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.

Explore Milan's surroundings by going to Cathedral of Como (Duomo) (in Como), Tremezzina (Villa del Balbianello & Villa Carlotta) and Bellagio (I Giardini di Villa Melzi & Kayaking & Canoeing). The adventure continues: contemplate in the serene atmosphere at Duomo di Milano, pause for some serene contemplation at Chiesa di San Maurizio al Monastero Maggiore, test your problem-solving skills at La Casa Maledetta, and explore the world behind art at Pinacoteca Ambrosiana.

To see photos, where to stay, more things to do, and other tourist information, refer to the Milan online driving holiday planner.

Tampa, USA to Milan is an approximately 15-hour flight. The time zone difference moving from Eastern Standard Time to Central European Standard Time is 6 hours. Expect slightly colder temperatures when traveling from Tampa in September; daily highs in Milan reach 76°F and lows reach 57°F. Wrap up your sightseeing on the 16th (Sat) early enough to drive 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 a short trip to Gardaland Park in Castelnuovo del Garda (about 32 minutes away). There's much more to do: catch a live performance at Arena di Verona, step into the grandiose world of Piazzale Castel San Pietro, explore the activities along Lago di Garda, and take in panoramic vistas at Torre dei Lamberti.

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.

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: Toni Doro - Il Prosecco (in Vittorio Veneto), Scrovegni Chapel (in Padua) and PDC Cartizze (in Valdobbiadene). 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.

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.

Venture out of the city with trips to Torre del Capo di Conca (in Conca dei Marini), Amalfi (Valle delle Ferriere, Fontana sant'Andrea, &more) and Ravello (Ceramiche Cosmolena di Margherita di Palma, Villa Rufolo, &more). The adventure continues: indulge in some culinary diversions at a local gastronomic tour, take in the architecture and atmosphere at Cattedrale di Sorrento, surround yourself with nature on I Suoni degli Dei - Pelagos, and take a memorable drive along Amalfi Coast.

To see photos, other places to visit, maps, and more tourist information, read Positano trip planner.

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, you can expect nighttime temperatures to be somewhat warmer in Positano, with lows of 68°F. Finish your sightseeing early on the 28th (Thu) to allow enough time to drive to Pompeii.

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), Ravello (Ravello Arte, Kundry Bottega d'Arte, &more) and Salerno (Promenade Trieste, Duomo di Salerno, &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.

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.

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.

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.

Explore the numerous day-trip ideas around Siena: Guardastelle Vineyard (in San Gimignano) and Fattoria Casa Sola (in Barberino Val d'Elsa). There's still lots to do: indulge your senses at some of the top wineries in the area, 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.

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, take in panoramic vistas at Campanile di Giotto, and don't miss a visit to Piazzale Michelangelo.

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.