29 days in Italy Itinerary

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.

Kick off your visit on the 13th (Thu): take in nature's colorful creations at Giardino Giusti, then snap pictures at Ponte Scaligero, and then pause for some serene contemplation at Basilica di Santa Anastasia. On the 14th (Fri), you'll have a packed day of sightseeing: catch a live performance at Arena di Verona, wander the streets of Piazza delle Erbe, take in panoramic vistas at Torre dei Lamberti, examine the collection at Casa di Giulietta, then take in the spiritual surroundings of Basilica di San Zeno Maggiore, and finally explore the historical opulence of Museo di Castelvecchio.

For photos, maps, where to stay, and more tourist information, read Verona journey app.

Chicago, USA to Verona is an approximately 13.5-hour flight. You'll lose 7 hours traveling from Chicago to Verona due to the time zone difference. In July, daytime highs in Verona are 88°F, while nighttime lows are 66°F. Wrap up your sightseeing on the 14th (Fri) early enough to drive to Milan.

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 15th (Sat): make a trip to Galleria Vittorio Emanuele II, contemplate in the serene atmosphere at Duomo di Milano, and then stroll the grounds of Monumental Cemetery.

Planning Milan trip won't be overwhelming when you use Inspirock's itinerary maker.

Traveling by car from Verona to Milan takes 2 hours. Alternatively, you can take a train. In July, plan for daily highs up to 85°F, and evening lows to 65°F. Wrap up your sightseeing on the 15th (Sat) to allow time to take a train to Florence.

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.

Change things up with these side-trips from Florence: Leaning Tower of Pisa (in Pisa) and Siena (Piazza del Campo & Wine Tours & Tastings). Next up on the itinerary: explore the world behind art at Florence Academy of Fine Arts, get a sense of history and politics at Palazzo Vecchio, see the interesting displays at Pitti Palace, and contemplate in the serene atmosphere at The Baptistery of St. John.

For photos, traveler tips, maps, and other tourist information, use the Florence trip builder app.

Traveling by train from Milan to Florence takes 2.5 hours. Alternatively, you can drive; or take a bus. In July, daily temperatures in Florence can reach 86°F, while at night they dip to 65°F. Finish your sightseeing early on the 20th (Thu) so you can drive to Assisi.

Rich in culture and religious tradition, Assisi is known as the birthplace of St.

On the 21st (Fri), do a tasting at Azienda Agraria Saio, then pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, then see the interesting displays at Museo della Porziuncola, and finally do a tasting at Tili Vini Societa Agricola. Here are some ideas for day two: explore the world behind art at Collegio del Cambio, surround yourself with nature on Wild Foods Italy, then stop by Assisi Jewels, then pause for some serene contemplation at San Damiano, and finally contemplate the long history of Eremo delle Carceri.

For ratings, more things to do, traveler tips, and other tourist information, use the Assisi travel planner.

You can drive from Florence to Assisi in 2.5 hours. Alternatively, you can take a train. Expect a daytime high around 89°F in July, and nighttime lows around 64°F. Finish your sightseeing early on the 22nd (Sat) so you can drive to Rome.

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, sightseeing, and nightlife. Your trip includes some of its best attractions: take in the architecture and atmosphere at St. Peter's Basilica, delve into the distant past at Colosseum, admire the masterpieces at Vatican Museums, and steep yourself in history at Roman Forum.

For photos, traveler tips, where to stay, and other tourist information, go to the Rome online itinerary planner.

Getting from Assisi to Rome by car takes about 2.5 hours. Other options: take a train; or take a bus. Traveling from Assisi in July, expect a bit warmer with lows of 70°F in Rome. Cap off your sightseeing on the 27th (Thu) early enough to go by car to Salerno.

While often overshadowed by the Amalfi Coast's array of quaint villages, Salerno has become one of the region's main areas for culture and entertainment, while remaining relatively unmarked by tourism.

Venture out of the city with trips to Paestum (Parrocchia Ss. Annunziata & Archaeological Park of Paestum). On the 29th (Sat), spend a thrilling day on the water with a speed boat tour. And it doesn't end there: steep yourself in history at Pompeii Archaeological Park, head outdoors with Cilento, take in nature's colorful creations at Giardino della Minerva, and browse for treasures at Libreria Antiquaria Vecchi Libri.

For photos, traveler tips, more things to do, and tourist information, use the Salerno journey maker app.

Drive from Rome to Salerno in 3 hours. Alternatively, you can take a train; or take a bus. When traveling from Rome in July, plan for little chillier days and somewhat warmer nights in Salerno: temperatures range from 84°F by day to 77°F at night. Finish your sightseeing early on the 31st (Mon) to allow enough time to drive 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: Duomo di Sant'Andrea (in Amalfi), Food Tours (in Sorrento) and Ravello (Belvedere Principessa di Piemonte, Villa Rufolo, &more). There's lots more to do: get a new perspective on things with Boat Tours & Water Sports, cruise along Amalfi Coast, stroll through Arienzo Beach Club, Positano, and get great views at Il Sentiero Degli Dei.

For where to stay, other places to visit, ratings, and tourist information, read our Positano trip itinerary maker app.

Getting from Salerno to Positano by car takes about 1.5 hours. Other options: do a combination of train and taxi; or do a combination of bus and ferry. Traveling from Salerno in July, plan for slightly colder nights in Positano, with lows around 72°F. Wrap up your sightseeing on the 5th (Sat) to allow time to fly 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.

Explore the numerous day-trip ideas around Venice: Padua (Basilica of St. Anthony & Scrovegni Chapel). The adventure continues: contemplate the waterfront views at Canal Grande, admire the masterpieces at Peggy Guggenheim Collection, enjoy breathtaking views from St Mark's Campanile, and get the lay of the land with Walking tours.

To find ratings, where to stay, other places to visit, and other tourist information, go to the Venice vacation builder site.

Fly from Positano to Venice in 3 hours. Alternatively, you can drive; or do a combination of bus and train. Plan for a bit cooler nights when traveling from Positano in August since evenings lows in Venice dip to 66°F. Wrap up your sightseeing on the 9th (Wed) early enough to fly back home.