Italy Travel Itinerary
+ Top Attractions (By Train)

Milan is the second largest city in Italy, located in the north just below the Italian Alps and Italy's Lake Como and Lake Maggiore. This city is also an important global hub of the fashion industry.

Milan contains many incredible historic buildings and churches, the most iconic being the stunning 14th century Milan Duomo Cathedral in the city center, which is the third largest cathedral in the world and showcases astonishingly complex gothic architecture.

Adjacent to the cathedral you'll find the opulent neoclassical Royal Palace of Milan, as well as the ultra-lavish Galleria Vittorio Emanuele II, a breathtaking 19th century arcade-style shopping mall. Other fashion destinations nearby include the glamorous La Rinascente department store and the boutique-lined Via Montenapoleone shopping street.

Within Milan's vast Sempione Park you can admire the colossal 15th century Sforzesco Castle, which houses several museums, most notably the Civic Collection of Ancient Art and The Museum of Rondanini which houses Michelangelo's last sculpture. On the other side of the park is the Arco della Pace, which bears a striking resemblance to the Arc du Triomphe in Paris.

Northern Italy's Lake Como is extremely scenic and lined with small towns and villages along the mountainous coastlines. The main towns and villages of Lake Como are accessible from Como and Lecco via bus or ferry.

Como is the largest city on the lake and located just north of Milan. Como's historic center is entered through the Porta Terre, a medieval gate tower. Within the old town you'll find the beautiful gothic Como Cathedral and the romanesque Chiesa di San Fedele church. From Como you can take the funicular rail up to the village of Brunate and hike up to Volta's Lighthouse, from which you can enjoy breathtaking panoramic views over Lake Como.

The city of Como also hosts two decadent structures along the lakeshore, including the neoclassical Tempio Voltiano museum with its stately marble interior, as well as the elegant Villa Olmo, a luxurious 18th century villa.

The picturesque city of Venice features stunning and rustic Venetian architecture set amongst countless canals and public squares. Be sure to wander the canals and streets while you're in Venice to enjoy the brilliant architecture of the magnificent city.

The wide Canal Grande winds through the city and is lined with many historic lovely structures. Only a few bridges span the Canal Grande, including the Scalzi Bridge near the train station, and the iconic Rialto Bridge, which leads to the Piazza San Marco (St. Mark's Square).

Italy's capital city is also known as the eternal city as it contains many well-preserved ancient structures alongside medieval, Renaissance, and modern buildings.

Rome's most famous sight is the ancient Roman Colosseum, a strikingly well-preserved amphitheater that's over 2,000 years old and quite large. Be sure to visit the Colosseum in the day, but also see the structure at night when it lights up. Adjacent to the Colosseum is the imposing Arch of Constantine, as well as the entrance to the massive Roman Forum area.

The Roman Forum contains countless ancient structures from different time periods including ancient temples, palaces, squares, government buildings, and much more spread out over a massive area. The entire Forum is incredibly stunning, and would take many hours to fully explore and enjoy.

Across from the Roman Forum are the ancient remains of the Trajan Forum and Trajan's Market which sit just below the streets with balconies providing views over the ruins. Both the Roman and Trajan Forum are open for night tours when the ancient structures are majestically lit up.

There's a saying that while Rome may be the heart of Italy, Naples is the soul. The city holds much beauty and is located near many ancient Roman ruins such as Pompeii and Herculaneum, as well as the Amafli coast and the island of Capri (which can be reached by ferry from Naples).

Near the coast you'll find the grandiose Royal Palace of Naples, which lies on the impressive Piazza del Plebiscito across from the monumental San Francesco di Paoloa Basilica, a giant domed church with Greek-style columns and magnificent stunning interiors. The Royal Palace of Naples contains incredibly lavish royal apartments filled with historic furnishings.

Adjacent to the palace is the stately 18th century San Carlo Theatre, as well as the elegant Galleria Umberto I, a stunning glass-domed mall similar to the famous Galleria in Milan. Also nearby you can visit the majestic Zevallos Stigliano Palace.

The ancient Roman city of Pompeii is definitely the most popular archaeological site around Naples, but definitely not the only one. This vast ancient Roman city was buried in ash nearly 2,000 years ago following the eruption of the nearby Mt. Vesuvius. As a result, many of the structures of ancient Pompeii have been quite well-preserved including theatre, stadiums, monuments, and countless houses and villas that you could explore for multiple days.

Nearby Pompeii are the very well-preserved ruins of Villa Oplontis, an elegant villa used by the wife of Emperor Nero.

The picturesque island of Capri is located just off the coast of the Amalfi Coast and is only accessible via ferry from Naples, Sorrento, or Amafli. This tiny island can be easily explored on foot, although it is also recommended to explore Capri's coastline with a boat tour, to see sights such as the Faraglioni sea arch and the vibrant blue Grotta Azzurra sea cave. Additional sea caves include the Grotta Verde and Grotta Bianca (Green and White Caves).

Capri's ferry arrives in Marina Grande, a gorgeous port which sits below the island's mountains. From Marina Grande you can walk up to the Piazetta main square which hosts many restaurants and shops, along with fantastic coastal views.

Near Piazzetta you can visit the Giardini di Augusto, a beautiful clifftop botanical garden with views overlooking the Fraglioni sea arch. From the garden you can hike down to the stunning Marina Piccola Beach or hike up to the Belvedere Tragara viewpoint, which overlooks Marina Piccola from high above.

Sorrento is known for its stunning marinas, which sit below sheer cliffs topped with elegant buildings. The cliffs are best admired from the town's ferry terminal as well as the Spiaggia Sorento beach of Marina Grande. The town also hosts the lovely Cathedral of Sorrento with its ornate interiors, as well as the Vallone dei Mulini, a valley gorge containing the ruins of an ancient mill covered in lush green plants. From town you can hike to a natural ocean pool, the striking Regina Giovanna Bath.

Positano is famous for its gorgeous beaches which sit below the many colorful houses built onto the sides of the mountains. Both the Positano Spiaggia and Fornillo Beaches are excellent places to swim and enjoy the best views of the town.

Florence is the capital of Italy's Tuscany region and is considered the birthplace of the Renaissance. Within the city's historic center you'll find many rustic Renaissance-style buildings and plazas, the most popular square being the Piazza del Duomo. This square hosts the magnificent 13th century Duomo Cathedral, the Giotto's Bell Tower which you can climb for stunning views over the city, and the lavish and intricately decorated Baptistery of St. John.

The Museum of Opera houses all of the art works from the Duomo Cathedral including statues by Michelangelo. It's also possible to climb up to the cathedral's Brunelleschi Dome for more fantastic views.

The city of Pisa is a must-see quick stop for any trip to Italy, located west of Florence and southeast of Cinque Terre. Pisa's most popular attraction is the iconic Leaning Tower of Pisa, an elegant and ornate bell tower which sits on the city's Piazza del Duomo, plaza adjacent to the gorgeous romanesque Pisa Cathedral.

The piazza also hosts the lovely medieval Pisa Baptistery, a striking round domed structure. Be sure to climb to the top of the Leaning Tower to enjoy amazing views over the piazza, cathedral, and sections of the medieval walls that surround the city. Other notable attractions in Pisa are located along the Arno River, including the Blu Palace and the Church of Santa Maria della Spina.

Cinque Terre consists of five picturesque towns/villages along the coast which are surrounded by steep mountains and cliffs along the Italian Riviera. These idyllic towns are among the most beautiful places in the world, and are all connected and reached within minutes via a fast and efficient train which also connects to Sestri Levante to the northwest and La Spezia to the southeast.

The five villages of Cinque Terre from northwest to southeast are Monterosso al Mare (the largest town), Vernazza, Corniglia, Manarola, and Riomaggiore. Also frequently visited with Cinque Terre is the beautiful town of Portovenere, located just southeast of the villages on the tip of a peninsula.

If you'd like to experience the towns of Cinque Terre from a different perspective (and in a short amount of time), consider taking a boat tour along the coast to admire these gorgeous villages from the ocean.

The best way to experience the Cinque Terre coast is to hike along the Sentiero Azzuro Trail, which connects the five towns and features stunning coastal views along the way. This trail and others require a permit to hike along (which can be easily and cheaply purchased online) and can be combined with train rides between the villages. Another amazing trail is the High Trail which travels high up in the mountains above the Cinque Terre villages, offering breathtaking views over the coastline and towns.