29 days in Italy Itinerary

29 days in Italy Itinerary

Created using Inspirock Italy tour itinerary builder

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

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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 8th (Wed), pause for some serene contemplation at Basilica San Lorenzo Maggiore and then explore the world behind art at Pinacoteca Ambrosiana. On the 9th (Thu), you'll have a packed day of sightseeing: take an in-depth tour of Basilica di Sant'Ambrogio, then explore the historical opulence of Castello Sforzesco, then contemplate in the serene atmosphere at Duomo di Milano, and finally admire the landmark architecture of Galleria Vittorio Emanuele II.

To find more things to do, other places to visit, where to stay, and more tourist information, read our Milan trip planner.

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 (AST) to Central European Standard Time (CET), which is usually a -2 hour difference. Traveling from Jeddah in September, expect Milan to be much colder, temps between 28°C and 16°C. Wrap up your sightseeing on the 9th (Thu) to allow time 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 the numerous day-trip ideas around Venice: Verona (Museo di Castelvecchio, Basilica di San Zeno Maggiore, &more) and Scrovegni Chapel (in Padua). There's much more to do: contemplate the waterfront views at Canal Grande, admire the masterpieces at Peggy Guggenheim Collection, contemplate the long history of Ponte dei Sospiri, and admire the landmark architecture of Basilica di San Marco.

To find maps, more things to do, and tourist information, go to the Venice trip builder app.

Drive from Milan to Venice in 3 hours. Alternatively, you can take a train; or fly. Expect a daytime high around 29°C in September, and nighttime lows around 17°C. Finish your sightseeing early on the 13th (Mon) to allow enough time to drive to Florence.

Things to do in Venice

Historic Sites · Museums · Tours · Nature

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.
Get out of town with these interesting Florence side-trips: Pisa (Museo Aviotruppe Esercito Italiano & Leaning Tower of Pisa) and Podere Pellicciano - Agrisole (in San Miniato). There's still lots to do: admire the masterpieces at Florence Academy of Fine Arts, don't miss a visit to Piazzale Michelangelo, snap pictures at Ponte Vecchio, and examine the collection at Pitti Palace.

For maps, where to stay, traveler tips, and more tourist information, read our Florence online trip maker.

Getting from Venice to Florence by car takes about 3 hours. Other options: take a train; or take a bus. In September, daily temperatures in Florence can reach 30°C, while at night they dip to 17°C. Cap off your sightseeing on the 17th (Fri) early enough to go by car 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 Siena's surroundings by going to Buccelletti - Cantina (in Castiglion Fiorentino), Winery Solaria Patrizia Cencioni (in Montalcino) and Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate). There's still lots to do: indulge your senses at some of the top wineries in the area, steep yourself in history at Centro Storico di Siena, don't miss a visit to Piazza del Campo, and admire the masterpieces at Palazzo Pubblico and Museo Civico.

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

You can drive from Florence to Siena in 1.5 hours. Other options are to take a bus; or take a train. In September, plan for daily highs up to 32°C, and evening lows to 19°C. Finish your sightseeing early on the 20th (Mon) 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.
Change things up with these side-trips from Assisi: Vineria del Carmine (in La Bruna), Perugia (Museo-Laboratorio di Tessitura a Mano Giuditta Brozzetti & Studio Moretti Caselli) and Montioni Frantoio e Cantina (in Montefalco). There's much more to do: take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi, take in the spiritual surroundings of Basilica di Santa Maria degli Angeli - Porziuncola, step into the grandiose world of Rocca Maggiore, and steep yourself in history at Eremo delle Carceri.

To see maps, where to stay, photos, and other tourist information, refer to the Assisi trip itinerary builder app.

You can drive from Siena to Assisi in 2 hours. Other options are to take a bus; or take a train. In September, plan for daily highs up to 30°C, and evening lows to 16°C. Finish your sightseeing early on the 23rd (Thu) so you can 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.
You'll find plenty of places to visit near Ravello: Parrocchia Di San Gennaro (in Praiano) and Positano (Food Tours, Il Sentiero Degli Dei, &more). There's lots more to do: contemplate in the serene atmosphere at Duomo di Sant'Andrea, admire the landmark architecture of Villa Rufolo, admire the natural beauty at Villa Cimbrone Gardens, and steep yourself in history at Duomo di Ravello.

To see photos, other places to visit, where to stay, and tourist information, refer to the Ravello online road trip planner.

Traveling by car from Assisi to Ravello takes 5 hours. Alternatively, you can do a combination of train and taxi; or take a bus. Traveling from Assisi in September, Ravello is a bit warmer at night with lows of 24°C. Finish your sightseeing early on the 27th (Mon) to allow enough time 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 Naples' surroundings by going to Sorrento (Wine Tours & Tastings & Food Tours). There's much more to do: contemplate the long history of Pompeii Archaeological Park, delve into the distant past at Teatro Grande, explore the different monuments and memorials at Catacombe di San Gennaro, and pause for some serene contemplation at Cloister of Santa Chiara.

To see other places to visit, traveler tips, and tourist information, go to the Naples trip site.

Traveling by car from Ravello to Naples takes 1.5 hours. Alternatively, you can take a bus. Plan for little chillier nights when traveling from Ravello in September since evenings lows in Naples dip to 20°C. Wrap up your sightseeing on the 1st (Fri) to allow time to take a 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: contemplate the long history of St. Peter's Basilica, explore the ancient world of Colosseum, savor the flavors at Food & Drink, and make a trip to Roman Forum.

For more things to do, maps, ratings, and other tourist information, read our Rome online attractions planner.

Traveling by train from Naples to Rome takes 2 hours. Alternatively, you can drive; or fly. Expect a daytime high around 26°C in October, and nighttime lows around 15°C. Wrap up your sightseeing by early afternoon on the 6th (Wed) 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.