I love walking in Milan--I do it every day, weather permitting (and it usually does, as long as you bring an umbrella and have appropriate shoes).
Top Walking Routes
A couple of notes--these are continuous routes, more-or-less straight, but changing names frequently. These are not the main thoroughfares of cars; on most of these roads, cars are limited or blocked from using them, or they are one-way streets which it is difficult to enter. Obviously, since we're talking walking, you can go the other way from what I have here (I had to pick a direction), reversing the side of the turns and the landmarks.
Milan has installed a number of new neighborhood maps at key intersections in the popular areas, which should help a lot. It can be quite difficult to navigate, even with GPS apps. There isn't that much danger if one makes a wrong turn, though; the tough part will be to decide whether to continue on to unknown parts, or turn around and go back to the last known landmark.
1) Piazza Castello to Piazza San Babila. Via Dante/Via Orefici/Piazza Duomo/Corso Vittorio Emmanuele II. This one has to be listed first, not that it is the best route of all, but it's a good starting point, hitting several of the high points and linking up with the other routes. This one describes a rough East-West arc across the center of the inner ring, beginning at the Castello Sforzesco (the in-town temporary Expo pavilion can be the starting point), heading southeast along wide pedestrian-only Via Dante. At Piazza Cordusio, either veer right to stay on Via Dante or veer left to Via dei Mercanti--each brings you into the impressive Piazza Duomo, which you cross along its length, staying to the left of the Cathedral (unless, of course, you want to go in). On the right is Palazzo Reale, on the left the famous Galleria Vittorio Emmanuele II (more about both in Pt. 2). Leaving Piazza Duomo to the northwest (left of the Cathedral), you go along Corso Vittorio Emmanuele II, like Via Dante wide and pedestrian only. Depending on the daty of the week, time of day, and the weather, this whole route could be packed with people and street performers, or it could be totally deserted. In any case, it is surely lined with commercial establishments, particularly the less-elegant clothing stores, restaurants catering to tourists, and (in the Piazza Duomo and the Galeria V.E. II), major department stores and book/music stores. .
2) Piazza Della Scala to Porta Nuova. Via Verdi/via Brera/via Solferino. This route goes South to North, through the top half of the inner two rings. From the Duomo, pass straight through the Galleria V.E II under its great arched Victorian roof.--you may have to wade through sizable crowds--exiting into a large square with a fountain and a statue of Leonardo (usually with some street musician; the acoustics are good there). On the opposite side of this Piazza is the front entrance to the La Scala opera house. Cross the busy cross-street and pass La Scala on the right to enter via Verdi; after a couple of blocks and some monumental bank offices, the street becomes via Brera, pedestrian-only, broad, quiet, and lined with landmarks buildings and monuments. Via Brera ends at a major East-west thoroughfare (via Pontaccio/via Fatebenefratelli--the edge of the first ring); cross it and continue onto via Solferino. (Just before that intersection is an east-west pedestrian route--via Fiori Chiari to the left/via Fiori Oscuri to the right--with Bar Brera at the corner. This one can be useful at night--the East-West routes are generally more problematic--but it is narrow, crowded and a little too touristy otherwise.) Via Solferino is a fairly long street, with some parts more interesting (nice restaurants) and a fairly long stretch in which you pass the offices of Corriere della Sera, the New York Times of Italy. At the end of the road, where you reach the busy road at the edge of the second ring, is the remains of an old canal, where there is a nice beer hall on the left, and one block to the left (via Milazzo) is the nicest art cinema in town (though I warn you that even there, 90% of the movies will either be Italian or dubbed into Italian).
and Galleria V.Emmanuele II
|pocket park and Hayez statue - via Brera|
3) Stazione Garibaldi to Piazza Cordusio. Corso Como/Corso Garibaldi/via Mercato/via Ponte Vetero/via Broletto. Garibaldi (inner part of the third ring) is the second-most significant train station of general use (routes to the north and northwest, also a major linkage point for the Metro), thus an easy starting point. Corso Como is a fairly short, but busy route, with some limited traffic and a couple of the most popular disco clubs; then you cross the Piazza XXV Aprile (April 25th is the date celebrating the end of WWII in Italy) continuing onto Corso Garibaldi. This street is long, wide with a narrow, limited car lane, and lined on both sides with shops and restaurants in low-rise buildings. It continues through a busy intersection (via della Moscova), after which it only gets nicer. At the next major intersection (it's a bit messy; you have to cross the Tram tracks) the road continues on in the same manner, under the names of via Mercato and then via Ponte Vetero. There is finally a major intersection (cross street is via Cusani to the right, via dell'Orso to the left), at which you can decide: turn right to Castello Sforzesco, turn left toward via Monte di Pieta and the Fashion District (see #4), or straight onto via Broletto. Broletto is a less pleasing street, with a busy tram line in the middle, but it feeds into Piazza Cordusio at its end (see route #1).
At this point, I must mention a key linkage between routes #2 and #3. At via Ancona and via Solferino (if going North), or just past Piazza San Simpliciano on Corso Garibaldi (major church on the left, if going South), you can find my favorite side street. The entrance is called via dello Tessa from Corso Garibaldi (though San Simpliciano also feeds into it beside the church). This interior, pedestrian-only street runs by the seminary and Piazza Paolo VI, and is called via dei Cavalleri del Santo Sepolcro ("Knights of the Holy Sepulchre", doubtlessly a Crusader-era gang). It's only 100m or so in length, but is lined with flowering trees, and beautiful buildings--it's also one without motorized traffic.
4) Stazione Centrale to Piazza San Babila. Via Pisani/Piazza della Repubblica/via Turati/via Principe Amedeo/via Marco dei Marchi/via Giardini/via Montenapoleone. This is a long but rewarding route going roughly North-South down the Northeastern corner of the city center, starting at the principal train station (middle third ring).. Via Pisani, which runs from the station to Piazza della Repubblica, is a busy street, but extremely wide with broad sidewalks and lots of office entrances, sidewalk cafes, etc. You cross Piazza della Repubblica, which is oriented at a right angle to your direction, and I have to say it can be difficult, with lots of cross traffic: better obey the pedestrian street signals in this case. Via Turati is a another busy street but not difficult to walk; at a major cross-street (via della Moscova, at the Piazza Stati Uniti d'America--that's right; the intersection of Moscow and the USA!), bear right (the American consulate will then be on the left). The road gets really nice then, with some of the most beautiful residences in the city center, and a lovely, largely unused park (Giardini Perego) on the right. At via Pisoni (not to be confused with via Pisani), you must decide whether you want the full or partial Armani exposure. If the former, turn at Pisoni, go one block, and turn right on via Manzoni (super-busy street) for one block. You will walk by the entrances of the Hotel Armani. Otherwise, continue one more block on via dei Giardini, turn left at Via Croce Rosso (walking behind the Hotel) and cross Manzoni onto via Montenapoleone.
Via Montenapoleone is probably the most famous street in Milan, it has a lightly-traveled car lane, but it is basically all about the fabulous shop windows of dozens of major fashion houses, on both sides of the street, and other luxury items (Tiffany, Chopard; there are usually a couple of Ferraris or Lamborghinis around; Four Seasons is on a side street to the left, etc.) Take your time and observe Milan's elite out for a stroll or trying to do the high-fashion business. The street is even nicer at night, when it's not so crowded. It will end at the mouth of Piazza San Babila (see #1).
To make it a bit more complicated still, there are a couple of alternatives. At via della Moscova, if you bear to the left of the building with the American consulate, you stay on via Turati. Cross over at some point before the arch and square which you see ahead, at the end (thus avoiding having to cross messy Piazza Cavour). Go under the arch, immediately cross the street, and you will be at the entrance of Via della Spiga, which is like via Montenapoleone, only better. The same line of (different) fabulous fashion shop windows, but a pedestrian-only street (technically, a couple parts allow cars). I give it my highest recommendation. At its end, you take a right on Corso Venezia for a short distance and you get to San Babila. Finally, if walking through all the luxury of via Montenapoleone/via della Spiga offends you, just stay on via Manzoni, and it will take you back to Piazza della Scala (see #1, #2).
(At left, Via della Spiga, at night).
5) Duomo to Porta Ticinese. via Torino/corso di Porta Ticinese. Clearly, this route has the advantage of being a lot simpler than the last one. We move from the elite/bourgeois attractions of the first four routes to the more popular routes of the everyday folks. Exit the Piazza Duomo from its Southwest corner onto via Torino. It's a busy street, with a tram running down the middle, so somewhat difficult to cross. Shops and cafes and street food run continuously on both sides, and there are a number of interesting side streets going off in both directions--just don't get too far off the main drag, though, or you will get lost quickly. Eventually, you arrive at the Corso di Porta Ticinese; turning left, you head due South. It's a fairly normal big city street for awhile, but with parks and churches off to both sides, and plenty of bars in sight. Near the arch of the Porta Ticinese, there's a large square with several more bars. Lots of young people will be found on any evening with reasonable weather or a good soccer game.
6) The Navigli. If Porta Ticinese only whetted your appetite for partying, then continue on through the arch. There is a small lagoon to traverse, bearing to the right, and there will be two different canals heading South and Southwest. Both canals are lined with restaurants and club; the one further to the right (toward the Southwest) is the wider one, Naviglio (Canal) Grande, the other is the Naviglio Pavese (it goes toward the town of Pavia). The Naviglio Grande has to be crossed through one of several pedestrian bridges; there is also a boat which goes up and down the canal when the conditions are right. The water flows fairly well on the canals, but there are some side ditches which tend to breed mosquitoes during the summer. This lively area goes on for quite a while--in distance, and into the night.
7) Via Guastalla/Via della Commenda. Finally (!), a route I discovered recently. It's a quiet, beautiful, straight path in the North-South direction which cuts a great deal of distance off the other routes in the Southeast direction, between the first ring (marked by the Via Larga) and the second (ending at Porta Romana). It basically avoids the interruptions of the roads for the complexes of the old hospital and the Universita degli Studi (though that ancient college complex is also worth a visit). It's mostly pedestrian-only, passing by some beautiful residential buildings, a synagogue (guarded 24 hours a day) and a park (Giardino della Guastalla) which faces on the back of the university complex. There are entrances to the public hospital, the remnants of what appears to be a 19th-century asylum, and the road gives way to shops, restaurants, and a high school on via della Commenda. At the road's South end (via Orti), turn right for a short distance and turn left on Corso di Porta Romana, if the Porta (which has some old Spanish walls and a Roman ceremonial arch at the center of the square, along with a refurbished old spa) is your destination.
The only trick is finding the beginning of via Guastalla on its North end. From the Duomo or Corso VE II, go South, passing through Piazza Fontana, and continuing on until Via Larga (the "Wide Road"--probably was once a canal, I imagine), turning left onto Verzieres, then onto Largo Augusto, staying to the right. You need to cross a wide street (via Francesco Sforza to the right/via Uberto Visconti di Modrone to the left) , which leads to the beginning of a wide avenue, the Corso di Porta Vittoria--looking down that wide avenue, you can see a large pedestal and statue at its end. Instead, go one short block, in front of an old building (the Biblioteca Comunale, or public library), and turn right on the dark, empty street. That is via Guastalla--at most you will see a pedestrian or two coming out of it, as it's practically impossible to enter the last stretch of the road by car. And then you can breathe easier, walking relaxedly and safely.