28 days in Italy Itinerary

28 days in Italy Itinerary

Created using Inspirock Italy trip planner

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

S M T W T F S
15
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17
18
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21
22
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25
26
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28
29
30
31
1
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18

Milan

— 2 nights

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.
You'll find plenty of places to visit near Milan: Tremezzina (Villa del Balbianello & Villa Carlotta). The adventure continues: take in the architecture and atmosphere at Duomo di Milano, admire the landmark architecture of Galleria Vittorio Emanuele II, take an in-depth tour of Pinacoteca Ambrosiana, and steep yourself in history at Castello Sforzesco.

To find ratings, reviews, traveler tips, and other tourist information, go to the Milan trip itinerary planning site.

Oslo, Norway to Milan is an approximately 6-hour flight. You can also drive; or take a train. Prepare for somewhat warmer weather when traveling from Oslo in May: high temperatures in Milan hover around 26°C and lows are around 15°C. Cap off your sightseeing on the 21st (Sat) early enough to catch the train to Florence.

Things to do in Milan

Historic Sites · Museums · Parks · Shopping

Side Trip

Find places to stay May 19 — 21:

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 (Leaning Tower of Pisa & Museo Aviotruppe Esercito Italiano). And it doesn't end there: explore the world behind art at Florence Academy of Fine Arts, appreciate the extensive heritage of Piazza del Duomo, examine the collection at Pitti Palace, and take in the views from Ponte Vecchio.

For more things to do, other places to visit, and more tourist information, you can read our Florence holiday site.

You can take a train from Milan to Florence in 2.5 hours. Other options are to drive; or take a bus. In May, plan for daily highs up to 25°C, and evening lows to 13°C. Finish your sightseeing early on the 25th (Wed) so you can drive to Siena.

Things to do in Florence

Historic Sites · Museums · Parks · Shopping

Side Trip

Find places to stay May 21 — 25:

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.
Venture out of the city with trips to Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate) and Castiglion del Bosco Winery (in Montalcino). There's still lots to do: savor the flavors at Food & Drink, don't miss a visit to Piazza del Campo, contemplate the long history of San Francesco, and ponder the world of politics at Palazzo Pubblico and Museo Civico.

To find where to stay, other places to visit, ratings, and other tourist information, read our Siena trip itinerary site.

Getting from Florence to Siena by car takes about 1.5 hours. Other options: take a bus; or take a train. In May in Siena, expect temperatures between 27°C during the day and 13°C at night. Finish up your sightseeing early on the 28th (Sat) so you can go by car to Assisi.

Things to do in Siena

Wineries · Historic Sites · Tours · Museums

Side Trip

Find places to stay May 25 — 28:

Assisi

— 2 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
On the 29th (Sun), take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi, admire the striking features of Santa Maria sopra Minerva, then explore the world behind art at Studio Moretti Caselli, and finally see the interesting displays at Museo della Porziuncola. Keep things going the next day: do a tasting at Tili Vini Societa Agricola, take in the architecture and atmosphere at Cattedrale di San Rufino, then contemplate in the serene atmosphere at Eremo delle Carceri, and finally explore the historical opulence of Rocca Maggiore.

To find where to stay, reviews, maps, and more tourist information, go to the Assisi online travel route planner.

Traveling by car from Siena to Assisi takes 2 hours. Alternatively, you can take a bus; or take a train. In May, daytime highs in Assisi are 26°C, while nighttime lows are 13°C. Finish up your sightseeing early on the 30th (Mon) so you can go by car to Rome.

Things to do in Assisi

Historic Sites · Museums · Wineries

Side Trip

Find places to stay May 28 — 30:

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 trip includes some of its best attractions: explore the ancient world of Pantheon, pause for some serene contemplation at St. Peter's Basilica, contemplate the long history of Palatine Hill, and explore the world behind art at Galleria Borghese.

To find photos, ratings, where to stay, and other tourist information, you can read our Rome trip planner.

You can drive from Assisi to Rome in 2.5 hours. Other options are to take a train; or take a bus. Expect a bit warmer evenings in Rome when traveling from Assisi in May, with lows around 17°C. Finish your sightseeing early on the 4th (Sat) to allow enough time to take a train to Naples.

Things to do in Rome

Historic Sites · Museums · Tours · Neighborhoods

Side Trip

Find places to stay May 30 — Jun 4:

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: Pompeii (Villa dei Misteri & Lupanar) and Salerno (Duomo di Salerno, Giardino della Minerva, &more). There's lots more to do: make a trip to Pompeii Archaeological Park, take in the architecture and atmosphere at Cloister of Santa Chiara, examine the collection at Museo Archeologico Nazionale di Napoli, and get engrossed in the history at Museo e Real Bosco di Capodimonte.

To see photos, other places to visit, reviews, and other tourist information, use the Naples sightseeing planning tool.

You can take a train from Rome to Naples in 2 hours. Alternatively, you can drive; or fly. In June, daily temperatures in Naples can reach 32°C, while at night they dip to 22°C. Wrap up your sightseeing on the 8th (Wed) to allow time to drive to Ravello.

Things to do in Naples

Historic Sites · Transportation · Outdoors · Tours

Side Trips

Find places to stay Jun 4 — 8:

Ravello

— 3 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: Positano (Boat Tours & Water Sports, Il Sentiero Degli Dei, &more). The adventure continues: indulge your senses at Amalfi Coast Drive, admire the natural beauty at Villa Cimbrone Gardens, take in the spiritual surroundings of Duomo di Ravello, and cruise along Amalfi Coast.

To find where to stay, photos, ratings, and other tourist information, go to the Ravello tour planning site.

Getting from Naples to Ravello by car takes about 1.5 hours. Other options: take a bus. Traveling from Naples in June, plan for somewhat warmer nights in Ravello, with lows around 26°C. Finish up your sightseeing early on the 11th (Sat) so you can catch the flight to Venice.

Things to do in Ravello

Outdoors · Parks · Tours · Historic Sites

Side Trips

Find places to stay Jun 8 — 11:

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: Scrovegni Chapel (in Padua) and Verona (Basilica di San Zeno Maggiore, Arena di Verona, &more). There's still lots to do: explore the activities along Canal Grande, steep yourself in history at St Mark's Campanile, get to know the fascinating history of Piazza San Marco, and take in the local highlights with Walking tours.

For other places to visit, where to stay, more things to do, and other tourist information, read our Venice road trip app.

Traveling by flight from Ravello to Venice takes 3 hours. Alternatively, you can do a combination of taxi and train; or drive. Traveling from Ravello in June, expect little chillier with lows of 20°C in Venice. Wrap up your sightseeing on the 15th (Wed) to allow time to fly back home.

Things to do in Venice

Historic Sites · Museums · Tours · Parks

Side Trips

Find places to stay Jun 11 — 15:

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.