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Mark far above the lighthouse on the southwestern tip of the island

After four nearly perfect days in Capri we took a very quick taxi ride up to Anacapri, the somewhat higher, quieter, more relaxed community a bit west of the main town. It was supposed to be four more days of hiking, beach time, and restaurants. We’ve stayed in both Capri and Anacapri on various visits and like them both in different ways. For this stop we stayed at the Capri Palace Hotel, where we’ve stayed before, because it has both a nice pool (with great pool service in the past) and a private beach club associated with a Michelin-starred restaurant for glorious lunches. We were quite looking forward to the stay.

Alas, we had not factored in four days of rain. Not that tropical stuff you get in Southeast Asia where the weather is fine most of the day, then a big rainstorm rolls through and then it’s fine again. This was just rain and threatening clouds nearly the entire day. For four consecutive days. We could do some walks, but a several hour hike around the western end of the island was out of the question – no way you could escape the rain for that long.

The view from our room. Normally you would see clear skies and fabulous blue water. Not these four days.

So little of the beauty that we love about Capri and essentially none of the pool or beach time we were so eager for. And to be honest, we were kind of bored much of the time; there’s only so much time you can spend researching restaurants for lunch and dinner. Had we been in most any Italian city there are always museums and churches to go to. Even cafés to duck into. Not here though. Shorter walks during breaks in the weather were possible but that was about it.

I did manage one adventure that was worthwhile. On our last afternoon it looked as though there was going to be a couple hours without rain so from Anacapri I walked down to Capri (it’s a lot of steps…), hung out there for a while, and climbed back up again. And since I had already hiked from Capri to the northeastern tip of the island (and back) and from Anacapri to the southwestern tip of the island (and back), that meant that during the eight days we were there I hiked from one tip to the other – and back again. Not bad for an old man.

Stairs down, down, down from Anacapri to Capri

And that was enough. Even under clouds the island has its charms, though I can only imagine what the experience was like for the many MANY day trippers who’d heard about the beauty of Capri and seen the pictures and all that, and then come for a day in the rain. Probably not as much in love with the island as I have been for 50 years.

Next stop, Naples!

A horde of day trippers on a rain-soaked tour of Anacapri

An amazing variation on a Caprese salad at Da Emilia, a great new find for us that we went to a couple of times. And my excellent steak tartare in the background.

The empty, rain-soaked main square of Anacapri

There were occasional glimpses of blue sky, but they weren’t common and didn’t last long. This tree, quite near our hotel, has featured in many of our photos from Anacapri over the years.

Dinner at Il Solitario, another new find for us that was worth going back to

Out on the southwestern corner of the island is an odd park. It’s called the Philosopher’s Park, endowed by an old Swedish academic who loved Capri and left this land to be studded with glazed plaques and quotes from great philosophers over the last few millennia. It was surprisingly serene and I would have stayed for a good while here except it was obvious a big rainstorm was brewing.

From the edge of the Philosopher’s Park you get this view up island over the famous Fraglioni rocks

The town cemetery, another serene spot

Our beautiful and almost completely unused pool

On a walk

The view from Anacapri across the island and over to the mainland, Sorrento, and the Amalfi Coast

There are a lot of mediocre restaurant serving the tourist hordes in Capri, but Da Tonino, a 20-minute walk from town, is perfection

From Palermo we took an overnight ferry to Naples, where we would catch a morning ferry to the island of Capri, one of our favorite places in the world. But first let’s talk about that overnight ferry.

We did the same ferry in reverse 13 years ago, setting out from Naples for our first ever visit to Sicily. We didn’t really know what to expect, but it was a really fun experience. Soon after we settled into our modest private cabin we went looking for dinner. First we checked out the “cafeteria,” a huge space teeming with tons of people filling plates with sloppy looking, seemingly low budget food selections. Then we looked for the “restaurant” and found a shockingly elegant space with white tablecloths, white-jacketed waiters, a lovely menu, and hardly another soul dining there. There we had one of our most memorable meals ever.

As we prepared for this repeat journey I was wondering if that amazing, improbable dining experience was still an option. I asked ChatGPT about it, and they confirmed that yes, this route still has both a crowded cafeteria and an “elegant” sit-down à la carte restaurant. Yay, another fun travel experience to look forward to!

Now, it turns out that ChatGPT is sometimes just wrong. And while there was still technically a table-service restaurant, it had been seriously downgraded. No tablecloths. Surly waiters. Not a great menu at all. And just to really rub it in, they had put the boat’s children’s play area immediately across from this restaurant so diners could enjoy the screaming and squealing of the ship’s loudest and most boisterous passengers. Our dinner was a shadow of the faded glamour we’d hope to recapture.

But we survived and made it to this beautiful island for the first time in nine years. We are nearing the end of the summer season, and we got four days of the perfect weather we hoped for. Sunny. In the 70s. A little breezy. And the sea water warm and bright blue.

What do we do in Capri? Most days we head to one of the beach clubs. The island has no actual sandy “beaches,” but these elegant clubs have grown around rocky outcrops where you can jump into the sea and climb out by a ladder. Or you can walk over uncomfortable pebbles until you are relieved to fall into the soothing water. And then you have an elegant Italian lunch overlooking the stunning land and seascape.

La Fontelina is a popular beach club that we’ve been coming to for years. The views from here are among the absolute best. But I was a bit annoyed at how outrageous the prices were this time!

Lunch at La Fontelina

Lunch at our hotel’s own beach club near Marina Piccola. They are newer and don’t charge nearly the prices that La Fontelina does, yet the service and food were way better.

Enjoying the warm blue October water

What you don’t do is walk through the cute town during the day because it is completely overrun by hordes of day trippers. I don’t know how many thousands of people are dumped off here by the ferries and cruise ships, but they are really a menace. They crowd the central streets, form huge lines at the gelato shops, and make it a chore to get around. From about 11 am to 5 pm they are jammed into the central square, sporting their wrist bands, ID stickers, and lanyards around the neck. Big clusters wear headphones as they follow their flag-bearing guides.

And then as evening comes on they all go away and peace descends again.

From here we’ll travel up the island to spend another four days in the charming town of Anacapri. But as we look at the weather forecast, we fear the summer season is abruptly coming to an end!

The iconic Faraglioni attract yachts of all types and a gazillion photos

The narrow lanes that snake all over the island

The hordes of day trippers that jam the center of town during the day; note the skinny little trucks that carry luggage, food, and supplies through all the narrow roads all over the island

A peaceful aperitif in town after the day tripping hordes have cleared out

Lunch at Da Tonino

The comfort of Al Grottino, a reliable restaurant we’ve returned to numerous times over the years

Everything that we love about Palermo. Narrow streets, beautiful colors, crumbling architecture, graffiti. OK, everything we love except the food, but that’ll come later.

Let’s start with the ugly and then go to the bad, so we can end with the good.

As there is no direct flight from New York to Palermo, we flew on Swiss Air through Zurich. We had a pretty tight layover and then our flight was maybe 30 minutes late so we just barely made our connecting flight. Sadly, though, our luggage didn’t, even though the plane sat at the gate for something close to 30 minutes before pushing back. As we were walking towards baggage claim we each got a text from Swiss Air that our bags would be on the next flight that evening and, if we would just fill out this online form, they would deliver them to our hotel. Great, we don’t even have to wait for the bags. Easy peasy, right?

Yeah, not so much. Basically we didn’t hear from them for a couple days. I’ll spare all the details but basically because Mt. Etna was stirring things up on the other side of Sicily, all the Sicilian flights were routed through Palermo and the airport was unbelievably chaotic. When we started to hear from others just how bad it was I realized the only way we were going to get those bags was to go to the airport ourselves. And I needed my bag more than I normally would; somehow I’d lost my eyeglasses on the flight to Zurich and I needed the spare pair that I’d packed.

Hordes of people desperately trying to get to security to board their flights. It was pure chaos that I somehow had to get through.

Ultimately it took me two trips to the airport to find the bags, the first being just this dystopian experience of hundreds of people crushed together in some scrum trying to get to their flights. And because it was an International airport where you go through customs before leaving the airport, the bags were behind security. After struggling with forms and police and Italian bureaucracy, I had no choice but to give up; there was no way I was getting through that mess. I decided to try the again the next morning, thinking maybe if I got there early enough it wouldn’t be so bad. Boy, was that the right call. Getting there before 8:00 AM, I breezed through security and found the bags in just a couple minutes. There were hundreds of lost bags just lined up all over the arrival hall; it’s hard to imagine that Swiss Air ever would have gotten them to us on their own.

Our hotel was beautiful, but too far from the city. And a big construction project right next to the hotel didn’t help.

OK, it was a hellish experience, and being without clothes and toiletries isn’t fun, but eventually we had everything. The next problem – The Bad – was that the hotel we’d booked was a lot further out of town than we’d thought. As in, over an hour’s walk to the historic center, and much of that through an unattractive port area. That meant every time wanted to go in for lunch or dinner or to tour around we’d spend 20 minutes on each end in the hotel shuttle or an Uber. Now, the hotel was really nice and had beautiful grounds and good food, but we’d come to Palermo, well, to see Palermo. Oh, and if you did want to just hang out at the pool with a great view of the sea – which I certainly wanted in the morning – there was a major harbor renovation project immediately adjacent to the hotel. Sometimes it was bearable, but sometimes it wasn’t.

The good news, though, is that once we got all that sorted – got the luggage, come to terms with time wasted in cars and shuttles – Palermo was great. Just wandering around the historic center with its narrow streets and gritty charm packed full of character. Graffiti everywhere, clothes hanging from second and third story balconies, scooters zooming back and forth. We visited the cathedral, a museum, and a couple interesting churches, found great places to eat, and just leaned into the start of three weeks in Southern Italy.

Mark atop the Cathedral

It’s worth emphasizing that “southern” adjective. We have long preferred the south to the north: better food and more vibrant culture. But it’s been several years since we’ve been down here, in large part because summer weather in Italy is so brutal these days. So finally here we are in late September and October and so far at least the weather has been cooperating brilliantly. Next stop, an overnight boat to Naples and a quick connection over to Capri. That should be good.

Just a normal streetscape in Palermo

Scooters and narrow streets

Speaking of colorful, narrow streets

The streets are even more colorful than I am

Eating and drinking happens out in the streets too. We stopped here for a drink before dinner and ordered a double, because Europeans pour their drinks so small. Not here, though – this was huge. We went back.

More outdoor dining

We spent time in the Cathedral, a church or two, and a couple smaller chapels

Sicily is famous for the stucco sculptures in the churches and chapels

Definitely not into minimalism

Since Sicily was the crossroads of the Mediterranean that everyone conquered at one time or another, there is a lot of variation in the art and architecture. Here the Church of St. Mary is covered in gorgeous 12th century Byzantine mosaics.

Mark was into this Jesus with … contemporary jewelry

The Palazzo Abatellis is Palermo’s premier art museum, and this Annunciata is considered the star. It was so modern looking I thought it was placed just as a counterpoint to the older stuff, but indeed it’s a 15th century Renaissance painting.

The other star of the show is a 15th century fresco, Triumph of Death. In this closeup a lot of people have been mowed down by arrows.

One more piece from the museum

And there were other joys in Palermo. I spent a few hours in the Botanical Gardens that included this massive ficus tree, named Italy’s Tree of the Year in 2023. Pretty impressive.

Not all of Palermo was this green but there were a few spots

A harbor with a lot of sailboats

The view from breakfast. If you ignored the construction noise and the distance from the city center it was a great place.

And finally, a guy selling drinks out of a mobile orange. You gotta love Palermo, right?