23 days in Italy Itinerary

23 days in Italy Itinerary

Created using Inspirock Italy route builder
Make it your trip
Fly
1
Milan
— 1 night
Drive
2
Venice
— 3 nights
Drive
3
Florence
— 4 nights
Drive
4
Siena
— 3 nights
Drive
5
Assisi
— 1 night
Drive
6
Rome
— 4 nights
Train
7
Pompeii
— 2 nights
Drive
8
Amalfi
— 4 nights
Fly

S M T W T F S
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31
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5

Milan — 1 night

Fashion Capital of World

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 10th (Mon): take in the architecture and atmosphere at Basilica di Sant'Ambrogio, explore the world behind art at Pinacoteca Ambrosiana, then take in the architecture and atmosphere at Duomo di Milano, and finally buy something for everyone on your list at Galleria Vittorio Emanuele II.

To find more things to do, ratings, photos, and more tourist information, read our Milan online trip itinerary builder.

Chennai, India to Milan is an approximately 14.5-hour flight. You can also drive. The time zone difference when traveling from Chennai to Milan is minus 4.5 hours. Traveling from Chennai in October, things will get colder in Milan: highs are around 21°C and lows about 13°C. Finish your sightseeing early on the 10th (Mon) to allow enough time to drive to Venice.
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Museums · Historic Sites · Shopping
Find places to stay Oct 9 — 10:

Venice — 3 nights

City of Romance

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 still lots to do: contemplate the waterfront views at Canal Grande, take in the views from Ponte dei Sospiri, see the interesting displays at Doge's Palace, and explore the world behind art at Peggy Guggenheim Collection.

To find maps, where to stay, other places to visit, and more tourist information, read Venice holiday maker app.

Traveling by car from Milan to Venice takes 3 hours. Alternatively, you can take a train; or take a bus. In October, plan for daily highs up to 22°C, and evening lows to 12°C. Finish your sightseeing early on the 13th (Thu) to allow enough time to drive to Florence.
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Historic Sites · Tours · Museums · Parks
Side Trip
Find places to stay Oct 10 — 13:

Florence — 4 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Step out of Florence to go to Santa Brigida and see Castello del Trebbio, which is approximately 36 minutes away. There's much more to do: admire the masterpieces at Florence Academy of Fine Arts, make a trip to Piazzale Michelangelo, take in nature's colorful creations at The Boboli Gardens, and admire the striking features of The Baptistery of St. John.

To find photos, traveler tips, maps, and more tourist information, read our Florence itinerary app.

You can drive from Venice to Florence in 3 hours. Alternatively, you can take a train; or take a bus. In October, daily temperatures in Florence can reach 25°C, while at night they dip to 14°C. Wrap up your sightseeing on the 17th (Mon) early enough to drive to Siena.
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Historic Sites · Museums · Wineries · Tours
Side Trip
Find places to stay Oct 13 — 17:

Siena — 3 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Go for a jaunt from Siena to Castelnuovo dell'Abate to see Ciacci Piccolomini d'Aragona about 1h 5 min away. There's lots more to do: awaken your taste buds at some of the top wineries in the area, contemplate in the serene atmosphere at Battistero di San Giovanni, make a trip to Piazza del Campo, and pause for some serene contemplation at Duomo di Siena.

To see ratings, reviews, maps, and more tourist information, refer to the Siena online tour itinerary builder.

You can drive from Florence to Siena in 1.5 hours. Alternatively, you can take a bus; or take a train. October in Siena sees daily highs of 26°C and lows of 15°C at night. Wrap up your sightseeing on the 20th (Thu) to allow time to drive to Assisi.
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Tours · Wineries · Historic Sites
Side Trip
Find places to stay Oct 17 — 20:

Assisi — 1 night

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Kick off your visit on the 21st (Fri): examine the collection at Museo della Porziuncola, learn about winemaking at Tili Vini Societa Agricola, step into the grandiose world of Rocca Maggiore, then take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi, and finally do a tasting at Azienda Agraria Saio.

To find where to stay, maps, and other tourist information, use the Assisi day trip tool.

You can drive from Siena to Assisi in 2 hours. Other options are to take a bus; or take a train. Expect little chillier evenings in Assisi when traveling from Siena in October, with lows around 12°C. Wrap up your sightseeing on the 21st (Fri) early enough to drive to Rome.
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Wineries · Historic Sites · Museums
Find places to stay Oct 20 — 21:

Rome — 4 nights

Eternal City

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, sightseeing, and nightlife. Your trip includes some of its best attractions: admire the landmark architecture of Pantheon, contemplate the long history of St. Peter's Basilica, explore the ancient world of Palatine Hill, and admire the masterpieces at Galleria Borghese.

To see ratings, photos, traveler tips, and more tourist information, you can read our Rome trip maker.

Traveling by car from Assisi to Rome takes 2.5 hours. Alternatively, you can take a train; or take a bus. October in Rome sees daily highs of 26°C and lows of 15°C at night. Cap off your sightseeing on the 25th (Tue) early enough to catch the train to Pompeii.
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Historic Sites · Museums · Tours · Neighborhoods
Side Trip
Find places to stay Oct 21 — 25:

Pompeii — 2 nights

Underground City

Pompeii has been a tourist destination for more than 250 years.
Start off your visit on the 26th (Wed): contemplate the long history of Lupanar, delve into the distant past at Pompeii Archaeological Park, learn about winemaking at Bosco de Medici Winery, delve into the distant past at Forum, then admire the striking features of Villa dei Misteri, and finally delve into the distant past at House of Menander (Casa del Menandro). Keep things going the next day: make a trip to Promenade Trieste, take in the architecture and atmosphere at Duomo di Salerno, then admire the natural beauty at Giardino della Minerva, then explore the ancient world of Castello di Arechi, and finally take in the spiritual surroundings of Pontificio Santuario della Beata Maria Vergine del Santo Rosario di Pompei.

To see more things to do, maps, traveler tips, and tourist information, refer to the Pompeii trip planner.

Take a train from Rome to Pompeii in 2.5 hours. Alternatively, you can drive; or take a bus. In October in Pompeii, expect temperatures between 27°C during the day and 17°C at night. Finish your sightseeing early on the 27th (Thu) to allow enough time to drive to Amalfi.
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Historic Sites · Wineries · Parks
Side Trip
Find places to stay Oct 25 — 27:

Amalfi — 4 nights

Painted Town

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.
Change things up with these side-trips from Amalfi: Positano (Il Sentiero Degli Dei, Miniaci Art Gallery, &more). And it doesn't end there: steep yourself in history at Villa Rufolo, view the masterpieces at Ceramiche Cosmolena di Margherita di Palma, contemplate in the serene atmosphere at Cloister del Paradiso, and take in nature's colorful creations at Villa Cimbrone Gardens.

To see photos, maps, ratings, and more tourist information, read Amalfi holiday planning tool.

Getting from Pompeii to Amalfi by car takes about 1.5 hours. Other options: take a bus. In October, daily temperatures in Amalfi can reach 26°C, while at night they dip to 20°C. Wrap up your sightseeing on the 31st (Mon) to allow time to fly back home.
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Tours · Historic Sites · Outdoors · Museums
Side Trips
Find places to stay Oct 27 — 31:

Italy travel guide

4.6
Landmarks · Ruins · Beaches
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.
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