21 days in Italy Itinerary

21 days in Italy Itinerary

Created using Inspirock Italy vacation builder

Plan created by another user. Make it yours
Fly
1
Naples
— 2 nights
Drive
2
Furore
— 4 nights
Unknown
3
Florence
— 2 nights
Drive
4
Arezzo
— 5 nights
Drive
5
Pisa
— 4 nights
Train
6
Milan
— 1 night
Fly

S M T W T F S
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2

2
nights
Naples

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. To see traveler tips, ratings, maps, and more tourist information, use the Naples trip planner.

Chicago, USA to Naples is an approximately 15-hour flight. You can also do a combination of flight and train. The time zone changes from Central Standard Time (CST) to Central European Standard Time (CET), which is usually a 7 hour difference. Traveling from Chicago in October, things will get somewhat warmer in Naples: highs are around 74°F and lows about 58°F. You'll set off for Furore on the 16th (Wed).

Things to do in Naples

Tours · Historic Sites · Outdoors · Nightlife
Find places to stay Oct 14 — 16:

4
nights
Furore

Furore is a town and comune in the province of Salerno in the Campania region of south-western Italy. Your cultural itinerary includes sights like Ceramiche Cosmolena di Margherita di Palma and Centro Storico Ravello. Visiting Ravello-Minori Walk and Ravello - Atrani Walk will get you outdoors. Explore the numerous day-trip ideas around Furore: Castello di San Nicola de Thoro-Plano (in Maiori) and Grotte di Castelcivita (in Castelcivita). The adventure continues: ponder the design of Fontana sant'Andrea.

To find ratings, reviews, maps, and tourist information, use the Furore tour itinerary builder website.

Getting from Naples to Furore by car takes about 1.5 hours. In October, daily temperatures in Furore can reach 73°F, while at night they dip to 63°F. On the 20th (Sun), you'll travel to Florence.

Things to do in Furore

Parks · Outdoors · Trails · Historic Sites

Side Trips

Find places to stay Oct 16 — 20:

2
nights
Florence

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Kick off your visit on the 20th (Sun): contemplate in the serene atmosphere at The Baptistery of St. John and then pause for some photo ops at Loggia dei Lanzi. On the 21st (Mon), you'll have a packed day of sightseeing: contemplate the long history of Basilica of Santa Croce, admire the masterpieces at Florence Academy of Fine Arts, snap pictures at Ponte Vecchio, then make a trip to Piazzale Michelangelo, then get great views at Basilica San Miniato al Monte, and finally take in the architecture and atmosphere at Cathedral of Santa Maria del Fiore.

For other places to visit, ratings, and tourist information, go to the Florence road trip planning app.

Traveling by journey from Furore to Florence takes 6 hours. Alternatively, you can drive; or do a combination of car and flight. Expect slightly colder evenings in Florence when traveling from Furore in October, with lows around 54°F. Wrap up your sightseeing by early afternoon on the 22nd (Tue) to allow time for the car ride to Arezzo.

Things to do in Florence

Historic Sites · Museums

Side Trip

Find places to stay Oct 20 — 22:

5
nights
Arezzo

Ancient City

Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
Appreciate the collections at Anghiari and Museo Madonna del Parto. Eschew the tourist crowds and head to Arezzo Cathedral and Museo dei Mezzi di Comunicazione. You'll find plenty of places to visit near Arezzo: Montalcino (Winery Solaria Patrizia Cencioni & Poggio Rubino), Cantalici (in Gaiole in Chianti) and Sansepolcro (Museo Civico di Sansepolcro & Cattedrale di San Giovanni Evangelista). There's lots more to do: contemplate in the serene atmosphere at San Francesco, Arezzo, take in the architecture and atmosphere at Chiesa dei SS Michele e Adriano, see the interesting displays at Museo Archeologico, and contemplate the long history of Acquedotto Romano.

To see maps, photos, where to stay, and tourist information, read Arezzo online sightseeing planner.

You can drive from Florence to Arezzo in 1.5 hours. Alternatively, you can take a train; or take a bus. Finish your sightseeing early on the 27th (Sun) so you can drive to Pisa.

Things to do in Arezzo

Museums · Historic Sites · Wineries

Side Trips

Find places to stay Oct 22 — 27:

4
nights
Pisa

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Appreciate the collections at Palazzo Blu and Museo Nazionale della Certosa Monumentale di Calci. Eschew the tourist crowds and head to Duomo di Pisa and Baptistery of St. John. Venture out of the city with trips to Volterra (Cathedral of Santa Maria Assunta & Palazzo Viti) and Sacro Monte San Vivaldo (in San Vivaldo). Next up on the itinerary: appreciate the extensive heritage of Knights’ Square, take in the spiritual surroundings of Chiesa di San Michele in Borgo, contemplate the long history of Camposanto, and admire the masterpieces at Museo delle Sinopie.

To find reviews, traveler tips, more things to do, and tourist information, read our Pisa trip site.

You can drive from Arezzo to Pisa in 2 hours. Another option is to take a train. In October, daily temperatures in Pisa can reach 71°F, while at night they dip to 54°F. Wrap up your sightseeing on the 31st (Thu) early enough to take a train to Milan.

Things to do in Pisa

Historic Sites · Museums · Shopping · Neighborhoods

Side Trips

Find places to stay Oct 27 — 31:

1
night
Milan

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.
Kick off your visit on the 31st (Thu): contemplate in the serene atmosphere at Duomo di Milano, take in the spiritual surroundings of Certosa di Pavia, and then take in the architecture and atmosphere at Chiesa di Santa Maria presso San Satiro.

To find maps, reviews, more things to do, and tourist information, read our Milan trip itinerary builder.

You can take a train from Pisa to Milan in 3 hours. Alternatively, you can drive; or fly. Expect a bit cooler weather when traveling from Pisa in October: highs in Milan hover around 65°F, while lows dip to 52°F. Wrap up your sightseeing on the 1st (Fri) early enough to travel back home.

Things to do in Milan

Historic Sites

Side Trips

Find places to stay Oct 31 — Nov 1:

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.

Province of Arezzo travel guide

4.3
Sacred & Religious Sites · Landmarks · Specialty Museums
Arezzo is a city and comune in Italy, capital of the province of the same name located in Tuscany. Arezzo is about 80km southeast of Florence at an elevation of 296m above sea level. It is also 30 km west of Città di Castello. In 2013 the population was about 99,000.HistoryDescribed by Livy as one of the Capitae Etruriae (Etruscan capitals), Arezzo (Aritim in Etruscan) is believed to have been one of the twelve most important Etruscan cities—the so-called Dodecapolis, part of the Etruscan League. Etruscan remains establish that the acropolis of San Cornelio, a small hill next to that of San Donatus, was occupied and fortified in the Etruscan period. There is other significant Etruscan evidence: parts of walls, an Etruscan necropolis on Poggio del Sole (still named "Hill of the Sun"), and most famously, the two bronzes, the "Chimera of Arezzo" (5th century BC) and the "Minerva" (4th century BC) which were discovered in the 16th century and taken to Florence. Increasing trade connections with Greece also brought some elite goods to the Etruscan nobles of Arezzo: the krater painted by Euphronios ca 510 BC depicting a battle against Amazons (in the Museo Civico, Arezzo 1465) is unsurpassed.

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Province of Pisa travel guide

4
Observation Decks · Sacred & Religious Sites · Landmarks
Pisa is a city in the Tuscany region of Central Italy straddling the Arno just before it empties into the Ligurian Sea. It is the capital city of the Province of Pisa. Although Pisa is known worldwide for its leaning tower (the bell tower of the city's cathedral), the city of over 91,104 residents (around 200,000 with the metropolitan area) contains more than 20 other historic churches, several medieval palaces and various bridges across the Arno. Much of the city's architecture was financed from its history as one of the Italian maritime republics.The city is also home of the University of Pisa, which has a history going back to the 12th century and also has the Scuola Normale Superiore di Pisa, founded by Napoleon in 1810, and its offshoot, the Sant'Anna School of Advanced Studies as the best sanctioned Superior Graduate Schools in Italy.<ref name="gradscuola/">Scuola Superiore Sant'Anna di Pisa Information statisticsHistoryAncient timesThe origin of the name, Pisa, is a mystery. While the origin of the city had remained unknown for centuries, the Pelasgi, the Greeks, the Etruscans, and the Ligurians had variously been proposed as founders of the city (for example, a colony of the ancient city of Pisa, Greece). Archaeological remains from the 5th century BC confirmed the existence of a city at the sea, trading with Greeks and Gauls. The presence of an Etruscan necropolis, discovered during excavations in the '' in 1991, confirmed its Etruscan origins.

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