36 days in Italy Itinerary

36 days in Italy Itinerary

Created using Inspirock Italy trip planner
Make it your trip
Fly
1
Milan
— 4 nights
Drive
2
Verona
— 3 nights
Drive
3
Venice
— 4 nights
Fly
4
Positano
— 5 nights
Drive
5
Pompeii
— 4 nights
Train
6
Rome
— 5 nights
Drive
7
Assisi
— 2 nights
Drive
8
Siena
— 3 nights
Drive
9
Florence
— 5 nights
Fly

S M T W T F S
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19
20
21
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24
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28
29
30
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2
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4
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Milan — 4 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.
Venture out of the city with trips to Cathedral of Como (Duomo) (in Como), Bellagio (I Giardini di Villa Melzi & Kayaking & Canoeing) and Tremezzina (Villa del Balbianello & Villa Carlotta). The adventure continues: pause for some serene contemplation at Duomo di Milano, see La Casa Maledetta, explore the historical opulence of Castello Sforzesco, and get engrossed in the history at Basilica di Sant'Ambrogio.

To see maps, ratings, photos, and more tourist information, use the Milan trip planner.

Tampa, USA to Milan is an approximately 15-hour flight. The time zone difference when traveling from Tampa to Milan is 6 hours. Plan for little chillier temperatures traveling from Tampa in September, with highs in Milan at 76°F and lows at 57°F. Cap off your sightseeing on the 16th (Sat) early enough to go by car to Verona.
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Museums · Historic Sites · Parks · Outdoors
Side Trips
Find places to stay Sep 12 — 16:

Verona — 3 nights

City of Romeo and Juliet

The famous setting for Shakespeare's star-crossed lovers, Romeo and Juliet, Verona is one of northern Italy's main tourist destinations, largely owing to its incredibly rich artistic heritage.
Venture out of the city with trips to Lago di Garda (in Garda) and Gardaland Park (in Castelnuovo del Garda). There's much more to do: catch a live performance at Arena di Verona, snap pictures at Ponte Pietra, take a stroll through Piazza delle Erbe, and explore the historical opulence of Piazzale Castel San Pietro.

To see where to stay, photos, other places to visit, and other tourist information, you can read our Verona travel app.

Traveling by car from Milan to Verona takes 2 hours. Alternatively, you can take a train. In September in Verona, expect temperatures between 78°F during the day and 58°F at night. Wrap up your sightseeing on the 19th (Tue) to allow time to drive to Venice.
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Historic Sites · Neighborhoods · Shopping · Parks
Side Trips
Find places to stay Sep 16 — 19:

Venice — 4 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 these side-trips from Venice: Scrovegni Chapel (in Padua), PDC Cartizze (in Valdobbiadene) and Toni Doro - Il Prosecco (in Vittorio Veneto). And it doesn't end there: explore the activities along Canal Grande, savor the flavors at Food & Drink, contemplate the long history of Ponte dei Sospiri, and explore the galleries of Peggy Guggenheim Collection.

To find ratings, reviews, maps, and other tourist information, go to the Venice driving holiday planner.

Drive from Verona to Venice in 1.5 hours. Alternatively, you can take a shuttle; or take a train. In September, daytime highs in Venice are 77°F, while nighttime lows are 59°F. Finish your sightseeing early on the 23rd (Sat) to allow enough time to fly to Positano.
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Historic Sites · Museums · Tours · Wineries
Side Trips
Find places to stay Sep 19 — 23:

Positano — 5 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: Torre del Capo di Conca (in Conca dei Marini), Ravello (Ceramiche Cosmolena di Margherita di Palma, Villa Rufolo, &more) and Amalfi (Valle delle Ferriere, Fontana sant'Andrea, &more). There's much more to do: savor the flavors at Food & Drink, pause for some serene contemplation at Cattedrale di Sorrento, get outside with Amalfi Coast, and get a new perspective on things with Boat Tours & Water Sports.

For other places to visit, maps, traveler tips, and tourist information, read our Positano route maker app.

Traveling by flight from Venice to Positano takes 3 hours. Alternatively, you can drive; or do a combination of train and bus. Traveling from Venice in September, plan for a bit warmer nights in Positano, with lows around 68°F. Wrap up your sightseeing on the 28th (Thu) to allow time to drive to Pompeii.
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Outdoors · Historic Sites · Parks · Tours
Side Trips
Find places to stay Sep 23 — 28:

Pompeii — 4 nights

Underground City

Pompeii has been a tourist destination for more than 250 years.
Change things up with these side-trips from Pompeii: Archaeological Park of Paestum (in Paestum), Salerno (Promenade Trieste, Duomo di Salerno, &more) and Ravello (Ravello Arte, Kundry Bottega d'Arte, &more). There's still lots to do: explore the ancient world of Pompeii Archaeological Park, steep yourself in history at House of Menander (Casa del Menandro), learn about winemaking at Bosco de Medici Winery, and admire the landmark architecture of Villa dei Misteri.

Plan my Pompeii trip by asking Inspirock to come up with tips and suggestions.

Traveling by car from Positano to Pompeii takes 1.5 hours. Alternatively, you can take a bus. In September, plan for daily highs up to 80°F, and evening lows to 64°F. Wrap up your sightseeing on the 2nd (Mon) to allow time to take a train to Rome.
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Historic Sites · Outdoors · Tours · Transportation
Side Trips
Find places to stay Sep 28 — Oct 2:

Rome — 5 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Explore Rome's surroundings by going to Macchina di Santa Rosa (in Viterbo) and Culture Discovery Vacations - Cooking Classes & Vacations (in Soriano nel Cimino). There's much more to do: contemplate the long history of St. Peter's Basilica, delve into the distant past at Pantheon, don't miss a visit to Spanish Steps, and admire the masterpieces at Vatican Museums.

To see reviews, traveler tips, more things to do, and other tourist information, go to the Rome online day trip planner.

Take a train from Pompeii to Rome in 2.5 hours. Alternatively, you can drive; or take a bus. In October in Rome, expect temperatures between 73°F during the day and 55°F at night. Finish your sightseeing early on the 7th (Sat) so you can drive to Assisi.
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Historic Sites · Tours · Museums · Wineries
Side Trips
Find places to stay Oct 2 — 7:

Assisi — 2 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Kick off your visit on the 8th (Sun): learn about winemaking at Azienda Agraria Saio, pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, take in the architecture and atmosphere at San Damiano, then steep yourself in history at Eremo delle Carceri, and finally step into the grandiose world of Rocca Maggiore. Get ready for a full day of sightseeing on the 9th (Mon): do a tasting at Castello Monte Vibiano Vecchio, then get a dose of the wild on Wild Foods Italy, then examine the collection at Museo della Porziuncola, and finally learn about winemaking at Tili Vini Societa Agricola.

For more things to do, ratings, and more tourist information, use the Assisi trip builder website.

You can drive from Rome to Assisi in 2.5 hours. Other options are to take a train; or take a bus. In October, daily temperatures in Assisi can reach 70°F, while at night they dip to 51°F. Finish your sightseeing early on the 9th (Mon) so you can drive to Siena.
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Wineries · Historic Sites · Wildlife · Outdoors
Side Trips
Find places to stay Oct 7 — 9:

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.
Venture out of the city with trips to Fattoria Casa Sola (in Barberino Val d'Elsa) and Guardastelle Vineyard (in San Gimignano). There's still lots to do: savor the flavors at Food & Drink, gain insight at Scuola di Cucina di Lella, don't miss a visit to Piazza del Campo, and contemplate in the serene atmosphere at San Francesco.

You can plan Siena trip in no time by asking Inspirock to help create your itinerary.

Traveling by car from Assisi to Siena takes 2 hours. Alternatively, you can take a bus; or take a train. In October in Siena, expect temperatures between 73°F during the day and 56°F at night. Wrap up your sightseeing on the 12th (Thu) early enough to drive to Florence.
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Wineries · Historic Sites · Tours · Museums
Side Trips
Find places to stay Oct 9 — 12:

Florence — 5 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Venture out of the city with trips to Castello del Trebbio (in Santa Brigida) and Leaning Tower of Pisa (in Pisa). And it doesn't end there: admire the masterpieces at Florence Academy of Fine Arts, steep yourself in history at Basilica of Santa Croce, see the interesting displays at Pitti Palace, and indulge your senses at Scenic wine tours in Tuscany.

For where to stay, reviews, ratings, and other tourist information, use the Florence itinerary planner.

Getting from Siena to Florence by car takes about 1.5 hours. Other options: take a bus; or take a train. In October, daily temperatures in Florence can reach 71°F, while at night they dip to 54°F. Wrap up your sightseeing by early afternoon on the 17th (Tue) to allow time for the flight back home.
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Historic Sites · Wineries · Tours · Museums
Side Trips
Find places to stay Oct 12 — 17:

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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