Everybody should have a fantasy destination. Some place that they dream about visiting a little too much. Gives you a goal, you know?

For Rebecca, Italy is that place. She’s wanted to visit it since she had a toddlery afro. Maybe even before. So imagine her delight when we had time enough at the end of our travels to spend a whole month there.

Our trip took us to Venice, to Milan, to Florence, to Syracuse, to Sorrento, and finally to Rome, where we stayed for a whopping ten days.

Let me walk you through it:


It started with a train ride from Munich.

descrip The face of fulfillment.

The scenery outside the window outdid some of the prettiest destinations we visited:


Not that I saw any of it: descrip

After 5 hours of whizzing through the Alps we got to Venice.

It enchanted Rebecca immediately. She, like me, is a sucker for municipal ferries: descrip

Though, wow, those rides were pricey. Much like everything in Venice (more on that later).

We stayed out on Lido, an outlying island from the city. I’m happy we did, because we got to experience a strange Lent-related (?) festival, that, as far as I can tell, was only on the island:

descrip descrip descrip

I couldn’t really connect the dots between Snow White and Lent, but this guy came over to explain it to us:

descrip He was super helpful:

descrip Reba had a great time! descrip Don’t worry, we did other things beside getting pummeled with confetti.  We saw a lot of the tourist stuff, like the Rialto Bridge:

descrip and the Piazza San Marco:descrip descrip descripBut mostly we just took strolls around scenic, scenic Venice: descrip descrip descrip Now, confession time: I’m not a big Venice fan.

I understand why people love it. I really do. It’s gorgeous. Reba loves it, even.

If I’m gonna be in Italy, though, I’m there for the food. And Venice just ain’t the best place for it. 

More often than not the restaurants you’ll stumble upon will be the kind of joint where you pay 80 Euros for warmed-over Boyardee. So, so sad.

The next town had a much better scene for that.


The experience of walking through Milan in my raggedy travel clothes was…humbling. Fashionistas abounded around there. But, so did excellent food. Somehow, someway, we had so many vegan and gluten-free food options for Reba.

Our favorite was Bebop. I stole this image from Tripadvisor because I didn’t take any pictures of our meals.

descrip Trust when I say it was outstanding.

We only spent a day here, but it was long enough to eat some good food and see our good friend, The Last Supper.

descripThis pic isn’t mine either.

Overall I loved Milan. Aside from the food and the one painting, the nightlife gave the impression that Italians know how to have a good time.

It was a quick trip there, and then off to one of my all-time favorites from days’ past:


I saw Florence back in 2007 and I loved it back then. I couldn’t wait to come back. What a gorgeous place. Home to one of my favorite buildings ever, the Duomo di Firenze: descripdescripWay too pretty.

A good friend once told me that the multicolored marble looks very lick-able in person. He’s right.

Florence is also home to another old buddy: descrip Here’s a fun factoid about his penis.

A lot of people make fun of David’s unit for being so small. Lots of smirking remarks about how he’s supposed to be the apex of masculinity, but with one serious defect.

However, recent research into Michealangelo’s journals has shown that the artist intentionally incorporated some shrinkage.

Remember, David is supposed to facing down Goliath, so we’re looking at a man full of tension and fear.

And what do you suppose happens when a man gets scared? That’s right.

That’s not to say that the piece is completely flawless. There’s one minor mistake:


See that divot near his right shoulder? You wouldn’t find that on an ordinary person’s body. Michelangelo apparently had some defective marble on his hands, and this forced him to create less-than-perfect back anatomy.

We had a delightful time in the city. It was two-a-day pizzas, mid-afternoon gelatos, and campari spritzes every evening for a week.descrip Look at that eggplant, man!

I sold Rebecca on the place, that’s for sure.

Although, I didn’t think it was possible, but I enjoyed our next destination even more.


It took a looooooong time to get there, though. We had to travel all the way down the boot, and then some, to the island of Sicily. descrip Long day

You might wonder how the train makes that little jump across the water. Here’s how it’s done. descrip Shunting

That’s a train shunted into the cabin of a ferry. Genius! It looked like this on the top floor:

descrip The top floor

The ferry dropped us off late in the evening in Syracuse. The town is a great place for history buffs — the Greeks settled there before the Italians did, and they left their mark. Most notably here: descripThe Duomo di Siracusa

That Christian exterior is all pretty recent. But it was built as the new face of the Temple of Athena, which the Greeks set up in the 5th century BC. Here’s what that foundational structure looks like:

descripAthena in church

Love this building.

Syracuse also happens to house what used to be one of the largest Greek amphitheaters of the ancient world:

descripReba for scale

Not too shabby. And Syracuse also happened to have the world’s best sandwich shop: Caseificio Borderi. Way too much to handle.


You walk in the door and the owner immediately forces globs of ricotta into your hands. Then you ask for a sandwich. No menu, just “I want something spicy” or “what goes well with your olives?”, and they slap something together.

descrip descripThey work hard at Borderi. We went there three times in two days, including 3 to go subs (each) for out train wide to…


We seriously scored here. By complete accident, we booked a room at this family home situated on a lemon / orange orchard.

descripThey even had homemade limoncello.

Plus this guy ran the joint:


Not literally. But the manager was a pony-tailed Neapolitan who worked for a family friend in New Jersey for a few years. Close enough for me.

Sorrento itself was dazzling, too.descrip descripAnd it was an awesome sightseeing base, for stuff like the ruins of Pompeii… descrip Look at that Vesuvius! descrip And those gorgeous teeth! …and the isle of Capri, reachable only by ferry: descrip descrip Capri is unspeakably beautiful.

We took a ski-lift all the way to the top: descrip WEEEEE

And this view awaited us:

descripCould do a lot worse.

Sorrento obviously didn’t disappoint.

We didn’t even have time to think about how sad it was that our next city would be our last. On the whole. 8-month-long. Trip.


Woah. There it was. The ancient West’s biggest deal. And wouldn’t you know it — I got horrifically sick.

I came down with some kind of fever, coupled with stomach stuff. Reba too. I spent 3 entire days in bed! That means I missed a few photo opportunities.

Reba went out and saw the Coloseum without me. And some other ruin-y stuff. But when I got well again we got ambitious.

Saw a little bit of this: descripdescrip BOOTS!

And a little bit of this: descrip And some St Peter’s Square:descripAnd some Pieta: descripAnd the Vatican’s map room:descrip descripAnd the Pope (briefly, from far away): descrip FRANCIS!

And the REAL Pope:


And several dozen of these: descrip

Now, as much as we liked those pizzas, they didn’t stack up to the Two Big Meals we had in Rome.

The first of which was at Stazione di Posta, a hip modern place descrip The Stazione

in a weird, weird location: descrip Zuh!

descrip Nerg?

It was waaaay out in the middle of this barren lot, far from the city center, and next door to a children’s library.

The food more than made up for the confusing walk out, and then the expensive Uber home.

The second of the Two Big Meals happened on our very last night, at La Pergola, which is on the top floor of the Waldorf.

If that sounds fancy to you, you have good instincts. It was crazy fancy. Too fancy to even photograph the food. But here’s us enjoying it: descrip And here’s the view of the Vatican from the balcony: descrip

I’ll only say about this meal: single best one of my life. And the wine was just as exciting as every dish was.

It was a fitting send-off to the whole travel experience. Reba and I have an awful lot to reminisce about.