22 days in Italy Itinerary

22 days in Italy Itinerary

Created using Inspirock Italy trip planner
Make it your trip
Drive
1
Venice
— 3 nights
Fly
2
Positano
— 4 nights
Drive
3
Rome
— 4 nights
Drive
4
Assisi
— 1 night
Drive
5
Siena
— 3 nights
Drive
6
Florence
— 4 nights
Train
7
Milan
— 2 nights
Drive

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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.
Venice is known for sightseeing, historic sites, and museums. Your trip includes some of its best attractions: contemplate the waterfront views at Canal Grande, steep yourself in history at Ponte dei Sospiri, take in the views from Ponte di Rialto, and pause for some serene contemplation at San Giorgio Maggiore.

For where to stay, ratings, maps, and tourist information, read Venice itinerary maker.

Erfurt, Germany to Venice is an approximately 10-hour car ride. Plan for somewhat warmer temperatures traveling from Erfurt in October, with highs in Venice at 22°C and lows at 12°C. Wrap up your sightseeing on the 4th (Tue) to allow time to fly to Positano.
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Historic Sites · Tours · Museums · Nature
Find places to stay Oct 1 — 4:

Positano — 4 nights

Often referred to as the gem of the Amalfi Coast, Positano remains one of southern Italy's most sought-after vacation locales, thanks to its hillside location and picturesque, pastel buildings.
You'll find plenty of places to visit near Positano: Amalfi (Fontana sant'Andrea, Duomo di Sant'Andrea, &more), Sorrento (Cattedrale di Sorrento, Food Tours, &more) and Ravello (Ceramiche Cosmolena di Margherita di Palma, Villa Cimbrone Gardens, &more). And it doesn't end there: cruise along Amalfi Coast, get a new perspective on things with Boat Tours & Water Sports, enjoy the sand and surf at Fornillo, and enjoy breathtaking views from Torre di Grado.

To find more things to do, traveler tips, and other tourist information, you can read our Positano online day trip planner.

Fly from Venice to Positano in 3 hours. Alternatively, you can drive; or do a combination of train and bus. Traveling from Venice in October, things will get somewhat warmer in Positano: highs are around 26°C and lows about 20°C. Wrap up your sightseeing on the 8th (Sat) to allow time to drive to Rome.
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Outdoors · Historic Sites · Tours · Parks
Side Trips
Find places to stay Oct 4 — 8:

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: take in the architecture and atmosphere at St. Peter's Basilica, admire the masterpieces at Galleria Borghese, steep yourself in history at Roman Forum, and delve into the distant past at Colosseum.

To see where to stay, traveler tips, photos, and more tourist information, use the Rome road trip planning app.

Getting from Positano to Rome by car takes about 3.5 hours. Other options: do a combination of bus and train; or take a bus. Traveling from Positano in October, expect slightly colder with lows of 15°C in Rome. Cap off your sightseeing on the 12th (Wed) early enough to go by car to Assisi.
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Historic Sites · Museums · Tours · Neighborhoods
Side Trip
Find places to stay Oct 8 — 12:

Assisi — 1 night

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Start off your visit on the 13th (Thu): learn about winemaking at Tili Vini Societa Agricola, take in the spiritual surroundings of Eremo delle Carceri, then 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 see ratings, photos, maps, and other tourist information, read Assisi online tour itinerary planner.

Traveling by car from Rome to Assisi takes 2.5 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 24°C in October, and nighttime lows around 12°C. Cap off your sightseeing on the 13th (Thu) early enough to go by car to Siena.
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Wineries · Historic Sites
Find places to stay Oct 12 — 13:

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.
Step out of Siena to go to San Gimignano and see Guardastelle Vineyard, which is approximately 52 minutes away. Next up on the itinerary: savor the flavors at Food & Drink, deepen your understanding at Scuola di Cucina di Lella, browse the exhibits of Palazzo Pubblico and Museo Civico, and don't miss a visit to Piazza del Campo.

To see reviews, more things to do, maps, and tourist information, refer to the Siena trip planner.

Drive from Assisi to Siena in 2 hours. Alternatively, you can take a bus; or take a train. In October, daily temperatures in Siena can reach 26°C, while at night they dip to 15°C. Wrap up your sightseeing on the 16th (Sun) to allow time to drive to Florence.
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Wineries · Tours · Museums · Historic Sites
Side Trip
Find places to stay Oct 13 — 16:

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.
Florence is known for sightseeing, museums, and historic sites. Your trip includes some of its best attractions: admire the masterpieces at Florence Academy of Fine Arts, take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, see the interesting displays at Pitti Palace, and don't miss a visit to Piazzale Michelangelo.

To find photos, where to stay, ratings, and other tourist information, read our Florence day trip planning tool.

You can drive from Siena to Florence in 1.5 hours. Alternatively, you can take a bus; or take a train. In October, daily temperatures in Florence can reach 25°C, while at night they dip to 14°C. Wrap up your sightseeing on the 20th (Thu) to allow time to take a train to Milan.
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Tours · Historic Sites · Wineries · Museums
Side Trip
Find places to stay Oct 16 — 20:

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.
Start off your visit on the 21st (Fri): explore the world behind art at Pinacoteca Ambrosiana, listen to music at La Casa Maledetta, then take in the spiritual surroundings of Duomo di Milano, and finally admire the striking features of Galleria Vittorio Emanuele II. On the 22nd (Sat), you'll have a packed day of sightseeing: contemplate the long history of Castello Sforzesco and then stroll the grounds of Monumental Cemetery.

For other places to visit, maps, photos, and other tourist information, use the Milan trip itinerary planning website.

Take a train from Florence to Milan in 2.5 hours. Alternatively, you can drive; or take a bus. Traveling from Florence in October, expect nights in Milan to be about the same, around 13°C, while days are a bit cooler, around 21°C. Finish your sightseeing early on the 22nd (Sat) to allow enough time to drive back home.
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Historic Sites · Museums · Fun & Games · Nightlife
Find places to stay Oct 20 — 22:

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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