19 days in Italy Itinerary

19 days in Italy Itinerary

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Route & dates

19 days in Italy Itinerary

Start: Windsor
Bus + Fly:  15​h 15​min
1
Milan
— 1 day
Train:  2​h 30​min
2
Venice
— 3 nights
Train:  2​h 15​min
3
Florence
— 3 nights
Drive:  2​h 15​min
4
Assisi
— 2 nights
Drive:  4​h 45​min
5
Positano
— 3 nights
Ferry:  1​h 30​min
6
Salerno
— 3 nights
Train:  1​h 45​min
7
Rome
— 3 nights
Fly + Bus:  12​h 30​min
End: Windsor

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 25th (Mon): admire the striking features of Galleria Vittorio Emanuele II and then take in the spiritual surroundings of Duomo di Milano.

For photos, maps, where to stay, and more tourist information, refer to the Milan planning tool .

Windsor, Canada to Milan is an approximately 15.5-hour combination of bus and flight. You can also fly; or do a combination of bus, car, and flight. You'll lose 6 hours traveling from Windsor to Milan due to the time zone difference. May in Milan sees daily highs of 26°C and lows of 15°C at night. Cap off your sightseeing on the 25th (Mon) early enough to catch the train to Venice.

Things to do in Milan

Historic Sites Shopping
Find places to stay May 25 — 26:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II

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.
Go for a jaunt from Venice to Padua to see Scrovegni Chapel about 54 minutes away. There's much more to do: explore the activities along Canal Grande, admire the landmark architecture of Basilica di San Marco, examine the collection at Doge's Palace, and admire the masterpieces at Gallerie dell'Accademia.

To see other places to visit, ratings, traveler tips, and more tourist information, refer to the Venice trip itinerary app .

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 26°C in May, and nighttime lows around 15°C. Cap off your sightseeing on the 28th (Thu) early enough to catch the train to Florence.

Things to do in Venice

Historic Sites Museums Nature

Side Trip

Scrovegni Chapel
Find places to stay May 25 — 28:
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.
Change things up with a short trip to Leaning Tower of Pisa in Pisa (about 1h 10 min away). Next up on the itinerary: explore the world behind art at Gallerie Degli Uffizi, see the interesting displays at Academy Of Florence Art Gallery, take in the views from Ponte Vecchio, and appreciate the extensive heritage of Piazza del Duomo.

To see where to stay, more things to do, and tourist information, you can read our Florence vacation planning site .

Traveling by train from Venice to Florence takes 2.5 hours. Alternatively, you can drive; or take a bus. In May, daytime highs in Florence are 25°C, while nighttime lows are 13°C. Finish your sightseeing early on the 31st (Sun) to allow enough time to drive to Assisi.

Things to do in Florence

Historic Sites Museums Parks

Side Trip

Leaning Tower of Pisa
Find places to stay May 28 — 31:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

2
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Kick off your visit on the 1st (Mon): get to know the fascinating history of Centro Storico, learn about winemaking at Bibenda Assisi, steep yourself in history at San Damiano, get to know the fascinating history of Piazza Superiore di San Francesco, then pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, and finally take in the spiritual surroundings of Cripta di San Francesco. On your second day here, take in the spiritual surroundings of Eremo delle Carceri, walk around Mount Subasio, do a tasting at Tili Vini Societa Agricola, do a tasting at Azienda Agraria Saio, then examine the collection at Museo della Porziuncola, and finally step into the grandiose world of Rocca Maggiore.

To see traveler tips, reviews, photos, and tourist information, refer to the Assisi trip itinerary planning website .

Traveling by car from Florence to Assisi takes 2.5 hours. Alternatively, you can take a train. In May, plan for daily highs up to 26°C, and evening lows to 13°C. Wrap up your sightseeing on the 2nd (Tue) to allow time to drive to Positano.

Things to do in Assisi

Historic Sites Wineries Museums
Find places to stay May 31 — Jun 2:
Highlights from your plan
Tili Vini Societa Agricola ©
Tili Vini Societa Agricola
Azienda Agraria Saio ©
Azienda Agraria Saio

3
nights
Positano

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.
Explore the numerous day-trip ideas around Positano: Parrocchia San Giovanni (in Vietri sul Mare), Amalfi (Wine Tours & Tastings, Museo della Carta, & more) and Ravello (Duomo di Ravello, Villa Rufolo, & more). There's still lots to do: take some stellar pictures from Il Sentiero Degli Dei, don't miss a visit to Fondazione Lewitt - Villa Letizia, head outdoors with I Suoni degli Dei - Pelagos, and enjoy the sand and surf at Fornillo.

To find more things to do, maps, and more tourist information, read our Positano trip itinerary planning tool .

You can drive from Assisi to Positano in 5 hours. Alternatively, you can do a combination of train and subway; or take a bus. Traveling from Assisi in June, Positano is a bit warmer at night with lows of 23°C. Wrap up your sightseeing on the 5th (Fri) early enough to ride a ferry to Salerno.

Things to do in Positano

Historic Sites Outdoors Parks

Side Trips

Ravello, Amalfi, Praiano, Parrocchia San Giovanni
Find places to stay Jun 2 — 5:
Highlights from your plan
Villa Rufolo ©
Villa Rufolo
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens

3
nights
Salerno

Salerno ©
While often overshadowed by the Amalfi Coast's array of quaint villages, Salerno has become one of the region's main areas for culture and entertainment, while remaining relatively unmarked by tourism.
Change things up with these side-trips from Salerno: Food Tours (in Sorrento) and Monte Finestra (in Tramonti). The adventure continues: delve into the distant past at Pompeii Archaeological Park, learn about winemaking at Le Vigne di Raito, get some thrills on the water with a speed boat tour, and get to know the fascinating history of Il Vecchio Centro Storico di Romagnano al Monte.

To see where to stay, traveler tips, and tourist information, refer to the Salerno online journey planner .

Traveling by ferry from Positano to Salerno takes 1.5 hours. Alternatively, you can do a combination of taxi and train; or drive. June in Salerno sees daily highs of 30°C and lows of 26°C at night. Finish up your sightseeing early on the 8th (Mon) so you can catch the train to Rome.

Things to do in Salerno

Tours Outdoors Transportation

Side Trips

Vietri sul Mare, Food Tours, Monte Finestra, Pompeii Archaeological Park
Find places to stay Jun 5 — 8:
Highlights from your plan
Le Vigne di Raito ©
Le Vigne di Raito
Speed Boats Tours
Monte Finestra ©
Monte Finestra

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, museums, classes, and shopping. Your plan includes some of its best attractions: explore the ancient world of Colosseum, steep yourself in history at Palatine Hill, admire the masterpieces at Galleria Borghese, and don't miss a visit to Spanish Steps.

To see reviews, more things to do, maps, and more tourist information, use the Rome tour builder app .

Traveling by train from Salerno to Rome takes 2 hours. Alternatively, you can drive; or take a bus. Traveling from Salerno in June, you can expect nighttime temperatures to be slightly colder in Rome, with lows of 21°C. Cap off your sightseeing on the 11th (Thu) early enough to travel back home.

Things to do in Rome

Historic Sites Museums

Side Trip

Vatican City
Find places to stay Jun 8 — 11:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
Trevi Fountain ©
Trevi Fountain

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