14 days in Italy Itinerary

14 days in Italy Itinerary

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Route & dates

14 days in Italy Itinerary

Start: Ponta Delgada, Sao Miguel
Fly:  10​h 30​min
1
Milan
— 1 night
train:  2​h 30​min
2
Venice
— 2 nights
Drive:  3​h 15​min
3
Pisa
— 2 nights
train:  1​h
4
Florence
— 2 nights
train:  1​h 45​min
5
Rome
— 3 nights
train:  1​h 15​min
6
Naples
— 2 nights
Fly:  10​h 15​min
End: Ponta Delgada, Sao Miguel

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.
On the 15th (Mon), admire the landmark architecture of Galleria Vittorio Emanuele II, then contemplate in the serene atmosphere at Duomo di Milano, then get to know the fascinating history of Piazza del Duomo, and finally step into the grandiose world of Castello Sforzesco.

For other places to visit, ratings, photos, and other tourist information, go to the Milan trip planner .

Ponta Delgada, Portugal to Milan is an approximately 10.5-hour flight. You can also do a combination of flight and train. Traveling from Ponta Delgada to Milan, you'll lose 2 hours due to the time zone difference. While traveling from Ponta Delgada, expect somewhat warmer days and about the same nights in Milan, ranging from highs of 33°C to lows of 20°C. Wrap up your sightseeing on the 15th (Mon) to allow time to take a train to Venice.

Things to do in Milan

Historic Sites 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 16th (Tue): admire the landmark architecture of Doge's Palace, then take in the views from Ponte dei Sospiri, then admire the striking features of Basilica di San Marco, and finally contemplate the waterfront views at Canal Grande. Keep things going the next day: snap pictures at Ponte di Rialto, get to know the fascinating history of Piazza San Marco, and then steep yourself in history at St Mark's Campanile.

For photos, traveler tips, more things to do, and tourist information, go to the Venice online road trip planner .

Traveling by train from Milan to Venice takes 2.5 hours. Alternatively, you can drive; or do a combination of flight and train. In June, daily temperatures in Venice can reach 32°C, while at night they dip to 20°C. Finish your sightseeing early on the 17th (Wed) to allow enough time to drive to Pisa.

Things to do in Venice

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

2
nights
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.
Kick off your visit on the 18th (Thu): admire the landmark architecture of Duomo di Pisa, then contemplate the long history of Camposanto, then make a trip to Piazza dei Miracoli, and finally take in panoramic vistas at Leaning Tower of Pisa. On the 19th (Fri), you'll have a packed day of sightseeing: admire the striking features of St Martin Cathedral, enjoy breathtaking views from Torre Guinigi, make a trip to Piazza Anfiteatro, then steep yourself in history at Le mura di Lucca, then get to know the fascinating history of Knights’ Square, and finally take in the spiritual surroundings of Battistero.

To find out how to plan a trip to Pisa, use our trip itinerary maker.

Traveling by car from Venice to Pisa takes 3.5 hours. Alternatively, you can take a train; or fly. In June in Pisa, expect temperatures between 32°C during the day and 18°C at night. Finish your sightseeing early on the 19th (Fri) to allow enough time to take a train to Florence.

Things to do in Pisa

Historic Sites

Side Trip

Lucca
Highlights from your plan
Duomo di Pisa ©
Duomo di Pisa
Leaning Tower of Pisa ©
Leaning Tower of Pisa
Piazza dei Miracoli ©
Piazza dei Miracoli

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Start off your visit on the 20th (Sat): examine the collection at Academy Of Florence Art Gallery, make a trip to Piazzale Michelangelo, explore the world behind art at Gallerie Degli Uffizi, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, then get to know the fascinating history of Piazza del Duomo, and finally admire the striking features of Loggia dei Lanzi. Get ready for a full day of sightseeing on the next day: explore the world behind art at Pitti Palace, take in the views from Ponte Vecchio, then enjoy breathtaking views from Campanile di Giotto, then take an in-depth tour of Basilica di Santa Croce, and finally get to know the fascinating history of Piazza della Signoria.

To see where to stay, ratings, and more tourist information, read Florence trip itinerary planning tool .

Getting from Pisa to Florence by train takes about an hour. Other options: take a bus; or drive. In June, daytime highs in Florence are 33°C, while nighttime lows are 21°C. Finish your sightseeing early on the 21st (Sun) so you can take a train to Rome.

Things to do in Florence

Museums Historic Sites
Highlights from your plan
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

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: delve into the distant past at Colosseum, don't miss a visit to Spanish Steps, admire the striking features of Pantheon, and admire the masterpieces at Galleria Borghese.

For maps, where to stay, and more tourist information, read Rome trip itinerary maker .

Take a train from Florence to Rome in 2 hours. Alternatively, you can drive; or fly. Expect a daytime high around 34°C in June, and nighttime lows around 21°C. Wrap up your sightseeing on the 24th (Wed) to allow time to take a train to Naples.

Things to do in Rome

Historic Sites Museums

Side Trip

Vatican City
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. Kick off your visit on the 25th (Thu): explore the ancient world of Pompeii Archaeological Park, steep yourself in history at Underground Naples, and then see the interesting displays at Museo Archeologico Nazionale di Napoli. Get ready for a full day of sightseeing on the 26th (Fri): explore the world behind art at Museo Cappella Sansevero, then browse the exhibits of Galleria Borbonica, then get to know the fascinating history of Via Caracciolo e Lungomare di Napoli, and finally do a tasting at Le Vigne di Raito.

To see traveler tips, reviews, photos, and other tourist information, refer to the Naples trip itinerary maker app .

You can take a train from Rome to Naples in 1.5 hours. Other options are to drive; or take a bus. June in Naples sees daily highs of 32°C and lows of 22°C at night. Finish up your sightseeing early on the 26th (Fri) so you can travel back home.

Things to do in Naples

Historic Sites Museums Wineries

Side Trips

Pompeii Archaeological Park, Le Vigne di Raito
Highlights from your plan
Le Vigne di Raito ©
Le Vigne di Raito
Pompeii Archaeological Park ©
Pompeii Archaeological Park

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