19 days in Italy Itinerary

19 days in Italy Itinerary

Created using Inspirock Italy trip itinerary planner

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

S M T W T F S
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Venice

— 2 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.
Venture out of the city with trips to Padua (Scrovegni Chapel & Chiesa degli Eremitani). There's still lots to do: explore the activities along Canal Grande, snap pictures at Ponte di Rialto, admire the landmark architecture of Basilica di San Marco, and take in the architecture and atmosphere at San Giorgio Maggiore.

To find photos, maps, where to stay, and other tourist information, read Venice trip itinerary planning tool.

Seattle, USA to Venice is an approximately 16-hour flight. Traveling from Seattle to Venice, you'll lose 9 hours due to the time zone difference. In September, plan for daily highs up to 77°F, and evening lows to 59°F. Cap off your sightseeing on the 20th (Tue) early enough to travel to Naples.

Things to do in Venice

Historic Sites · Museums · Tours · Nature

Side Trip

Find places to stay Sep 17 — 20:

Naples

— 2 nights
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Kick off your visit on the 21st (Wed): take in the architecture and atmosphere at Duomo di Salerno, then learn about winemaking at Bosco de Medici Winery, then contemplate the long history of Villa dei Misteri, and finally delve into the distant past at Pompeii Archaeological Park. Here are some ideas for day two: stroll the grounds of Catacombe di San Gennaro, get engrossed in the history at Museo e Real Bosco di Capodimonte, examine the collection at Museo Archeologico Nazionale di Napoli, then pause for some serene contemplation at Duomo di Napoli, and finally make a trip to Piazza del Plebiscito.

For photos, other places to visit, traveler tips, and more tourist information, refer to the Naples trip itinerary planner.

Getting from Venice to Naples by flight takes about 3.5 hours. Other options: take a train; or drive. In September in Naples, expect temperatures between 80°F during the day and 64°F at night. Cap off your sightseeing on the 22nd (Thu) early enough to go by car to Positano.

Things to do in Naples

Historic Sites · Museums · Wineries

Side Trips

Find places to stay Sep 20 — 22:

Positano

— 3 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.
Explore Positano's surroundings by going to Ravello (Villa Cimbrone Gardens, Villa Rufolo, &more), Amalfi (Fontana sant'Andrea, Duomo di Sant'Andrea, &more) and Fiordo di Furore (in Furore). Next up on the itinerary: get a new perspective on things with Boat Tours & Water Sports, cool off at Fornillo, enjoy breathtaking views from Torre di Grado, and take some stellar pictures from Il Sentiero Degli Dei.

To see photos, more things to do, ratings, and more tourist information, use the Positano trip itinerary planner.

Traveling by car from Naples to Positano takes 1.5 hours. Alternatively, you can take a bus. In September in Positano, expect temperatures between 80°F during the day and 68°F at night. Wrap up your sightseeing on the 25th (Sun) to allow time to drive to Rome.

Things to do in Positano

Outdoors · Historic Sites · Parks · Beaches

Side Trips

Find places to stay Sep 22 — 25:

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 plan includes some of its best attractions: steep yourself in history at Colosseum, pause for some serene contemplation at Pantheon, explore the world behind art at Galleria Borghese, and ponder the design of Trevi Fountain.

For photos, reviews, where to stay, and more tourist information, you can read our Rome road trip planner.

Traveling by car from Positano to Rome takes 3.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. Traveling from Positano in September, expect little chillier with lows of 60°F in Rome. Wrap up your sightseeing on the 28th (Wed) early enough to drive to Siena.

Things to do in Rome

Historic Sites · Museums · Neighborhoods

Side Trip

Find places to stay Sep 25 — 28:

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 29th (Thu), don't miss a visit to Piazza del Campo and then indulge your taste buds at Food & Drink. Get ready for a full day of sightseeing on the 30th (Fri): ponder the world of politics at Palazzo Pubblico and Museo Civico, deepen your understanding at Scuola di Cucina di Lella, then take in the architecture and atmosphere at Duomo di Siena, then admire the masterpieces at Museo dell'Opera Metropolitana, and finally contemplate in the serene atmosphere at San Francesco.

To see traveler tips and other tourist information, read our Siena online route maker.

You can drive from Rome to Siena in 2.5 hours. Alternatively, you can take a bus; or take a train. In September, daytime highs in Siena are 81°F, while nighttime lows are 61°F. Finish your sightseeing early on the 30th (Fri) so you can drive to Florence.

Things to do in Siena

Wineries · Tours · Historic Sites · Museums
Find places to stay Sep 28 — 30:

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 museums, historic sites, and shopping. Your plan includes some of its best attractions: explore the world behind art at Florence Academy of Fine Arts, snap pictures at Ponte Vecchio, make a trip to Piazzale Michelangelo, and see the interesting displays at Pitti Palace.

To find other places to visit, more things to do, where to stay, and more tourist information, you can read our Florence online itinerary planner.

Drive from Siena to Florence in 1.5 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 78°F in September, and nighttime lows around 59°F. Finish up your sightseeing early on the 4th (Tue) so you can catch the train to Milan.

Things to do in Florence

Tours · Historic Sites · Wineries · Museums

Side Trip

Find places to stay Sep 30 — Oct 4:

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.
Kick off your visit on the 5th (Wed): explore the world behind art at Pinacoteca Ambrosiana, take in the architecture and atmosphere at Duomo di Milano, and then admire the landmark architecture of Galleria Vittorio Emanuele II.

To see traveler tips, more things to do, where to stay, and more tourist information, read our Milan road trip planner.

Take a train from Florence to Milan in 2.5 hours. Alternatively, you can drive; or fly. Expect a bit cooler weather when traveling from Florence in October: highs in Milan hover around 65°F, while lows dip to 52°F. Finish your sightseeing early on the 5th (Wed) to allow enough time to travel back home.

Things to do in Milan

Historic Sites · Museums · Shopping
Find places to stay Oct 4 — 5:

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.