Almost exactly 2,000 years ago, Rome’s second emperor completed the construction of his vacation villa. According to ancient sources, Tiberius was already growing weary of the backbiting and politicking required to fill in Augustus’ footsteps. His villa sat atop a 1,000-foot-tall mountain on the island of Capri where would-be assassins and annoying courtiers would have a much harder time getting to him. In time, the vacation home dropped the descriptor; it just became a “home”. Drawn in by the peace and beauty of Capri, no doubt, Tiberius chose to spend his last few years there.
2,000 years later, Elizabeth, Pam, and I found ourselves in a boat bound for the very same island. The method of transportation has changed rather significantly over the last two millennia, but the Sorrento/Capri/Amalfi Coast area of Italy continues to be one of the world’s great recreation and leisure spots. Over the course of a lovely day, the three of us found out why.
But before the peace and relaxation, there was just a smidge of chaos. It mostly stemmed from an overly ambitious early meeting time with our boat tour operator and Elizabeth’s insistence on wringing every moment she could from our luxurious Sorrento hotel room. Fortunately, you can usually end up late to a tour in which you’re the only guests and they won’t leave without you. Elizabeth had time to drink her plain latte while enjoying the view out the window of the Excelsior Vittoria.

We met with our guide right in the hotel lobby, which kind of makes sense when you realize the hotel is right above the little Sorrento harbor. To get down, all you have to do is take the elevator from somewhere on hotel property down into the big yawning cave below (that apparently gets used as a wedding reception hall!) and then you pop out right at the water.

My first indication of how much my life was about to level up should have been the tray of glasses of water on the back of the boat. They were the first thing I noticed when climbing aboard – not necessarily the waters so much as what was sitting on top of each glass.

The captain of the boat was our guide/host’s father. They ran a family business together that peddled in giving simple American tourists like me and Elizabeth and Pam the day of our dreams. Honestly, that’s a cool way to go about it. The two of them were extremely helpful, responsive, and fun to chat with. Before going any further in this blog post, allow me to apologize for forgetting their names and to say that they made this day as special as it was.
With that acknowledgement out of the way, we can pick this narrative up over the open waters of the Bay of Sorrento. As a reminder, here’s what the map looked like spread out around us:

Elizabeth made her desire to see Capri known very early, and our guides readily agreed to take us over there. The boat jumped through light chop along the northern coast of the peninsula for about 10 minutes before bearing southwest across the open water.

Off in the distance, a couple of mountains rose from the water. They were about the only things as far as the eye could see that broke up the endless expanse of deep, Mediterranean blue.

That peak on the left side is Monte Tiberio, the haunt of Rome’s second princeps. If we believe the (hostile) ancient literary sources, this is the spot where Tiberius would throw political enemies off of the 1,000-foot-tall cliff to their death. It sort of feels like there should be more jaggedy rocks at the bottom of the drop-off, but that’s supposedly why he had members of the Roman navy in the water and ready to beat any survivors to death with oars.

That sort of puts modern political struggles into context, doesn’t it?
As you might imagine looking at the picture above, there are several famous caves along the limestone cliffs of Capri. The Italians aren’t any more creative at naming things than an American would be, so our first stop was at Grotto Bianca (White Cave). I guess there are times that you can boat or swim right up inside of the cave, but there was a buoy in place to keep people from getting too close (and I don’t think our bigger speedboat was going to fit into the gap anyway). Our captain explained the local lore, including the so-called Madonna Rock inside of the cave that resembled the Virgin Mary praying, all while surrounded by stalactites and stalagmites. The view from outside of the grotto was pretty good, if not quite the same as it would be inside. You could just make out the Madonna Rock at the top.

We were idling along in the shallow water and it was a reasonably warm – though not outright hot – October afternoon. The boat had one of those big front sections that was upholstered and looked comfortable to sit on. At the enthusiastic assent of our hosts, I clambered up there to lay out and really luxuriate. The water was a brilliant aquamarine that I didn’t know could exist outside of a glacial lake.

Now how could the day get any better?
Oh, this is how.

I’ll talk a little more about the dinner Elizabeth, Pam and I had gotten the night before in my “Food of Sorrento” post (the next one in line in this Europe series!), but it was an extremely fancy meal. But it sort of didn’t count because it was a dinner booked at the (admittedly very post) hotel we were staying at. This right here was my first realization that we were breaking through on this vacation and living a full life of luxury. It was going to be absolutely awesome. Pam, if you’re reading this, I hope I thanked you at the time of that realization. But if not – thank you for those two weeks.

Our luxury cruise continued around the southern coast of Capri. Our boat went around a rugged point that had plenty of offshore rock formations, including arches:

And past the stunning Marina Piccola village:

Could you imagine living in a place such as that? First of all, walking from location to location has to be a hell of a workout, because that slope in town doesn’t look gentle. But more importantly, would you ever tire of the way the sun sparkles over the water, the gentle Mediterranean breeze, or the influx of fresh fruit and oodles of rich tourist money? It doesn’t seem like you would.
It was at about this point that Pam pointed out the minor tragedy of Winston not being here. Evidently he had stayed at home for a few extra days in large part to spend more time with his girlfriend. He and Moira were at a pumpkin patch back in DC and by all accounts having a great day together. Still, with the three of us fully in paradise, it didn’t take long for our commentary to take on the note of gentle mockery. “Winston? Where are you, Winston? There’s no pumpkins on Capri, Winston!”
And somehow things were going to get even more scenic. With all three of us now sitting on the front of the boat, our captain piloted it further westward around the side of a steep, cliffside-pocked mountain. There were staircases and little buildings all over the places, though strangely it was kind of hard to tell if they were Roman ruins, medieval/Renaissance ruins, or maybe something in use today. When everything is designed to fit right into a marginal landscape, eras become less distinctive. Beyond that mountain, there was another brilliant turquoise cape squeezed in east and west by cliffs. We throttled down the speed and made for the very furthest cliff wall itself. Our boat evidently was low-draft enough that it could slide partially under the wall and into the natural wonder known as Grotta Verde.
The grotto really was something. The sun lit up just enough into the grotto for the water to look like it was pouring straight out of a Montana Glacier. Waves gently broke against the rocks with a quiet ebb and flow. The greater noise was generated by other tourists oohing and ahhing – and no doubt, ourselves doing the same.

I know a good “selfie to flex on your friends” opportunity when I see it.

24 hours in Italy and I was already the guy who wore an unbuttoned linen shirt on a boat.
How could you beat something like this? Well, how about jumping into the Mediterranean? The water off of Capri sits at or a little above 70 in early October. Not exactly a tropical paradise, but warm enough and inviting enough that people were jumping off of other boats. Our hosts found a nice sheltered anchorage away from the waves and gave us some time to remove the top layers. Poor me – I’d forgotten my swimsuit back in the USA. So my swim was improvised out of a pair of running shorts that I was planning to sleep in later in the trip (surely we’d find somewhere to do laundry, right?). I went down belowdeck to change in the little bathroom on board – but only the captain, after asking Elizabeth if she had a boyfriend, told her that it was customary to swim naked around here. As a reminder, this was a guy in his 50s with his daughter on board. If it wasn’t so Italian it’d be creepy, but when in Rome, I guess!
One by one we jumped off of the deck and into the brilliant blue waters. Elizabeth took the lead as befitted her position as a former lifeguard, and Pam went last so she wouldn’t have to tread as long. This ended up being less relevant when the boat captain threw us some pool noodles.

The swim was more “memorable” than “enjoyable”, because the air and water temps weren’t that high and who knows what sort of sea monsters live just off of Capri? Fortunately, we got back on board before something down there could nibble off one of my toes. Thank goodness. There was one more tradition for us to learn about when climbing back aboard. Fortunately, it was a little more appealing than “nude swimming at 1:00 pm in full sight of your in-law”. Apparently in Sorrento, when you go swimming, you have to end your swim off with a shot or two of limoncello to warm up. That, we could manage!

Normally you can go all the way around Capri in a single afternoon cruise. However, a steady breeze had apparently raised the chop on the northern side of the island so that the famous Blue Grotto (insanely creative naming) would be unavailable altogether. Nothing to worry about, our hosts said, we could just go somewhere else they knew; nothing fazed them at all. We laid back out on the front of the boat to enjoy the early-afternoon air as the boat sped toward the mainland. However, instead of getting back on the north side of the Sorrento Peninsula, this time we were going to ride alongside the southern side of it toward the famed Amalfi Coast. Who knew what our next destination was? Who cared? Everything else had already been so great.
The destination turned out to be a tiny marina a couple of kilometers past the tip of the peninsula. Our guides found an open buoy in the marina pretty quickly, anchored to it, and called out the tender boat from the shoreline. This was a pretty nifty operation.

There’s a restaurant up there: the Ristorante Conca del Sogno. Evidently it can only be accessed by boat, as there’s no road through the rugged hills behind the marina. I felt ridiculously special and fancy for going to a Hidden Gem spot for lunch on Amalfi Coast. Now, writing this blog post, I see the restaurant has 1,000 Google Reviews. Never let your vibes go up against the modern Internet.
Either way, it was a beautiful sunny afternoon to sit out by the water, order a limoncello spritz, and eat some delicious food. I’ll post the actual food pictures in my upcoming “Food of Sorrento” blog post (hopefully seeing the light of day this August or so), but we’ll let Elizabeth give us the vibe with one picture at least.

Between that the spontaneous dancing from the staff, it was a very Mamma Mia vibe.
The sun had begun to sink lower toward Capri in the distance by the time the marina staff tendered us back to the boat. We had to go all the way around the peninsula to get back to our hotel even though it was no more than 3 or so miles as the crow flies. Before beginning that time-consuming process, though, our guides wanted to give the three of us one more special experience. They felt bad that we’d missed out on Blue Grotto in Capri, but fortunately just a couple hundred meters away was a “less-touristy” grotto. And yeah, compared to the ones from earlier in the day, this one was encouragingly not swarmed with little boats like gnats to a cow.

In fact, if one wants to do so, you can swim right into that cave. It’s Italy, there against doing fun things. This one was kind of fun-sounding, but also kind of terrifying-sounding. Anyone who knows me knows about my mild fear of swimming in oceans, and even with a pool noodle I was a little nervous about entering the belly of the beast. Honestly, I may have opted out of the adventure even after Elizabeth opted in, but then Pam also said she wanted to swim into the cave. And now I was going to be the chump who was the only one to stay on the boat while the other two were exploring. That’s almost as bad as being Winston at a pumpkin patch while everyone else was in Sorrento, but at least he wasn’t here to hear the mockery. Regardless, there was no choice left: I had to put my swimming shorts back on (I bought a swimsuit later that night from a shop in Sorrento. It has lemons on it and is hilariously short) and jump into the water with them.
The inside of the cave was neat. It was good to have pool noodles, because every once in a while a swell would arrive, and the corresponding currents here in the cave were confusing, but tended toward “undertow”. Nobody wanted to be bashed against a rock wall, so we didn’t stay long. Still, it felt like a fear conquered for me.
Where had the afternoon gone? It was 4:30 pm, a full 6 and a half hours after we’d boarded the boat back in town. Unfortunately, there weren’t any more hours to be had. That didn’t mean the three of us were quite done; we sat at the bow of the boat again, sipping waters under blankets thoughtfully brought out by our tour guides, and tried not to get sprayed too badly by the wake getting kicked up. It really was magical. Winston, you made a mistake by going to the pumpkin patch.

Not that there weren’t any mishaps. The funniest one occurred back at the marina as our captain tried to get his boat into one of the narrow docking spots for the evening. Pam was a little slow getting out of the boat and I was hanging nearby to make sure she didn’t get left behind. That’s how both of us were able to hear the most animated invective I think I’ve ever heard in my life from another boat captain. It was in Italian, so I cannot provide a direct translation. But our captain’s daughter told us it boiled down to “Could you please park your boat faster so that everyone else can move, sir?” Except the language was maybe a little less polite. Italy is a land of astonishing contrasts. It’s the place you immediately think of when you imagine drinking a glass of wine and having a late lunch out by the water – leisure defined. It’s also a place where the locals are ready to yell at the drop of a hat, and don’t get me started on the drivers.

I was only peripherally involved in much of the planning for this trip, mostly in Rome and Switzerland. If every day was going to be like this, full of unexpected and incredible surprises, this might end up being the best trip of my life. We only had a single full day in Sorrento. Normally something like a boat tour might have me going “Really?” and trying to find something else with which to spend our day. But no: this one lived up to the hype, and was the best possible way to use that day.
