12 days in Italy Itinerary

12 days in Italy Itinerary

Created using Inspirock Italy trip planner

Make it your trip
Fly
1
Milan
— 2 nights
Train to Firenze Santa Maria Novella, Bus to Siena
2
Siena
— 2 nights
Train to Meta, Bus to Positano
3
Positano
— 2 nights
Bus to Meta, Train to Florence
4
Florence
— 2 nights
Train
5
Cinque Terre
— 1 night
Train
6
Varenna
— 1 night
Train
7
Milan
Fly

S M T W T F S
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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 12th (Tue): take in the architecture and atmosphere at Duomo di Milano, don't miss a visit to Piazza del Duomo, and then pause for some serene contemplation at Basilica di Sant'Ambrogio. On the next day, take in the spiritual surroundings of Il Cenacolo, explore the historical opulence of Castello Sforzesco, and then make a trip to Galleria Vittorio Emanuele II.

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

New York City, USA to Milan is an approximately 12-hour flight. The time zone changes from Eastern Standard Time (EST) to Central European Standard Time (CET), which is usually a 6 hour difference. Prepare for a bit cooler weather when traveling from New York City in October: high temperatures in Milan hover around 65°F and lows are around 52°F. Cap off your sightseeing on the 14th (Thu) early enough to go by car to Siena.

Things to do in Milan

Historic Sites · Shopping · Museums
Find places to stay Oct 12 — 14:

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 14th (Thu), take in the spiritual surroundings of Battistero di San Giovanni, contemplate the long history of Centro Storico di Siena, then pause for some serene contemplation at Duomo di Siena, and finally don't miss a visit to Piazza del Campo. Keep things going the next day: ponder the world of politics at Palazzo Pubblico and Museo Civico, awaken your taste buds at some of the top wineries in the area, and then take in panoramic vistas at Torre del Mangia.

For more things to do, ratings, reviews, and tourist information, go to the Siena trip itinerary builder.

Drive from Milan to Siena in 4 hours. Alternatively, you can take a train; or do a combination of train and bus. When traveling from Milan in October, plan for somewhat warmer days and about the same nights in Siena: temperatures range from 73°F by day to 56°F at night. Cap off your sightseeing on the 16th (Sat) early enough to go by car to Positano.

Things to do in Siena

Historic Sites · Tours · Wineries · Museums
Find places to stay Oct 14 — 16:

Positano

— 2 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.
On the 16th (Sat), get a new perspective on things with Boat Tours & Water Sports.

To see where to stay, traveler tips, ratings, and tourist information, go to the Positano route planner.

Traveling by car from Siena to Positano takes 5 hours. Alternatively, you can do a combination of train and bus; or take a bus. Traveling from Siena in October, Positano is a bit warmer at night with lows of 63°F. Cap off your sightseeing on the 18th (Mon) early enough to travel to Florence.

Things to do in Positano

Outdoors · Tours · Historic Sites
Find places to stay Oct 16 — 18:

Florence

— 2 nights

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 18th (Mon): get a taste of the local shopping with Mercato Centrale, take in the architecture and atmosphere at Basilica of Santa Croce, then take in the spiritual surroundings of The Baptistery of St. John, and finally make a trip to Piazza della Signoria. Here are some ideas for day two: take in the views from Ponte Vecchio, make a trip to Piazzale Michelangelo, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, then appreciate the extensive heritage of Piazza del Duomo, and finally explore the world behind art at Florence Academy of Fine Arts.

For other places to visit, traveler tips, maps, and other tourist information, you can read our Florence trip itinerary tool.

Traveling by combination of flight and train from Positano to Florence takes 5 hours. Alternatively, you can drive; or do a combination of bus and train. Traveling from Positano in October, Florence is little chillier at night with lows of 54°F. Wrap up your sightseeing on the 20th (Wed) to allow time to drive to Cinque Terre.

Things to do in Florence

Historic Sites · Museums · Shopping
Find places to stay Oct 18 — 20:

Cinque Terre

— 1 night

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Start off your visit on the 20th (Wed): get into the urban bustle at Vernazza, tour the pleasant surroundings at Footpath Monterosso - Vernazza, and then discover the deep blue sea with Enjoy Cinqueterre Boat Tours.

To find maps, more things to do, where to stay, and tourist information, read Cinque Terre trip itinerary tool.

Traveling by car from Florence to Cinque Terre takes 2.5 hours. Alternatively, you can take a train. In October, daily temperatures in Cinque Terre can reach 71°F, while at night they dip to 54°F. Cap off your sightseeing on the 21st (Thu) early enough to go by car to Varenna.

Things to do in Cinque Terre

Outdoors · Tours · Wildlife · Trails
Find places to stay Oct 20 — 21:

Varenna

— 1 night
Varenna is a comune (municipality) on Lake Como in the Province of Lecco in the Italian region Lombardy, located about 60km north of Milan and about 20km northwest of Lecco.Varenna was founded by local fishermen in 769, and was later allied of the commune of Milan. On the 21st (Thu), pause for some serene contemplation at Chiesa di San Giorgio and then admire the landmark architecture of Villa Monastero.

For reviews, more things to do, photos, and more tourist information, use the Varenna trip builder site.

Drive from Cinque Terre to Varenna in 4 hours. Alternatively, you can take a train. Expect a bit cooler temperatures when traveling from Cinque Terre in October; daily highs in Varenna reach 64°F and lows reach 49°F. Finish your sightseeing early on the 22nd (Fri) to allow enough time to drive to Milan.

Things to do in Varenna

Historic Sites
Find places to stay Oct 21 — 22:
Highlights from your trip

Milan

Fashion Capital of World

Start off your visit on the 22nd (Fri): take in the spiritual surroundings of Piazza di Santa Maria delle Grazie, 2 and then explore the world behind art at Pinacoteca di Brera.

To find more things to do, other places to visit, reviews, and more tourist information, refer to the Milan travel route planner.

You can drive from Varenna to Milan in 1.5 hours. Alternatively, you can take a train. Finish your sightseeing early on the 22nd (Fri) to allow enough time to fly back home.

Things to do in Milan

Museums · Historic Sites
Find places to stay Oct 22 — 23:
Highlights from your 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.

Tuscany travel guide

4.4
Landmarks · Art Museums · Sacred & Religious Sites
Birthplace of the Italian Renaissance
Known for its landscapes, traditions, and history, Tuscany possesses an unparalleled artistic legacy that continues to influence world culture. Regarded as the birthplace of the Italian Renaissance, the region boasts a lengthy list of attractions, including world-class museums, art galleries, and archeological sites. With a distinct culture and a very strong linguistic identity, this region is sometimes referred to as a nation within a nation. A land of picture-postcard areas, Tuscany contains plenty of places to visit on your holiday, with seven World Heritage Sites, including the historic town centers of Florence and Siena. With more than 120 protected nature preserves, Tuscany is not only a land of culture and historic monuments, but also a great place to discover and enjoy the Italian outdoors. Take it slowly here (as the locals do), and give yourself plenty of time to get to know the local culture and cuisine of Tuscany's medieval towns and ancient villages.

Amalfi Coast travel guide

4.2
Sacred & Religious Sites · Landmarks · Gardens
Renowned for its beautiful landscape and medieval fishing villages that cling precariously to the Mediterranean cliffs, the Amalfi Coast is one of Italy's top vacation destinations. This World Heritage Site stretches for about 50 km (30 mi) on the southern side of the Sorrentine peninsula and offers numerous places to visit, from terraced lemon gardens and whitewashed villas to cliff-top views of the sea. Explore the coastline's towns, bays, and resorts. During the peak tourist season, the Amalfi Coast's single seaside road is often jammed with dozens of buses. For that reason, the ubiquitous scooter may be the best way to get around and sightsee. You can also access quite a bit by bicycle.

Lake Como travel guide

4.2
Gardens · Architectural Buildings · Churches
A favorite vacation spot for more than a century, Lake Como was once an exclusive retreat for local aristocrats and wealthy people. It is not only one of Europe's most beautiful lakes, but also one of the deepest at more than 400 m (1,300 ft). Surrounded by elegant villas, the lake has become a popular holiday destination for tourists because of its range of attractions, from landscapes, wildlife, and spas, to activities like sailing, windsurfing, and kite-surfing. The area has been an inspiration for artists since Roman times. English poet Percy Bysshe Shelley wrote, "This lake exceeds anything I ever beheld in beauty…It is long and narrow and has the appearance of a mighty river winding among the mountains and the forests."