36 days in Italy Itinerary

36 days in Italy Itinerary

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

S M T W T F S
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21
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25
26
27
28
29
30
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10
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Milan — 3 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.
Change things up with these side-trips from Milan: Greenway del Lago di Como (in Colonno), Bellagio (I Giardini di Villa Melzi & Kayaking & Canoeing) and Tremezzina (Villa del Balbianello & Villa Carlotta). There's lots more to do: take in the spiritual surroundings of Duomo di Milano, explore the world behind art at Pinacoteca Ambrosiana, admire the striking features of Galleria Vittorio Emanuele II, and see La Casa Maledetta.

To find photos, reviews, other places to visit, and tourist information, read Milan online travel route planner.

Tampa, USA to Milan is an approximately 15-hour flight. The time zone difference moving from Eastern Standard Time (EST) to Central European Standard Time (CET) is 6 hours. Traveling from Tampa in September, things will get slightly colder in Milan: highs are around 76°F and lows about 57°F. Finish up your sightseeing early on the 24th (Sat) so you can go by car to Verona.
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Museums · Historic Sites · Parks · Outdoors
Side Trips
Find places to stay Sep 21 — 24:

Verona — 4 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.
Change things up with these side-trips from Verona: Gardaland Park (in Castelnuovo del Garda), Basilica di Sant'Andrea di Mantova (in Mantua) and Lago di Garda (in Garda). There's still lots to do: see a show at Arena di Verona, hunt for treasures at Piazza delle Erbe, brush up on your knowledge of spirits at Acetaia Giuseppe Giusti, and explore the historical opulence of Museo di Castelvecchio.

To see traveler tips, where to stay, reviews, and other tourist information, read Verona tour planner.

Drive from Milan to Verona in 2 hours. Alternatively, you can take a train. In September, daytime highs in Verona are 78°F, while nighttime lows are 58°F. Cap off your sightseeing on the 28th (Wed) early enough to go by car to Venice.
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Historic Sites · Shopping · Neighborhoods · Breweries & Distilleries
Side Trips
Find places to stay Sep 24 — 28:

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.
Go for a jaunt from Venice to Padua to see Scrovegni Chapel about 54 minutes away. The adventure continues: contemplate the waterfront views at Canal Grande, see the interesting displays at Doge's Palace, admire the masterpieces at Peggy Guggenheim Collection, and admire the striking features of St Mark's Campanile.

For reviews, traveler tips, maps, and other tourist information, you can read our Venice trip itinerary maker.

Getting from Verona to Venice by car takes about 1.5 hours. Other options: take a shuttle; or take a train. Expect a daytime high around 77°F in September, and nighttime lows around 59°F. Cap off your sightseeing on the 2nd (Sun) early enough to catch the flight to Positano.
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Historic Sites · Museums · Tours · Parks
Side Trip
Find places to stay Sep 28 — Oct 2:

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.
Explore the numerous day-trip ideas around Positano: Ravello (Convento Frati Minori Conventuali S.Francesco, Villa Rufolo, &more), Sorrento (Cattedrale di Sorrento, Food Tours, &more) and Amalfi (Museo della Carta, Duomo di Sant'Andrea, &more). There's lots more to do: cruise along Amalfi Coast, kick back and relax at Fornillo, contemplate in the serene atmosphere at Church of Santa Maria Assunta, and tour the pleasant surroundings at Lido Capo di Conca.

To see ratings, other places to visit, where to stay, and other tourist information, read our Positano holiday builder website.

You can fly from Venice to Positano in 3 hours. Other options are to drive; or do a combination of train and bus. Plan for a bit warmer temperatures traveling from Venice in October, with highs in Positano at 72°F and lows at 63°F. Wrap up your sightseeing on the 7th (Fri) early enough to drive to Pompeii.
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Outdoors · Parks · Historic Sites · Tours
Side Trips
Find places to stay Oct 2 — 7:

Pompeii — 3 nights

Underground City

Pompeii has been a tourist destination for more than 250 years.
You'll find plenty of places to visit near Pompeii: Speed Boats Tours (in Salerno), Societa Agricola Tenuta San Francesco - S.R.L. (in Tramonti) and Ravello (Kundry Bottega d'Arte, Duomo di Ravello, &more). Next up on the itinerary: make a trip to Pompeii Archaeological Park, admire the striking features of Villa dei Misteri, explore the ancient world of Forum, and learn about winemaking at Bosco de Medici Winery.

To see other places to visit, traveler tips, reviews, and more tourist information, refer to the Pompeii day trip planning site.

You can drive from Positano to Pompeii in 1.5 hours. Alternatively, you can take a bus. Traveling from Positano in October, plan for a bit cooler nights in Pompeii, with lows around 58°F. Finish your sightseeing early on the 10th (Mon) to allow enough time to take a train to Rome.
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Outdoors · Transportation · Tours · Historic Sites
Side Trips
Find places to stay Oct 7 — 10:

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.
Venture out of the city with trips to Macchina di Santa Rosa (in Viterbo) and Culture Discovery Vacations - Cooking Classes & Vacations (in Soriano nel Cimino). And it doesn't end there: steep yourself in history at St. Peter's Basilica, explore the ancient world of Colosseum, make a trip to Spanish Steps, and admire the striking features of Pantheon.

To see other places to visit, where to stay, ratings, and more tourist information, use the Rome online sightseeing planner.

You can 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. Cap off your sightseeing on the 15th (Sat) early enough to go by car to Assisi.
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Historic Sites · Tours · Museums · Wineries
Side Trips
Find places to stay Oct 10 — 15:

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 16th (Sun): do a tasting at Azienda Agraria Saio, pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, then pause for some serene contemplation at San Damiano, then contemplate the long history of Eremo delle Carceri, and finally explore the historical opulence of Rocca Maggiore. Get ready for a full day of sightseeing on the 17th (Mon): do a tasting at Castello Monte Vibiano Vecchio, then surround yourself with nature on Wild Foods Italy, then examine the collection at Museo della Porziuncola, and finally learn about winemaking at Tili Vini Societa Agricola.

For photos, traveler tips, ratings, and other tourist information, go to the Assisi online itinerary planner.

You can drive from Rome to Assisi in 2.5 hours. Other options are to take a train; or take a bus. Expect a daytime high around 70°F in October, and nighttime lows around 51°F. Finish up your sightseeing early on the 17th (Mon) so you can go by car to Siena.
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Wineries · Historic Sites · Outdoors · Wildlife
Side Trips
Find places to stay Oct 15 — 17:

Siena — 4 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. On the 21st (Fri), give your taste buds a day to remember with a local gastronomic tour. Next up on the itinerary: indulge your senses at some of the top wineries in the area, explore the world behind art at Pinacoteca Nazionale, deepen your understanding at Scuola di Cucina di Lella, and make a trip to Centro Storico di Siena.

For traveler tips, where to stay, more things to do, and other tourist information, you can read our Siena visit planning app.

Drive from Assisi to Siena in 2 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 73°F in October, and nighttime lows around 56°F. Finish your sightseeing early on the 21st (Fri) so you can drive to Florence.
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Tours · Wineries · Historic Sites · Museums
Side Trip
Find places to stay Oct 17 — 21:

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.
Get out of town with these interesting Florence side-trips: Leaning Tower of Pisa (in Pisa) and Castello del Trebbio (in Santa Brigida). And it doesn't end there: explore the world behind art at Florence Academy of Fine Arts, get to know the fascinating history of Piazza del Duomo, take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, and make a trip to Piazzale Michelangelo.

To find more things to do, other places to visit, traveler tips, and tourist information, you can read our Florence trip itinerary builder site.

Getting from Siena to Florence by car takes about 1.5 hours. Other options: take a bus; or take a train. October in Florence sees daily highs of 71°F and lows of 54°F at night. On the 26th (Wed), wrap the sightseeing up by early afternoon so you can fly back home.
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Historic Sites · Wineries · Tours · Museums
Side Trips
Find places to stay Oct 21 — 26:

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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