22 days in Italy Itinerary

22 days in Italy Itinerary

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Route & dates

22 days in Italy Itinerary

Start: Calgary
Fly:  15​h
1
Milan
— 1 day
train:  2​h 30​min
2
Venice
— 2 nights
train:  2​h 15​min
3
Florence
— 3 nights
bus:  1​h 15​min
4
Siena
— 2 nights
Drive:  1​h 45​min
5
Assisi
— 2 nights
Drive:  4​h 30​min
6
Amalfi
— 3 nights
bus:  30​min
7
Positano
— 2 nights
bus:  1​h 30​min
8
Naples
— 2 nights
train:  1​h 15​min
9
Rome
— 2 nights
Fly:  15​h 15​min
End: Calgary


Learn more about your trip

1
day
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 29th (Wed): buy something for everyone on your list at Galleria Vittorio Emanuele II, then take in the spiritual surroundings of Duomo di Milano, then don't miss a visit to Piazza del Duomo, and finally explore the historical opulence of Castello Sforzesco.

To find more things to do, maps, and tourist information, use the Milan trip itinerary app .

Calgary, Canada to Milan is an approximately 15-hour flight. You can also do a combination of flight and train; or do a combination of bus and flight. The time zone changes from Mountain Standard Time (MST) to Central European Time (CET), which is usually an 8 hour difference. Traveling from Calgary in April, things will get a bit warmer in Milan: highs are around 22°C and lows about 9°C. Finish your sightseeing early on the 29th (Wed) to allow enough time to take a train to Florence.

Things to do in Milan

Historic Sites Museums Shopping
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Castello Sforzesco ©
Castello Sforzesco

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 30th (Thu): contemplate the waterfront views at Canal Grande, take in the architecture and atmosphere at Basilica di San Marco, then snap pictures at Ponte dei Sospiri, and finally admire the landmark architecture of Doge's Palace. Keep things going the next day: contemplate the long history of Basilica dei Santi Giovanni e Paolo (San Zanipolo), take in the views from Ponte di Rialto, then get to know the fascinating history of Piazza San Marco, and finally make a trip to Peggy Guggenheim Collection.

To see other places to visit, where to stay, traveler tips, and other tourist information, you can read our Venice itinerary tool .

Getting from Milan to Venice by train takes about 2.5 hours. Other options: drive; or do a combination of flight and train. Expect a daytime high around 21°C in April, and nighttime lows around 11°C. Cap off your sightseeing on the 1st (Fri) early enough to catch the train to Florence.

Things to do in Venice

Historic Sites Museums Parks
Highlights from your plan
Canal Grande ©
Canal Grande
Doge's Palace ©
Doge's Palace
Basilica di San Marco
Basilica di San Marco

3
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Take a break from Florence with a short trip to Leaning Tower of Pisa in Pisa, about 1h 10 min away. There's still lots to do: admire the masterpieces at Gallerie Degli Uffizi, take in the views from Ponte Vecchio, contemplate in the serene atmosphere at The Baptistery of St. John, and take an in-depth tour of Basilica di Santa Croce.

To find maps, ratings, photos, and other tourist information, you can read our Florence online day trip planner .

You can take a train from Venice to Florence in 2.5 hours. Alternatively, you can drive; or take a bus. In May, plan for daily highs up to 25°C, and evening lows to 13°C. Wrap up your sightseeing on the 4th (Mon) to allow time to take a bus to Siena.

Things to do in Florence

Museums Historic Sites Parks

Side Trip

Leaning Tower of Pisa
Highlights from your plan
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

2
nights
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 5th (Tue): make a trip to Piazza del Campo and then savor the flavors at Food & Drink. Here are some ideas for day two: contemplate the long history of Centro Storico di Siena, then take in the architecture and atmosphere at Duomo di Siena, then get lost in a book at Biblioteca Piccolomini, and finally enjoy breathtaking views from Torre del Mangia.

To see ratings, more things to do, reviews, and other tourist information, refer to the Siena road trip app .

Traveling by bus from Florence to Siena takes 1.5 hours. Alternatively, you can drive; or take a train. In May, daily temperatures in Siena can reach 27°C, while at night they dip to 13°C. Finish up your sightseeing early on the 6th (Wed) so you can go by car to Assisi.

Things to do in Siena

Historic Sites Tours
Highlights from your plan
Wine Tours & Tastings
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

2
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Start off your visit on the 7th (Thu): take in the spiritual surroundings of Cripta di San Francesco, pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, appreciate the extensive heritage of Piazza Superiore di San Francesco, learn about winemaking at Tili Vini Societa Agricola, then see the interesting displays at Museo della Porziuncola, and finally take in the spiritual surroundings of Basilica di Santa Maria degli Angeli - Porziuncola. On your second day here, stroll around Parco del Monte Subasio, take in the spiritual surroundings of San Damiano, step into the grandiose world of Rocca Maggiore, then take in the spiritual surroundings of Santuario di Rivotorto, and finally do a tasting at Montioni Frantoio e Cantina.

To see where to stay, traveler tips, other places to visit, and more tourist information, use the Assisi online day trip planner .

Drive from Siena to Assisi in 2 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 26°C in May, and nighttime lows around 13°C. Cap off your sightseeing on the 8th (Fri) early enough to go by car to Amalfi.

Things to do in Assisi

Historic Sites Wineries Parks

Side Trip

Montioni Frantoio e Cantina
Highlights from your plan
Museo della Porziuncola ©
Museo della Porziuncola
Eremo delle Carceri ©
Eremo delle Carceri

3
nights
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.
Amalfi is known for historic sites, museums, adventure, nature, and nightlife. Your plan includes some of its best attractions: indulge your senses at some of the top wineries in the area, see the interesting displays at Museo della Carta, take in the spiritual surroundings of Sanctuary of Our Lady of Sorrow (Sancturio Maria Santissima Addolorata), and contemplate the long history of Duomo di Ravello.

To see ratings, photos, reviews, and tourist information, read our Amalfi travel route builder tool .

Traveling by car from Assisi to Amalfi takes 4.5 hours. Alternatively, you can take a train; or do a combination of train and bus. Traveling from Assisi in May, expect a bit warmer with lows of 21°C in Amalfi. Finish your sightseeing early on the 12th (Tue) so you can take a bus to Positano.

Things to do in Amalfi

Tours Historic Sites Transportation

Side Trips

Ravello, Amalfi Coast
Highlights from your plan
Wine Tours & Tastings
Villa Rufolo ©
Villa Rufolo
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens

2
nights
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.
Kick off your visit on the 12th (Tue): don't miss a visit to Parrocchia Di San Gennaro, enjoy the sand and surf at Fornillo, and then take some stellar pictures from Il Sentiero Degli Dei. On the 13th (Wed), you'll have a packed day of sightseeing: enjoy breathtaking views from Torre di Grado, Head underground at Cave of Smeraldo, and then indulge your senses at some of the top wineries in the area.

For more things to do, reviews, where to stay, and more tourist information, refer to the Positano route site .

Positano is just a short distance from Amalfi. Traveling from Amalfi in May, expect a bit cooler with lows of 18°C in Positano. Finish up your sightseeing early on the 14th (Thu) so you can catcht the bus to Naples.

Things to do in Positano

Transportation Tours Parks

Side Trip

Praiano
Highlights from your plan
Wine Tours & Tastings
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei
Fornillo ©
Fornillo

2
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. On the 14th (Thu), delve into the distant past at Parco Acheologico di Ercolano, then make a trip to Via San Gregorio Armeno, then admire the masterpieces at Museo Cappella Sansevero, and finally contemplate the long history of Underground Naples. Get ready for a full day of sightseeing on the 15th (Fri): don't miss a visit to Pompeii Archaeological Park, then get engrossed in the history at Galleria Borbonica, and then see the interesting displays at Museo Archeologico Nazionale di Napoli.

To find more things to do, maps, reviews, and other tourist information, you can read our Naples online sightseeing planner .

Traveling by bus from Positano to Naples takes 1.5 hours. Alternatively, you can drive; or do a combination of bus and subway. In May in Naples, expect temperatures between 27°C during the day and 17°C at night. Wrap up your sightseeing on the 16th (Sat) to allow time to take a train to Rome.

Things to do in Naples

Historic Sites Museums

Side Trips

Parco Acheologico di Ercolano, Pompeii Archaeological Park
Highlights from your plan
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Museo Cappella Sansevero ©
Museo Cappella Sansevero

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.
Rome is known for historic sites, nightlife, museums, classes, and shopping. Your plan includes some of its best attractions: explore the ancient world of Colosseum, don't miss a visit to Spanish Steps, admire the masterpieces at Galleria Borghese, and contemplate in the serene atmosphere at Vatican Museums.

To see more things to do, ratings, where to stay, and tourist information, read our Rome trip builder site .

Traveling by train from Naples to Rome takes 1.5 hours. Alternatively, you can drive; or take a bus. May in Rome sees daily highs of 28°C and lows of 17°C at night. Cap off your sightseeing on the 18th (Mon) early enough to travel back home.

Things to do in Rome

Historic Sites Museums

Side Trip

Vatican City
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
Trevi Fountain ©
Trevi Fountain

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