approximately 14.5-hour flight. You can also do a combination of flight and train; or do a combination of flight and shuttle. The time zone changes from Central Standard Time (CST) to Central European Time (CET), which is usually a 7 hour difference. Prepare for a bit warmer weather when traveling from Winnipeg in September: high temperatures in Venice hover around 29°C and lows are around 17°C. Wrap up your sightseeing on the 5th (Thu) early enough to drive to Varenna.

Things to do in Venice

Historic Sites Tours Neighborhoods
Find places to stay Sep 3 — 5:
Highlights from your plan
Canal Grande ©
Canal Grande
Piazza San Marco ©
Piazza San Marco
Basilica di San Marco
Basilica di San Marco

1
night
Varenna

Varenna ©
Varenna is a comune (municipality) on Lake Como in the Province of Lecco in the Italian region Lombardy, located about 60km north of Milan and about 20km northwest of Lecco.Varenna was founded by local fishermen in 769, and was later allied of the commune of Milan. Start off your visit on the 5th (Thu): take in the architecture and atmosphere at Chiesa di San Giorgio, take in the architecture and atmosphere at S. Giovanni Battista, admire the landmark architecture of Villa Monastero, then take in nature's colorful creations at Il Giardino Botanico - Hotel Villa Cipressi, and finally tour the pleasant surroundings at Sentiero del Viandante. Get ready for a full day of sightseeing on the 6th (Fri): take in the exciting artwork at Paul DEMARIA - The Open Lake & Landscape Studio d’Arte and then go for a walk through Green Way dei Patriarchi.

To find more things to do, traveler tips, and tourist information, read our Varenna travel planning tool .

Traveling by car from Venice to Varenna takes 3.5 hours. Alternatively, you can take a train; or do a combination of train and flight. In September, plan for daily highs up to 28°C, and evening lows to 16°C. Finish your sightseeing early on the 6th (Fri) to allow enough time to take a train to Milan.

Things to do in Varenna

Parks Trails Outdoors
Find places to stay Sep 4 — 6:
Highlights from your plan
Villa Monastero ©
Villa Monastero
S. Giovanni Battista ©
S. Giovanni Battista

3
nights
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.
Start off your visit on the 6th (Fri): take in the spiritual surroundings of Duomo di Milano and then make a trip to Piazza del Duomo.

Inspirock's itinerary builder makes planning a Milan trip simple and quick.

Take a train from Varenna to Milan in 1.5 hours. Alternatively, you can drive. In September in Milan, expect temperatures between 28°C during the day and 16°C at night. On the 9th (Mon), you'll travel to Modena.

Things to do in Milan

Historic Sites
Find places to stay Sep 6 — 9:
Highlights from your plan
Piazza del Duomo ©
Piazza del Duomo

1
night
Modena

Modena ©
Deemed the Capital of Engines, Modena is the birthplace of Enzo Ferrari and the headquarters of Italian sports cars.
Kick off your visit on the 9th (Mon): examine the collection at Casa Museo Luciano Pavarotti, then examine the collection at Acetaia Giuseppe Giusti, and then take in the spiritual surroundings of Duomo di Modena.

To find other places to visit, more things to do, ratings, and other tourist information, use the Modena road trip planning tool .

You can take a train from Milan to Modena in 2 hours. Other options are to drive; or take a shuttle. In September, daily temperatures in Modena can reach 30°C, while at night they dip to 17°C. On the 10th (Tue), you'll have the morning to explore before heading off to Florence.

Things to do in Modena

Museums Historic Sites
Find places to stay Sep 9 — 10:
Highlights from your plan
Casa Museo Luciano Pavarotti ©
Casa Museo Luciano Pavarotti
Duomo di Modena ©
Duomo di Modena
Galleria Estense ©
Galleria Estense

3
nights
Florence

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Eschew the tourist crowds and head to Centro Storico and Basilica San Miniato al Monte. When in Florence, make a side trip to see Canyon Park in Bagni di Lucca, approximately 1h 25 min away. The adventure continues: explore the world behind art at Uffizi Galleries, see the interesting displays at Academy Of Florence Art Gallery, appreciate the history behind Perseus Statue, and steep yourself in history at Loggia dei Lanzi.

To see ratings, maps, traveler tips, and other tourist information, read Florence vacation tool .

You can take a train from Modena to Florence in 1.5 hours. Other options are to take a bus; or drive. In September, daytime highs in Florence are 30°C, while nighttime lows are 17°C. Wrap up your sightseeing on the 13th (Fri) to allow time to drive to Pienza.

Things to do in Florence

Tours Historic Sites Museums

Side Trip

Canyon Park
Find places to stay Sep 10 — 13:
Highlights from your plan
Food Tours
Centro Storico ©
Centro Storico
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi

3
nights
Pienza

Pienza ©
Pienza, a town and comune in the province of Siena, in the Val d'Orcia in Tuscany (central Italy), between the towns of Montepulciano and Montalcino, is the "touchstone of Renaissance urbanism."In 1996, UNESCO declared the town a World Heritage Site, and in 2004 the entire valley, the Val d'Orcia, was included on the list of UNESCO's World Cultural Landscapes.HistoryBefore the village was renamed to Pienza its name was Corsignano. Eschew the tourist crowds and head to Piazza Pio II and Pieve di Corsignano. And it doesn't end there: pause for some serene contemplation at Cappella della Madonna di Vitaleta, explore and take pictures at Podere Il Casale, get to know the fascinating history of Borgo Medioevale di Monticchiello, and contemplate the long history of Palazzo Piccolomini.

To see more things to do, traveler tips, other places to visit, and tourist information, go to the Pienza trip itinerary planning app .

Traveling by car from Florence to Pienza takes 2 hours. Alternatively, you can take a bus; or do a combination of train and bus. Expect a daytime high around 32°C in September, and nighttime lows around 19°C. On the 16th (Mon), wrap the sightseeing up by early afternoon so you can drive to Rome.

Things to do in Pienza

Historic Sites Parks Wildlife

Side Trip

Cappella della Madonna di Vitaleta
Find places to stay Sep 13 — 16:
Highlights from your plan
Cathedral ©
Cathedral
Piazza Pio II ©
Piazza Pio II
Riserva Naturale Lucciolabella ©
Riserva Naturale Lucciolabella

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.
Kick off your visit on the 16th (Mon): contemplate the long history of Colosseum.

To see reviews, traveler tips, ratings, and tourist information, go to the Rome trip planner .

You can drive from Pienza to Rome in 2.5 hours. Alternatively, you can take a train; or do a combination of bus and train. In September, daily temperatures in Rome can reach 32°C, while at night they dip to 18°C. Finish your sightseeing early on the 18th (Wed) so you can travel to Conca dei Marini.

Things to do in Rome

Historic Sites

Side Trip

Vatican City
Find places to stay Sep 16 — 18:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

2
nights
Conca dei Marini

Conca dei Marini ©
Conca dei Marini is a town and comune in the province of Salerno in the Campania region of south-western Italy. Step out of Conca dei Marini to go to Eboli and see Bau Bau Beach Village, which is approximately 1h 20 min away. And it doesn't end there: stroll through Lido Capo di Conca, stop by Piccadilly, take in the architecture and atmosphere at Chiesa di San Pancrazio Martire, and take in panoramic vistas at Torre del Capo di Conca.

To find more things to do, maps, reviews, and more tourist information, read our Conca dei Marini road trip app .

You can drive from Rome to Conca dei Marini in 3.5 hours. Traveling from Rome in September, Conca dei Marini is somewhat warmer at night with lows of 24°C. You'll set off for Rome on the 20th (Fri).

Things to do in Conca dei Marini

Parks Beaches Outdoors

Side Trip

Bau Bau Beach Village
Find places to stay Sep 17 — 20:
Highlights from your plan
Bau Bau Beach Village ©
Bau Bau Beach Village
Lido Capo di Conca ©
Lido Capo di Conca
Grotta dello Smeraldo ©
Grotta dello Smeraldo

1
night
Rome

Rome
Start off your visit on the 21st (Sat): admire the masterpieces at Vatican Museums and then get to know the fascinating history of Piazza Navona.

For where to stay, traveler tips, reviews, and more tourist information, you can read our Rome travel itinerary planner .

Traveling by car from Conca dei Marini to Rome takes 3.5 hours. Traveling from Conca dei Marini in September, expect little chillier with lows of 18°C in Rome. Finish your sightseeing early on the 21st (Sat) so you can travel back home.

Things to do in Rome

Historic Sites Museums

Side Trip

Vatican Museums
Find places to stay Sep 20 — 21:
Highlights from your plan
Vatican Museums
Vatican Museums
Piazza Navona ©
Piazza Navona

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