31 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.

On the 2nd (Tue), explore the world behind art at Pinacoteca di Brera, explore the different monuments and memorials at Monumental Cemetery, and then admire the masterpieces at Pinacoteca Ambrosiana. Get ready for a full day of sightseeing on the 3rd (Wed): admire the striking features of Galleria Vittorio Emanuele II, then pause for some serene contemplation at Basilica San Lorenzo Maggiore, then take in the architecture and atmosphere at Duomo di Milano, and finally explore the historical opulence of Castello Sforzesco.

To see maps, ratings, photos, and other tourist information, refer to the Milan tour itinerary builder site.

New York City, USA to Milan is an approximately 12-hour flight. Due to the time zone difference, you'll lose 6 hours traveling from New York City to Milan. In May, plan for daily highs up to 73°F, and evening lows to 55°F. Wrap up your sightseeing on the 3rd (Wed) 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.

Explore Florence's surroundings by going to Pisa (Museo Aviotruppe Esercito Italiano & Leaning Tower of Pisa) and St Martin Cathedral (in Lucca). Next up on the itinerary: admire the masterpieces at Florence Academy of Fine Arts, pause for some serene contemplation at Basilica of Santa Croce, don't miss a visit to Piazzale Michelangelo, and get a sense of history and politics at Palazzo Vecchio.

To plan Florence vacation without wasting time, ask Inspirock to design an itinerary.

Traveling by train from Milan to Florence takes 2.5 hours. Alternatively, you can drive; or take a bus. May in Florence sees daily highs of 71°F and lows of 52°F at night. Finish your sightseeing early on the 8th (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.

Change things up with these side-trips from Siena: Guardastelle Vineyard (in San Gimignano), Buccelletti - Cantina (in Castiglion Fiorentino) and Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate). The adventure continues: indulge your senses at some of the top wineries in the area, take in the spiritual surroundings of San Francesco, don't miss a visit to Centro Storico di Siena, and take in the architecture and atmosphere at Duomo di Siena.

For maps, where to stay, reviews, and more tourist information, use the Siena road trip tool.

Getting from Florence to Siena by car takes about 1.5 hours. Other options: take a bus; or take a train. Expect a daytime high around 74°F in May, and nighttime lows around 53°F. Finish up your sightseeing early on the 12th (Fri) so you can go by car to Assisi.

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

Change things up with these side-trips from Assisi: Montioni Frantoio e Cantina (in Montefalco) and Vineria del Carmine (in La Bruna). There's much more to do: pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, do a tasting at Tili Vini Societa Agricola, explore the historical opulence of Rocca Maggiore, and contemplate in the serene atmosphere at Eremo delle Carceri.

For photos, other places to visit, traveler tips, and tourist information, you can read our Assisi travel route builder.

Drive from Siena to Assisi in 2 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 72°F in May, and nighttime lows around 52°F. Finish your sightseeing early on the 15th (Mon) 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.

Step out of Rome to go to Tivoli and see Villa Adriana, which is approximately 36 minutes away. There's lots more to do: delve into the distant past at Pantheon, appreciate the extensive heritage of Piazza Navona, steep yourself in history at Colosseum, and explore the world behind art at Galleria Borghese.

For maps, where to stay, other places to visit, and more tourist information, read our Rome journey planner.

Drive from Assisi to Rome in 2.5 hours. Alternatively, you can take a train; or take a bus. Traveling from Assisi in May, expect a bit warmer with lows of 58°F in Rome. Finish your sightseeing early on the 20th (Sat) to allow enough time to take a train to Naples.

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Explore the numerous day-trip ideas around Naples: Pompeii (Lupanar & Tempio di Giove Capitolino) and Food Tours (in Sorrento). There's lots more to do: explore the ancient world of Pompeii Archaeological Park, pause for some serene contemplation at Cloister of Santa Chiara, explore the world behind art at Museo e Real Bosco di Capodimonte, and see the interesting displays at Museo Archeologico Nazionale di Napoli.

For where to stay, traveler tips, reviews, and other tourist information, use the Naples trip planner.

Traveling by train from Rome to Naples takes 2 hours. Alternatively, you can drive; or fly. In May in Naples, expect temperatures between 74°F during the day and 58°F at night. Wrap up your sightseeing on the 23rd (Tue) early enough to drive to Amalfi.

Known for its impressive hillside cascade of colorful stone buildings down to the Mediterranean shore, Amalfi is the cultural and commercial heart of southern Italy's Amalfi Coast.

Explore the numerous day-trip ideas around Amalfi: Positano (Il Sentiero Degli Dei, Boat Tours & Water Sports, &more). Next up on the itinerary: take in nature's colorful creations at Villa Cimbrone Gardens, take in the spiritual surroundings of Duomo di Sant'Andrea, Head underground at Cave of Smeraldo, and examine the collection at Museo della Carta.

To see reviews, traveler tips, other places to visit, and other tourist information, go to the Amalfi trip planner.

You can drive from Naples to Amalfi in 1.5 hours. Other options are to take a bus; or do a combination of train and bus. Expect a bit warmer evenings in Amalfi when traveling from Naples in May, with lows around 65°F. Finish your sightseeing early on the 27th (Sat) to allow enough 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.

Venture out of the city with trips to Verona (Casa di Giulietta, Arena di Verona, &more). And it doesn't end there: explore the activities along Canal Grande, take in the architecture and atmosphere at San Giorgio Maggiore, snap pictures at Ponte di Rialto, and admire the masterpieces at Peggy Guggenheim Collection.

To see photos, ratings, and more tourist information, refer to the Venice route builder app.

Fly from Amalfi to Venice in 3 hours. Alternatively, you can do a combination of taxi and train; or drive. Expect little chillier evenings in Venice when traveling from Amalfi in May, with lows around 55°F. Wrap up your sightseeing on the 31st (Wed) to allow time to fly back home.