20 days in Italy Itinerary

20 days in Italy Itinerary

Created using Inspirock Italy trip planner

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

S M T W T F S
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Rome

— 3 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: delve into the distant past at Pantheon, explore the world behind art at Galleria Borghese, admire the local landmark of Trevi Fountain, and contemplate the long history of Roman Forum.

Discover how to plan a Rome trip in just a few steps with Inspirock's itinerary builder.

Amman, Jordan to Rome is an approximately 7-hour flight. You can also drive. Traveling from Amman to Rome, you'll gain 1 hour due to the time zone difference. Traveling from Amman in May, you will find days in Rome are slightly colder (28°C), and nights are about the same (17°C). Wrap up your sightseeing on the 11th (Wed) to allow time to take a train to Naples.

Things to do in Rome

Historic Sites · Museums · Tours · Neighborhoods

Side Trip

Find places to stay May 8 — 11:

Naples

— 2 nights
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Start off your visit on the 12th (Thu): take in the spiritual surroundings of Museo Cappella Sansevero, pause for some serene contemplation at Duomo di Napoli, then get engrossed in the history at Museo e Real Bosco di Capodimonte, and finally see the interesting displays at Museo Archeologico Nazionale di Napoli. Get ready for a full day of sightseeing on the 13th (Fri): explore the different monuments and memorials at Catacombe di San Gennaro, delve into the distant past at Odeon - Teatro Piccolo, then steep yourself in history at Villa dei Misteri, and finally explore the ancient world of Pompeii Archaeological Park.

For maps, more things to do, ratings, and other tourist information, use the Naples itinerary app.

Traveling by train from Rome to Naples takes 2 hours. Alternatively, you can drive; or fly. In May in Naples, expect temperatures between 27°C during the day and 17°C at night. Wrap up your sightseeing on the 13th (Fri) early enough to drive to Amalfi.

Things to do in Naples

Historic Sites · Museums

Side Trip

Find places to stay May 11 — 13:

Amalfi

— 3 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.
Venture out of the city with trips to Positano (Il Sentiero Degli Dei, Fornillo, &more). And it doesn't end there: admire the natural beauty at Villa Cimbrone Gardens, take in the spiritual surroundings of Duomo di Ravello, steep yourself in history at Villa Rufolo, and pause for some serene contemplation at Duomo di Sant'Andrea.

Plan my day in Amalfi using traveler tips and tourist information provided by Inspirock.

Getting from Naples to Amalfi by car takes about 1.5 hours. Other options: take a bus; or do a combination of train and bus. Traveling from Naples in May, expect a bit warmer with lows of 21°C in Amalfi. Wrap up your sightseeing on the 16th (Mon) early enough to fly to Milan.

Things to do in Amalfi

Parks · Outdoors · Historic Sites · Tours

Side Trips

Find places to stay May 13 — 16:

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.
Start off your visit on the 17th (Tue): get a taste of the local shopping with Galleria Vittorio Emanuele II, then take in the spiritual surroundings of Duomo di Milano, then pause for some serene contemplation at Basilica San Lorenzo Maggiore, and finally get engrossed in the history at Pinacoteca Ambrosiana.

Plan a Milan trip in moments using our itinerary builder.

Traveling by flight from Amalfi to Milan takes 3 hours. Alternatively, you can do a combination of taxi and train; or drive. Traveling from Amalfi in May, plan for little chillier nights in Milan, with lows around 15°C. Wrap up your sightseeing on the 17th (Tue) to allow time to drive to Venice.

Things to do in Milan

Museums · Historic Sites · Shopping
Find places to stay May 16 — 17:

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.
Change things up with a short trip to Scrovegni Chapel in Padua (about 54 minutes away). There's still lots to do: contemplate the waterfront views at Canal Grande, snap pictures at Ponte di Rialto, take in the local highlights with Walking tours, and contemplate the long history of Ponte dei Sospiri.

To find where to stay, reviews, traveler tips, and more tourist information, you can read our Venice online tour itinerary builder.

You can drive from Milan to Venice in 3 hours. Other options are to take a train; or take a bus. In May in Venice, expect temperatures between 26°C during the day and 15°C at night. Cap off your sightseeing on the 20th (Fri) early enough to go by car to Siena.

Things to do in Venice

Historic Sites · Museums · Tours · Parks

Side Trip

Find places to stay May 17 — 20:

Siena

— 2 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
On the 21st (Sat), explore the world behind art at Museo dell'Opera Metropolitana, savor the flavors at Food & Drink, and then take in the spiritual surroundings of San Francesco. Get ready for a full day of sightseeing on the next day: make a trip to Piazza del Campo, then contemplate the long history of Centro Storico di Siena, then take in the architecture and atmosphere at Duomo di Siena, and finally ponder the world of politics at Palazzo Pubblico and Museo Civico.

To find other places to visit, reviews, photos, and tourist information, refer to the Siena trip app.

Getting from Venice to Siena by car takes about 3.5 hours. Other options: take a train; or do a combination of train and bus. In May, daily temperatures in Siena can reach 27°C, while at night they dip to 13°C. Cap off your sightseeing on the 22nd (Sun) early enough to go by car to Assisi.

Things to do in Siena

Historic Sites · Wineries · Tours · Museums
Find places to stay May 20 — 22:

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 23rd (Mon): do a tasting at Tili Vini Societa Agricola, take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi, then take in the spiritual surroundings of Basilica di Santa Maria degli Angeli - Porziuncola, then see the interesting displays at Museo della Porziuncola, and finally take in the spiritual surroundings of Eremo delle Carceri.

To see more things to do, traveler tips, where to stay, and other tourist information, go to the Assisi travel site.

Drive from Siena to Assisi in 2 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 26°C in May, and nighttime lows around 13°C. Finish your sightseeing early on the 23rd (Mon) to allow enough time to drive to Florence.

Things to do in Assisi

Historic Sites · Wineries · Museums
Find places to stay May 22 — 23:

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 Florence's surroundings by going to Le Due Torri Torre degli Asinell (in Bologna) and Leaning Tower of Pisa (in Pisa). There's lots more to do: admire the masterpieces at Florence Academy of Fine Arts, contemplate in the serene atmosphere at Campanile di Giotto, appreciate the extensive heritage of Piazza del Duomo, and snap pictures at Ponte Vecchio.

To see traveler tips, photos, where to stay, and other tourist information, go to the Florence sightseeing planning tool.

Traveling by car from Assisi to Florence takes 2.5 hours. Alternatively, you can take a train. In May, daily temperatures in Florence can reach 25°C, while at night they dip to 13°C. Cap off your sightseeing on the 27th (Fri) early enough to catch the flight back home.

Things to do in Florence

Historic Sites · Museums · Parks

Side Trips

Find places to stay May 23 — 27:

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.