Milan isn’t a cruise port — but it is one of the smartest cities to add before or after your Mediterranean sailing. With Italy’s high‑speed trains connecting Milan to Venice, Florence, and Rome, it’s incredibly easy to turn your cruise into a full Italian vacation.

Many travelers fly into Milan because it often has better flight options and pricing. That’s exactly what we did: we flew into Milan, explored the city, then took the train to Venice, Florence, and finally Rome to catch our cruise. It was the perfect pre‑cruise itinerary — relaxed, efficient, and a great way to see more of Italy without adding complicated travel days.

If you’re looking to maximize your time in Italy before or after your cruise, Milan is a stylish, modern, and surprisingly easy place to start.

Top Things to Do in Milan, Italy

1. Duomo di Milano (Milan Cathedral)

This massive Gothic cathedral is the heart of Milan and one of the most recognizable landmarks in Italy. Its intricate façade and soaring interior make it a must‑see for first‑time visitors. For more details about visiting the Milan Cathedral, check out my detailed Duomo di Milano blog post.

2. Duomo Rooftop Terraces

Walking along the rooftop terraces lets you get up close to the cathedral’s famous spires and enjoy sweeping views of the city. It’s one of the most unique photo spots in Milan. For more details about exploring the Duomo Rooftop Terraces, check out my detailed rooftop guide.

3. Galleria Vittorio Emanuele II

This elegant 19th‑century shopping arcade is perfect for browsing, people‑watching, and grabbing a cappuccino under its glass dome. It’s also one of the most photographed spots in Milan. For more details about the Galleria Vittorio Emanuele II, check out my detailed Galleria guide.

4. Teatro alla Scala

La Scala is one of the world’s most prestigious opera houses, offering tours and unforgettable performances. Even if you’re not an opera fan, the history and architecture are worth the visit. For more details about Teatro alla Scala, check out my detailed La Scala blog post.

5. Sforza Castle (Castello Sforzesco)

This impressive fortress houses multiple museums and beautiful courtyards you can explore at your own pace. It’s a great place to combine history, art, and a relaxing stroll. For more details about Sforza Castle, check out my detailed Castello Sforzesco blog post.

6. Santa Maria delle Grazie (The Last Supper)

Home to Leonardo da Vinci’s iconic mural, this UNESCO site requires advance reservations due to limited viewing times. Seeing The Last Supper in person is truly unforgettable. For more details about seeing The Last Supper, check out my detailed Santa Maria delle Grazie blog post.

7. Brera District

Brera is Milan’s artsy neighborhood, filled with boutiques, cafés, and charming cobblestone streets. It’s the perfect place to wander and soak up the city’s creative energy. For more details about exploring the Brera District, check out my detailed Brera blog post.

8. Navigli Canals

This lively canal district comes alive in the evenings with restaurants, bars, and sunset views. It’s one of the best places in Milan to enjoy aperitivo. For more details about the Navigli Canals, check out my detailed Navigli blog post.

9. Porta Nuova District

Milan’s modern skyline shines in this futuristic neighborhood filled with sleek architecture and trendy spots. It’s a fun contrast to the city’s historic center. For more details about the Porta Nuova District, check out my detailed Porta Nuova blog post.

10. San Siro Stadium

Sports fans will love touring the home stadium of AC Milan and Inter Milan. Even non‑fans appreciate the scale and energy of this iconic venue. For more details about visiting San Siro Stadium, check out my detailed San Siro blog post.

11. Quadrilatero della Moda (Fashion District)

This luxury shopping district showcases Milan’s fashion identity with designer boutiques and stylish window displays. It’s a great place to browse or simply admire the glamour. For more details about the Fashion District, check out my detailed Quadrilatero della Moda blog post.

12. Pinacoteca Ambrosiana

This historic art museum features masterpieces by Caravaggio, Raphael, and Leonardo da Vinci. It’s a quieter, more intimate alternative to Milan’s larger museums. For more details about the Pinacoteca Ambrosiana, check out my detailed Ambrosiana blog post.

13. Parco Sempione

Located behind Sforza Castle, this large park is perfect for a relaxing break between sightseeing stops. It’s also a great spot for photos and people‑watching. For more details about Parco Sempione, check out my detailed Parco Sempione blog post.

14. La Rinascente Rooftop

This department store rooftop offers great views of the Duomo along with several dining options. It’s a perfect place to unwind after exploring the city center. For more details about the La Rinascente Rooftop, check out my detailed rooftop dining blog post.

15. Corso Como

This trendy pedestrian street is known for its boutiques, cafés, and nightlife. It’s a stylish area to explore in the afternoon or evening. For more details about Corso Como, check out my detailed Corso Como blog post.

16. Monumental Cemetery

More like an open‑air art museum, this cemetery is filled with elaborate sculptures and stunning architecture. It’s peaceful, unique, and surprisingly beautiful. For more details about the Monumental Cemetery, check out my detailed Monumental Cemetery blog post.

17. Piazza Mercanti

Tucked behind the Duomo, this medieval square offers a quieter, atmospheric escape from the crowds. It’s a great place to appreciate Milan’s older architecture. For more details about Piazza Mercanti, check out my detailed Piazza Mercanti blog post.

18. Milan’s Aperitivo Culture

Aperitivo is a beloved Milan tradition — a pre‑dinner drink paired with small bites. It’s one of the best ways to experience local life. For more details about enjoying aperitivo in Milan, check out my detailed aperitivo guide.

19. Day Trip to Lake Como

Just 40 minutes by train, Lake Como offers stunning scenery, charming towns, and relaxing lakeside views. It’s an easy and unforgettable escape from the city. For more details about a Lake Como day trip, check out my detailed Lake Como blog post.https://cruisingtosunshine.com/day-trip-to-lake-como/

20. Day Trip to Bergamo

This hilltop town features medieval streets, panoramic views, and a charming old‑world feel. It’s a great half‑day or full‑day trip from Milan. For more details about visiting Bergamo, check out my detailed Bergamo blog post.