After having made several European trips over the years in the company of friends and family, circumstances were such that if I wanted to go to Italy in 2026, I would have to do so alone. Traveling solo is something I do a lot domestically, but it would be a first for me internationally. I knew that I would be spending more for things like lodging and rental cars with no one to split the cost, but, the flip side was that I would be free to set an itinerary as I pleased.

I had seen a little bit of Italy way back in 1985, after I graduated from high school. That whirlwind tour included overnight stays in Venice, Rome, and Florence, along with day trips or stops at Verona, Capri and Pompeii (in one day, from Rome), and Pisa. With that in mind, I decided on a loop of Northern Italy, flying into and out of Milan, with 3 nights in Milan, 3 in Monterosso al Mare, 2 in Siena, 3 in Montepulciano, 2 in Florence, 3 in Bologna, and a final night at the airport. I have pretty much settled on the 3 weekends leading up to Memorial Day as my preferred travel window, and scheduled my departure for Wednesday, May 6, and return for Sunday, May 24.

My flight was booked through American, DFW being my usual departure airport, but, as they do not fly direct to Milan from DFW, I had a connecting flight to JFK outward bound, and through LHR (on a British airways flight for the first leg) on the return. Premium Economy on the transatlantic legs ran about $1900 when I booked in early July.

Most of my ground transportation would be mostly by train, but part of the Tuscany segment would be done by rental car, with pick up and drop off at the Florence airport arranged through AutoEurope for $655.60 over six days (using Avis).

I purchased trip insurance through Travel Guard.

Traveling with a iPhone and iPad, I decided to hedge my bets a bit and get separate eSIM’s for both. For the phone, I used Orange Travel which included a voice and data plan for 30 days of unlimited calls with a European number, and 50GB of data, which was similar to what I had done in France in 2022. This was while keeping my US cell number active for voice and texts through Verizon, which you can do with a dual SIM capable phone. Probably overkill, but it was $47.99, so not bad. What was really overdoing it was getting a data plan for the tablet rather than using my phone as a hotspot. I purchased an 18 day plan from Holafly which included unlimited data but cost €59. That was definitely not the frugal choice, but I knew that I would always have data access one way or another.

Wednesday, May 6. Departure day went rather smoothly. Although the flight from DFW to JFK was a few minutes late pushing back, we made up that time with a very short taxi before takeoff and, consequently, arrived at the gate (after a several minutes delay on the ramp) 15 minutes early, which gave me two hours to connect rather than 1:45, but the best thing about the flight was that the middle seat on my row was not occupied (and it might have been the only empty seat on the plane). On the JFK to MXP flight, I was not able to really fall asleep in the premium economy seat, but I did get some relaxing rest listening to music on my noise canceling ear buds. It was the first time I’d used these on a transatlantic flight, and I think it made a big difference.

Thursday, May 7. My plane arrived at Malpensa shortly after 9:00, and I was prepared for delays with the new EES system, where they have to scan your passport, take your fingerprints, then take your picture, but this went surprisingly smoothly. It took two minutes, with half that time devoted to answering questions. After that, you have to go through the exit gate, where they check you against the photo and fingerprints they just took, but that was smooth sailing. I was able to board the Malpensa express to Cadorna station before 10:00, and was into the center of Milan about 10:40. A short taxi ride later, I was at Hotel Gran Duca di York before 11:00.

Thankfully, they had a room ready, so I was able to check in, shower and change clothes before heading out to lunch at Pasto, a pasta making laboratory just a short walk from the hotel. Enjoyed the caccio e pepe. I skipped desert, knowing I had some gelato in my future, and forced myself to walk around the duomo neighborhood for about an hour before stopping for gelato at Ciaco, on via Spadari. I had passed up on another place that was recommended in a YouTube video when I saw that the other place had the colorful mounds of gelato on display that are indicative of something not made on the premises. I was happy with my choice.

After that, I succumbed to the need to sleep, setting an alarm for three hours. It was very hard to get up, but I managed to rouse myself eventually and get ready for some culture, as I was attending an 8:00 pm concert at La Scala. Michelle Marriotti directed Mendelsohn’s 3rd (Scottish) and Dvorak’s 8th. I purchased a seat in a box back when tickets went on sale, and this was a good move. The floor seats seemed to be mostly locals with subscriptions. In the boxes, only the first two seats had good views. Seats 3 and 4 were OK in the center of the auditorium, but they were stools so that the occupants could see over seats 1 and 2. Seats 5 and 6 were stools of the same height behind 3 and 4, so they basically watched like leering through a window several feet away, having to look over and around the folks in front. The folks in 2, 3 and 4 were locals (the guy in seat two seemed to be a regular, while the girl in the couple using 3 and 4 said it was her first time). A couple of tourists had the seats at the back.


Loved Hotel Gran Duca di York

First jet lagged view of thenduomo

Would, have been a great day for the rooftop tour

World’s finest shopping mall?

The grandest I’ve ever seen

Having a box seat at La Scala was a pinch me moment

Excellent performance

Tagging along for the ride.

I’m in!

Me, too!

What a great start! Pasta, gelato, and La Scala!!! Right up my alley. Looking forward to the rest!

Excellent start! Box seat is certainly a splurge ...

€110 euros buying direct from La Scala when the tickets went on sale. Not cheap, but for what might be a once in a lifetime experience, not that bad. They announce the calendar of performances well in advance, but tickets for a concert don’t go on sale until about 90 days before the event (I think opera tickets might have a little grater lead time, like four months). They go on sale at 11 am Italian time, so if you are ordering these from the US, you have to get up early. And, you do not want to wait until the sale date to get your account set up to buy, as that can be tricky. There is a step in the process where you have to verify your email, but, for some reason, the automated system tends to reject US email addresses, and you have to email La Scala directly to get that approved. So, you definitely want to do a dummy booking, all the way up to payment, in advance of your sale date to make sure everything goes smoothly.

Tickets for an opera are much more expensive,. There are cheap seats available, but those are either way up in the rafters, or restricted views.

i could have seen an opera on Saturday night, but it was a five act Debussy opera that is not familiar to me, so I went with the 2 hour symphony concert on arrival day.

Thanks, twk, for this detailed response. Yep, that's a reasonable price, especially for the once in a lifetime experience in La Scala! I would have preferred the concert over a long-ish Debussy opera, too ;-)

Friday, May 8. I had 9:30 reservations for the English guided tour of Da Vinci’s Last Supper at the Basilica Santa Maria Della Grazie. This ticket was obtained firm the official website, so it was only 15€, but, the trick is you have to buy these as soon as they go on sale, usually in blocks of about three months at a time, so more or less quarterly. May was at the front of one of these blocks, so the tickets did not go on sale until late March, if I recall correctly. You are supposed to arrive 20 minutes before your appointed time, the the guide takes you into a holding room to dehumidify for 15 minutes before your group of about 20 people goes in for 15 minutes in the room with the actual painting. As much trouble as that sounds like, it beats the heck out of trying to see the Mona Lisa at the Louvre. You get plenty of time to inspect the painting in as much detail as you like, and with a little patience, to get any pictures that you like. I could include a bunch of details from the painting in my photos for the day, but I'll just stick to the overview.

I had limited time for lunch, so I opted for a schiaciatta sandwich from All’Antico Vinaio, a chain which started in Florence, but now has even opened a few outlets in the US. I loved the Al Paradiso sandwich (mortadella) so much I had it again later in the trip. The street food scene in Italy should not be overlooked when you are thinking about the food aspect of your Italy trip.

My afternoon activity was seeing the duomo, starting with taking the elevator to the rooftop. I got some bad advice, and was led to believe that I needed to enter the cathedral before getting in the fast track line. This was completely backwards. With the fast track ticket, you go to the back (SE) side of the cathedral and go directly to the elevator, which takes you about 2/3 of the way up. Because of this mix up, I was early, but the attendant let me go on up since there was not a horrendous line, yet. After you do the rooftop, then you get to see the interior without any further standing in line. The interior is huge but rather dark. Not my favorite cathedral interior, but getting to go on the rooftop was a unique experience.

Unfortunately, while my legs and knees were holding up fine, all of the looking up for photos did a number on my back, and I called it a day earlier than intended, although I did stop at Ciaco for some more gelato on the way (purely medicinal). I went out for dinner and decided to get some traditional Milanese fare at Ristorante Nabucco (where I had oso bucco with risotto). I had looked at a restaurant closer to the hotel, but couldn’t get anyone to pick up the phone to take a reservation, whereas Nabucco took my reservation for one online (which would turn out not to be a given as I went further along my trip).



Early stages of entry for the Last Supper; everyone trying to get their photo

You had plenty of time to observe the painting and get all the photos you wanted

I wanted to wait to reserve my rooftop tour until I saw the weather, but when I was doing a dummy booking to get familiar with the process 10 days before, Saturday was already sold out, so I booked Friday.

Great to be able to see the details without having to climb so many stairs

I felt a little uneasy walking on the actual roof.

Huge interior space

Close up of the choir

Some fine stained glass

St. Bartholomew Flayed

Following your TR, thanks. Interesting itinerary

Hm, really dark interior. And I guess the camera shows it automatically a bit brighter than it really is. But the rooftop - wow! Getting so close to these Gothic structures is well worth the effort!

Love the first picture with all the smartphone screens in front of the cenacolo. LOL

Keep it coming, I am following along!

I am on a train to north Italy now, and catching up on my reading.
Sounds like a nice trip.

Enjoying your trip report as we were in Milan in October 2025 and were so happy with the Gran Duca di York Hotel. I would recommend it in a heartbeat as clean and comfortable, great location, friendly and helpful staff, nice happy hour with complimentary glass of proseco as well as nice included breakfast buffet in a charming room. Practically adjacent to the hotel is the Pinoteca Ambrosiana which was outstanding. Loved the Duomo and we were lucky to visit the La Scala Museum when we came back to Milan for two nights at the end of our trip. At the La Scala Museum, there is a box with views into the Opera House and we were able to watch a rehearsal with Manfred Honeck conducting and the acoustics were great.

Wonderful, twk! DH and I made Milan a day trip from Verona. We lucked into snagging a cancellation for Last Supper. Happily jealous that you saw a la Scala performance... nothing we could afford same day but did visit the museum.

More soon please... and more gelato. 😇

Thanks for all the comments

Saturday, May 9. Having seen La Scala during the performance on arrival day, I opted not to go take the museum tour there, despite having reserved a 10:00 a.m. ticket, and instead opted to go to the Pinacoteca di Brera, which featured mostly Italian renaissance paintings (a Caravaggio being the prize of the collection). I opted for this, in part, because Brera opened at 8:30, before the crowds would descend on the tourist sites. Not a must see site, but a nice museum in a very gentrified neighborhood. I think my favorite work was Supper at Emmaus by Caravaggio.

From Brera, it was a short walk to Sforza Castle. I opted to simply check out the exterior and the park, rather than stand in line for another museum, which had Michelangelo’s last sculpture, his unfinished Pieta. Using the audio guide while taking photos at the Brera museum had, once again, irritated my upper back (I guess that’s a collection of muscles that I don’t use often enough), so I was ready to cut my morning activities short, head back towards the hotel, get some lunch, and a little rest for my final museum stop in Milan, the Pinacoteca Ambrosiana, maybe 50 steps from my hotel, where I had a 2 pm timed entry. This was a much better museum experience, with a more interesting collection (including Leonardo’s Codex Atlanticus), and also had an audio guide app which I downloaded to my phone and listened to on my earbuds. Much easier than holding something the size of a small flip phone to your ear. I had a rather mixed experience with audio guides on this trip. I should have carried my earbuds with me everywhere, but didn’t do that because they don’t fit in my jeans pocket all that comfortably. As a result, there were a few museums where I was not prepared to take advantage of a downloaded audio guide.

After exiting the Ambrosiana, I took one last walk around the duomo neighborhood, and took advantage of the sunny weather to get some exterior shots of the duomo that I had missed on previous trips. After I got back to the hotel, I downloaded my photos to my iPad, and was a little irritated to discover that I had managed to miss out on geolocation data for the last two days of photos, probably due to switching Bluetooth off and on for the iPhone so my earbuds would connect with the iPad instead, from time to time. I had not noticed this, in part, because I had neglected to study up on the features of my still relatively new Sony RX100VII camera, which is much more complicated to operate than my old Nikon. On Thursday, I had a mild panic when I thought the screen display was broken, only to realize that I simply cannot see the display (at least not in bright sunlight) when wearing my polarized prescription lenses, and in the process managed to unwittingly change my display settings. So, now, when going out sightseeing, I have to think about which glasses I am going to want to wear and/or carry.

After diagnosing my camera issues, and taking a little nap, it was time for dinner. I had some trouble getting reservations at a place or two so went down my list and found one that had online reservations, Osteria al 29. This place was run by Neapolitans (they had the obligatory Diego Maradonna image on display). I couldn’t decide between pizza and pasta, so the chef said, why not both? I took his suggestion had some gnocchi and Quattro formaggi pizza. Both were good, but I could only eat half the pizza, having started with the gnocchi.

Then, it was back to the hotel to get things packed for tomorrow’s train trip to Cinque Terre.

A word about Hotel Gran Duca di York. I loved this hotel and the location. I took a double room rather than a single, but it was worth it as a single would have been quite tight. Great bed and unbelievably quiet, given how close it was to the duomo. Great to be able to walk to the duomo and La Scala. Frankly, I could have walked everywhere but the tram stop nearby made using the tram easy (tap and pay instead of buying tickets) and useful a few times. I took a couple of subway trips, too, just for the experience.



The Brera museum was my first stop Saturday morning




A short walk from the Brera brought me to Sforza Castle


The Amrosiana museum, just steps from my hotel, had an interesting collection.



The Codex Atlanticus was a highlight

Another beautiful day for strolling around the Piazza del Duomo

Funny you should mention the acoustics, because for a symphony concert, they set the orchestra up on a platform over the pit and the front part of the stage, barely getting behind the curtain, then setting up a concert shell for acoustic purposes. During the Mendelsohn piece, I thought the shell might have messed up the acoustics as I could really hear the trumpets cutting through, even when they didn't have a featured part. However, during the Dvorack piece, which, unlike the Mendelsohn, also included low brass, I could still hear the trumpets a bit too much, whereas the trombones and tuba (situated in basically the same position, just to stage right) never were never overpowering. I think the trumpets just had what we used to call "first trumpet syndrome" back in my high school band days.

Sunday, May 10. Today was a travel day, and since it was raining when I left Milan, and overcast when I arrived in Monterosso, not a lot to report. I left the hotel for the train station at around 10:30, even though my train was not until 12:10, because I wanted to get something at the station that I could take with me to eat on the train. I was glad that I had watched some YouTube videos about the Central station because that place is huge. Even though I knew the general location of the food court I was looking for (which must have had 20 different food options, ranging from hamburgers all the way to steak Florentine), I would never have found it if I didn’t know it was there. The train ride was a direct 2:55 minute trip to Monterosso with no changes. It was raining in Milan, and had been raining in Monterosso, but it stopped just before my arrival. The walk to apartment with my luggage could have been a real slog, but there were no steps from my station to the apartment. Other than make the move from Milan to Monterosso, take a little look around Monterosso, and grab some dinner, that was about all I did on this day.

My apartment at Via Roma 88 was rented through VRBO. It is a one bedroom apartment, and I would say it was a little on the spacious side for Cinque Terre apartments. My host, an elderly lady who lived in the same building, didn’t really speak any English, but we communicated just enough to get the job done. She contacted me a few days before arrival and was there to meet me at the apartment. A nice comfortable double bed provided a very good night’s sleep, once everyone else in the building had retired for the night, and this place is far enough up the Main Street that things get quiet at an appropriate hour.


A little rain on Sunday morning, and Piazza del Duomo was very quiet at 9 am

My apartment building, up towards the top of Via Roma in the old town of Monterosso. My apartment is the one just below the satellite dish.

A less than perfect weather day still didn't chase away the crowds in Monteorosso. Still some cruise ship groups walking the streets when I arrived

Monterosso might be the least picturesque of the five towns, but it's attractive enough, and has a lot to offer

Fellow tourists making the trek from the tunnel connecting the train station and new town with the old. One great thing about Monterosso was that there were no stairs between the station and my apartment

The castle on the point separating the old town from the new town

A view from the start of the trail to Vernazza

Good to know that you found the Ambrosiana more interesting than the Brera. Another Nikon camera guy here - and I refuse to buy another one. Just had my D7000 with AF-S Nikkor 16-85 inspected and minor repairs done ;-)

The Milan hotel is bookmarked. A bit on the expensive side, I thought, but maybe you need to pay that for good quality in Milan.

Monterosso looks nice, even in / after the rain.

Monday, May 11. Before the trip, I purchased the 3 day Cinque Terre pass for the trains and the trails. I always like maximum flexibility, so was willing to pay the €49, even though I didn’t end up using it on the first day. Had the weather been decent, I would have ventured out beyond Monterosso Sunday evening, but it wasn’t, so I didn’t. However, the forecast for Monday was for rain until early afternoon, then a possible break in the clouds late in the afternoon.

When I booked my pass, I had the option to also select a time to do Via Dell’Amore, the improved walkway between Riomaggiore and Manarola. I would sort of compare it to the pedestrian version of the Pacific Coast Highway at Big Sur. Ideally, I would have waited and reserved a time later, but, with Sunday not being feasible, and a cruise ship due in port at La Spezia on Tuesday, Monday seemed to be the choice, and I went ahead and selected 11:30 on Monday out of fear that the slots that looked better once the weather forecast was known would not be available when I made my selection, much like what happened with the duomo in Milan.

As it turned out, the weather in the morning was not good, but, it at least stopped raining, for the most part, once I got to Riomaggiore after 10:00. I took a little look around town, and because the day trippers were not out in force, I was able to get the classic shot of town from the harbor without having to fight a crowd (only had to wait for one narcissist with his iPhone on a tripod taking photos of himself and his girlfriend). After that, I killed some time waiting for my timed entry, then did the 20 minute leisurely stroll to Manarola. Rain was picking up again, when I finished, so I didn’t go into Manarola proper, holding out for better weather tomorrow, and resolved to go back to Monterosso, have lunch, then take a nap to wait out the weather and see if it would clear enough to make it worthwhile to do the trail between Monterosso and Vernazza, a physically demanding trail (at least for a very sedentary 59 year old lawyer) which I had essentially prepared months getting myself in shape to tackle this.

I set an alarm for 3:45, but the sun woke me up at 3:15. I hurriedly got dressed and headed out to embark on the trail. Or should I say, trial. Buon Dio, what an ordeal! Now, it would have been slightly easier on a perfectly dry day, but this trail, in these conditions, was all I would want to tackle in the way of hikes. The climb up (whichever way you go, starting in Monterosso or Vernazza) requires a lot of exertion, but I managed that simply taking a few breathers. Some younger folks overtook me (OK, maybe some of them weren’t younger than me) but after a while, it was mostly me and a French couple moving at more or less the same pace. I think that’s because, shortly after hitting the trail, the weather at Monterosso took a turn for the worse. In fact, when I started up the trail, I could see that it was still raining up in the hills above Vernazza, but, I placed my faith in the weather forecast and radar I was seeing, and plowed on.

Once I was near the top elevation on the trail (I think), about a third of the way along, people passing me were talking about how it was about to start raining. I wanted to travel light, so didn’t pack any rain gear in my little day pack, so I would have been screwed if it had started raining. I also could have used some first aid supplies because, as I am prone to do, I somehow cut myself on my right forearm. This happens to me regularly, and I didn’t even notice until someone pointed it out to me and asked me if I was OK. Lacking so much as a napkin, I didn’t really have any way to clean it up, and, as a result, people on the trail constantly asked me if I was OK. It’s nice that folks were concerned, but it was also embarrassing to have to explain that I was fine and didn’t even feel the injury.

Once I finally got on the downhill portion closer to Vernazza, the physical exertion wasn’t nearly as big, but, having already cut myself, I didn’t want to further alarm my fellow hikers and was very careful (meaning very slow) working my way down the primitive steps on this old donkey path. Going up was just a test of your strength; going down was a test of your nerves, especially in these conditions. I used whatever was available to brace myself: the occasional railing, but, more often, trees, rocks, dry masonary fences (which were jagged and quite possible of inflicting further cuts), chain link fencing and fencing made out of rebar. I was beginning to wonder if the effort was going to be to worth it, but, just when I was at my lowest point, Vernazza suddenly came into view. I took some photos (didn’t take many on the trail as I didn’t want one hand to be occupied with caring for my camera), and, when the next viewpoint came up, I was elated to see the sun peak out of the clouds and got some glorious picture of Vernazza in the sunshine.

Satisfied that I had achieved one of my major goals on the trip, I decided that I would save exploration of Vernazza for the sunny weather promised for Tuesday, cruise ship guided tours flooding the streets or not, and made my way back to Monterosso for dinner. When I got off the train at Monterosso, I could see that it was raining back in Vernazza, and could not believe how lucky I’d been, both in getting my desired pictures and not ending up finding out how good the medical coverage really was for my travel insurance.