16 days in Italy Itinerary

16 days in Italy Itinerary

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Route & dates

16 days in Italy Itinerary

Start: New York City
Bus + Fly:  11 h 30 min
1
Venice
— 2 nights
Fly:  3 h 15 min
2
Rome
— 3 nights
Train + Subway:  3 h
3
Ravello
— 3 nights
Drive:  4 h 30 min
4
Assisi
— 2 nights
Drive:  2 h 15 min
5
Florence
— 2 nights
Train:  1 h 45 min
6
Milan
— 2 nights
Fly:  12 h 30 min
End: New York City

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.
Venice is known for historic sites, museums, and nature. Your plan includes some of its best attractions: contemplate the waterfront views at Canal Grande, get to know the fascinating history of Piazza San Marco, take in panoramic vistas at St Mark's Campanile, and steep yourself in history at Doge's Palace.

To find other places to visit, more things to do, photos, and tourist information, read Venice trip itinerary planning tool.

New York City, USA to Venice is an approximately 11.5-hour combination of bus and flight. You can also fly; or do a combination of train and flight. The time zone difference moving from Eastern Standard Time to Central European Time is 6 hours. Traveling from New York City in October, expect a bit cooler with lows of 51°F in Venice. Finish your sightseeing early on the 5th (Mon) so you can travel to Rome.

Things to do in Venice

Historic Sites Museums Parks
Find places to stay Oct 2 — 5:
Highlights from your plan
Canal Grande ©
Canal Grande
Basilica di San Marco
Basilica di San Marco
Doge's Palace ©
Doge's Palace

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, and museums. Your plan includes some of its best attractions: delve into the distant past at Colosseum, admire the landmark architecture of Pantheon, don't miss a visit to Roman Forum, and contemplate the long history of St. Peter's Basilica.

To find maps, photos, reviews, and more tourist information, read our Rome trip itinerary builder.

You can fly from Venice to Rome in 3.5 hours. Alternatively, you can take a train; or drive. Traveling from Venice in October, expect nights in Rome to be about the same, around 55°F, while days are somewhat warmer, around 73°F. Cap off your sightseeing on the 8th (Thu) early enough to travel to Ravello.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trip

Vatican City
Find places to stay Oct 5 — 8:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

3
nights
Ravello

Ravello ©
Best known for its celebrated terraced gardens, Ravello is a hidden gem of Italy's Amalfi Coast.
You'll find plenty of places to visit near Ravello: I Suoni degli Dei - Pelagos (in Praiano) and Positano (Fornillo & Boat Tours & Water Sports).

For maps, where to stay, traveler tips, and other tourist information, read Ravello online holiday planner.

Traveling by combination of train and subway from Rome to Ravello takes 3 hours. Alternatively, you can drive; or do a combination of train and bus. Expect somewhat warmer evenings in Ravello when traveling from Rome in October, with lows around 63°F. Wrap up your sightseeing on the 11th (Sun) to allow time to drive to Assisi.

Things to do in Ravello

Outdoors Historic Sites Parks

Side Trips

Amalfi, Praiano, Positano, Chiesa di San Pancrazio Martire, Liquorificio Mansi Carlo
Find places to stay Oct 8 — 11:
Highlights from your plan
Fornillo ©
Fornillo
Duomo di Ravello ©
Duomo di Ravello

2
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Kick off your visit on the 12th (Mon): examine the collection at Museo della Porziuncola, learn about winemaking at Tili Vini Societa Agricola, learn about winemaking at Bibenda Assisi, then appreciate the extensive heritage 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 walk around Mount Subasio. Here are some ideas for day two: learn about winemaking at Azienda Agraria Saio, get to know the fascinating history of Centro Storico di Assisi, explore the historical opulence of Rocca Maggiore, then take in the spiritual surroundings of Eremo delle Carceri, and finally take in the spiritual surroundings of San Damiano.

To see where to stay, other places to visit, photos, and more tourist information, refer to the Assisi trip planning app.

Traveling by car from Ravello to Assisi takes 4.5 hours. Alternatively, you can take a train; or do a combination of bus and train. Traveling from Ravello in October, you can expect nighttime temperatures to be a bit cooler in Assisi, with lows of 51°F. Finish your sightseeing early on the 13th (Tue) to allow enough time to drive to Florence.

Things to do in Assisi

Historic Sites Wineries Parks
Find places to stay Oct 11 — 13:
Highlights from your plan
Tili Vini Societa Agricola ©
Tili Vini Societa Agricola
Eremo delle Carceri ©
Eremo delle Carceri

2
nights
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 14th (Wed): snap pictures at Ponte Vecchio, don't miss a visit to Piazzale Michelangelo, then examine the collection at Pitti Palace, then contemplate the long history of Basilica of Santa Croce, and finally explore the world behind art at Academy Of Florence Art Gallery. Get ready for a full day of sightseeing on the 15th (Thu): ponder the world of politics at Palazzo Vecchio, contemplate in the serene atmosphere at The Baptistery of St. John, take in panoramic vistas at Campanile di Giotto, then pause for some serene contemplation at Cathedral of Santa Maria del Fiore, then appreciate the extensive heritage of Piazza del Duomo, and finally appreciate the extensive heritage of Piazza della Signoria.

To see ratings, photos, and other tourist information, use the Florence online vacation planner.

You can drive from Assisi to Florence in 2.5 hours. Alternatively, you can take a train. In October, daytime highs in Florence are 71°F, while nighttime lows are 54°F. Wrap up your sightseeing on the 15th (Thu) early enough to take a train to Milan.

Things to do in Florence

Historic Sites Museums
Find places to stay Oct 13 — 15:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

2
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.
Kick off your visit on the 16th (Fri): explore the world behind art at Pinacoteca Ambrosiana, then take in the architecture and atmosphere at Chiesa di San Maurizio al Monastero Maggiore, then take in the architecture and atmosphere at Duomo di Milano, and finally make a trip to Galleria Vittorio Emanuele II. On your second day here, get engrossed in the history at Museo Fratelli Cozzi Alfa Romeo and then steep yourself in history at Castello Sforzesco.

To find where to stay, reviews, ratings, and other tourist information, go to the Milan day trip planner.

You can take a train from Florence to Milan in 2 hours. Other options are to drive; or fly. Traveling from Florence in October, you will find days in Milan are slightly colder (65°F), and nights are about the same (52°F). Finish up your sightseeing early on the 17th (Sat) so you can travel back home.

Things to do in Milan

Historic Sites Museums Shopping

Side Trip

Museo Fratelli Cozzi Alfa Romeo
Find places to stay Oct 15 — 17:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Pinacoteca Ambrosiana ©
Pinacoteca Ambrosiana

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