29 days in Italy Itinerary

29 days in Italy Itinerary

Created using Inspirock Italy route planner

Make it your trip
Fly
1
Milan
— 1 night
Drive
2
Venice
— 4 nights
Drive
3
Florence
— 4 nights
Drive
4
Siena
— 3 nights
Drive
5
Assisi
— 3 nights
Drive
6
Ravello
— 4 nights
Drive
7
Naples
— 4 nights
Train
8
Rome
— 5 nights
Fly

S M T W T F S
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11
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19
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23
24
25
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27
28
29
30
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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.
On the 31st (Sun), take in the architecture and atmosphere at Basilica San Lorenzo Maggiore and then get your bearings at Pinacoteca Ambrosiana. Get ready for a full day of sightseeing on the next day: get engrossed in the history at Basilica di Sant'Ambrogio, then contemplate the long history of Castello Sforzesco, then pause for some serene contemplation at Duomo di Milano, and finally admire the striking features of Galleria Vittorio Emanuele II.

For ratings, photos, maps, and other tourist information, go to the Milan trip maker tool.

Jeddah, Saudi Arabia to Milan is an approximately 9-hour flight. You can also drive; or do a combination of ferry and car. The time zone changes from Arabian Standard Time to Central European Standard Time, which is usually a -2 hour difference. Traveling from Jeddah in October, things will get cooler in Milan: highs are around 21°C and lows about 13°C. Wrap up your sightseeing on the 1st (Mon) early enough to drive to Venice.

Things to do in Milan

Historic Sites · Museums · Shopping

Venice

— 4 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.
Explore Venice's surroundings by going to Scrovegni Chapel (in Padua) and Verona (Museo di Castelvecchio, Basilica di San Zeno Maggiore, &more). And it doesn't end there: explore the activities along Canal Grande, admire the striking features of Basilica di San Marco, get to know the fascinating history of Piazza San Marco, and contemplate the long history of Ponte dei Sospiri.

Quickly create a custom-made itinerary for Venice using our trip planner.

Drive from Milan to Venice in 3 hours. Alternatively, you can take a train; or fly. In November, plan for daily highs up to 15°C, and evening lows to 7°C. Finish up your sightseeing early on the 5th (Fri) so you can go by car to Florence.

Things to do in Venice

Historic Sites · Museums · Tours · Parks

Side Trips

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.
Explore the numerous day-trip ideas around Florence: Podere Pellicciano - Agrisole (in San Miniato) and Pisa (Museo Aviotruppe Esercito Italiano & Leaning Tower of Pisa). There's lots more to do: admire the masterpieces at Florence Academy of Fine Arts, don't miss a visit to Piazzale Michelangelo, steep yourself in history at Basilica of Santa Croce, and admire the natural beauty at The Boboli Gardens.

For other places to visit, traveler tips, and other tourist information, read our Florence road trip planning app.

Getting from Venice to Florence by car takes about 3 hours. Other options: take a train; or take a bus. In November in Florence, expect temperatures between 19°C during the day and 9°C at night. Wrap up your sightseeing on the 9th (Tue) to allow time to drive to Siena.

Things to do in Florence

Historic Sites · Museums · Tours · Wineries

Side Trips

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.
Explore the numerous day-trip ideas around Siena: Winery Solaria Patrizia Cencioni (in Montalcino), Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate) and Buccelletti - Cantina (in Castiglion Fiorentino). Next up on the itinerary: indulge your senses at some of the top wineries in the area, take in the architecture and atmosphere at Duomo di Siena, contemplate the long history of Centro Storico di Siena, and get a sense of history and politics at Palazzo Pubblico and Museo Civico.

To see traveler tips, maps, where to stay, and other tourist information, you can read our Siena driving holiday planning tool.

Traveling by car from Florence to Siena takes 1.5 hours. Alternatively, you can take a bus; or take a train. In November, plan for daily highs up to 20°C, and evening lows to 10°C. Finish your sightseeing early on the 12th (Fri) to allow enough time to drive to Assisi.

Things to do in Siena

Wineries · Historic Sites · Tours · Museums

Side Trips

Assisi

— 3 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Venture out of the city with trips to Perugia (Museo-Laboratorio di Tessitura a Mano Giuditta Brozzetti & Studio Moretti Caselli), Vineria del Carmine (in La Bruna) and Montioni Frantoio e Cantina (in Montefalco). There's lots more to do: take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi, step into the grandiose world of Rocca Maggiore, contemplate in the serene atmosphere at Basilica di Santa Maria degli Angeli - Porziuncola, and see the interesting displays at Museo della Porziuncola.

You can plan Assisi trip in no time by asking Inspirock to help create your itinerary.

Drive from Siena to Assisi in 2 hours. Alternatively, you can take a bus; or take a train. While traveling from Siena, expect slightly colder days and about the same nights in Assisi, ranging from highs of 17°C to lows of 7°C. Wrap up your sightseeing on the 15th (Mon) to allow time to drive to Ravello.

Things to do in Assisi

Historic Sites · Wineries · Museums

Side Trips

Ravello

— 4 nights
Best known for its celebrated terraced gardens, Ravello is a hidden gem of Italy's Amalfi Coast.
Venture out of the city with trips to Positano (Food Tours, Il Sentiero Degli Dei, &more) and Parrocchia Di San Gennaro (in Praiano). There's much more to do: take in the spiritual surroundings of Duomo di Sant'Andrea, steep yourself in history at Duomo di Ravello, take in nature's colorful creations at Villa Cimbrone Gardens, and head outdoors with Amalfi Coast.

To find more things to do, reviews, other places to visit, and tourist information, refer to the Ravello day trip planning site.

Drive from Assisi to Ravello in 5 hours. Alternatively, you can do a combination of train and taxi; or take a bus. Expect a bit warmer temperatures when traveling from Assisi in November; daily highs in Ravello reach 21°C and lows reach 17°C. Wrap up your sightseeing on the 19th (Fri) early enough to drive to Naples.

Things to do in Ravello

Parks · Outdoors · Nature · Historic Sites

Side Trips

Naples

— 4 nights
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Explore the numerous day-trip ideas around Naples: Sorrento (Wine Tours & Tastings & Food Tours). There's much more to do: explore the ancient world of Pompeii Archaeological Park, take in the pleasant sights at Lungomare Caracciolo, stroll the grounds of Catacombe di San Gennaro, and take in the architecture and atmosphere at Duomo di Napoli.

To see traveler tips, reviews, maps, and more tourist information, use the Naples day trip planning tool.

Traveling by car from Ravello to Naples takes 1.5 hours. Alternatively, you can take a bus. Traveling from Ravello in November, Naples is little chillier at night with lows of 11°C. Cap off your sightseeing on the 23rd (Tue) early enough to catch the train to Rome.

Things to do in Naples

Tours · Historic Sites · Wineries · Museums

Side Trips

Rome

— 5 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, nightlife, and museums. Your plan includes some of its best attractions: delve into the distant past at Colosseum, make a trip to Piazza Navona, explore the world behind art at Galleria Borghese, and contemplate the long history of St. Peter's Basilica.

To find photos, maps, other places to visit, and more tourist information, read Rome route planning tool.

You can take a train from Naples to Rome in 2 hours. Alternatively, you can drive; or fly. In November, daytime highs in Rome are 20°C, while nighttime lows are 9°C. Wrap up your sightseeing by early afternoon on the 28th (Sun) to allow time for travel back home.

Things to do in Rome

Historic Sites · Museums · Tours · Neighborhoods

Side Trip

Italy travel guide

4.6
Landmarks · Ruins · Sacred & Religious Sites
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.