36 days in Italy Itinerary

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.

You'll find plenty of places to visit near Milan: Tremezzina (Villa del Balbianello & Villa Carlotta), Bellagio (I Giardini di Villa Melzi & Kayaking & Canoeing) and Greenway del Lago di Como (in Colonno). There's much more to do: contemplate in the serene atmosphere at Duomo di Milano, take an in-depth tour of Pinacoteca Ambrosiana, admire the landmark architecture of Galleria Vittorio Emanuele II, and test your team's savvy at 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.

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), Modena (Acetaia Giuseppe Giusti & Acetaia Villa San Donnino) and Basilica di Sant'Andrea di Mantova (in Mantua). And it doesn't end there: catch a live performance at Arena di Verona, hunt for treasures at Piazza delle Erbe, contemplate in the serene atmosphere at Basilica di San Zeno Maggiore, and contemplate the waterfront views at Lago di Garda.

To find other places to visit, photos, ratings, and other tourist information, go to the Verona road trip website.

Traveling by car from Milan to Verona takes 2 hours. Alternatively, you can take a train. In September, daily temperatures in Verona can reach 78°F, while at night they dip to 58°F. Finish your sightseeing early on the 28th (Wed) to allow enough time to drive to Venice.

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.

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: Amalfi (Museo della Carta, Duomo di Sant'Andrea, &more), Sorrento (Cattedrale di Sorrento, Food Tours, &more) and Ravello (Convento Frati Minori Conventuali S.Francesco, Villa Rufolo, &more). There's much more to do: take a memorable drive along Amalfi Coast, kick back and relax at Fornillo, stroll through Lido Capo di Conca, and take in the architecture and atmosphere at Chiesa di Santa Croce.

To find ratings, traveler tips, more things to do, and tourist information, read Positano driving holiday planning app.

You can fly from Venice to Positano in 3 hours. Other options are to drive; or do a combination of train and bus. Traveling from Venice in October, things will get somewhat warmer in Positano: highs are around 72°F and lows about 63°F. Cap off your sightseeing on the 7th (Fri) early enough to go by car to Pompeii.

Pompeii has been a tourist destination for more than 250 years.

You'll find plenty of places to visit near Pompeii: Ravello (Kundry Bottega d'Arte, Duomo di Ravello, &more), Societa Agricola Tenuta San Francesco - S.R.L. (in Tramonti) and Speed Boats Tours (in Salerno). 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.

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.

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.

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. And it doesn't end there: savor the flavors at Food & Drink, take in the spiritual surroundings of San Francesco, deepen your understanding at Scuola di Cucina di Lella, and let your taste buds guide you at a local gastronomic tour.

To find where to stay, traveler tips, ratings, and other tourist information, read Siena online trip builder.

Traveling by car from Assisi to Siena takes 2 hours. Alternatively, you can take a bus; or take a train. In October, plan for daily highs up to 73°F, and evening lows to 56°F. Finish your sightseeing early on the 21st (Fri) to allow enough time to drive to Florence.

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: Castello del Trebbio (in Santa Brigida) and Leaning Tower of Pisa (in Pisa). 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.