With travel, sometimes sour grapes lead to the sweetest delights

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I’m a planner. I can’t help it. Even on unstructured days off, I create a mental schedule of things I want to get done. So naturally, planning our family vacation to Italy became my domain. I embraced the joys of reading Airbnb reviews and researching the coolest things to do — at least in my opinion (which is what mattered since I was doing the planning).

I discovered a great little apartment in Amalfi, where I could gaze out at the sun rising over the town every morning right from my bed. While I looked forward to spending six nights in Amalfi, I thought, what would be the harm in doing a quick overnight? So I scoped out the resplendent island of Capri. I read that the town of Anacapri provided an “authentic” experience — I wasn’t sure what that meant, but it sounded really nice! It was enough to convince me to book a 2 bedroom apartment with a panoramic terrace at a fantastic price point!

The day before our overnight, I saw there was a ferry to Capri at 9:50 am. We’d have the day and evening to explore the town. Before taking the ferry back for our final evening in Amalfi, I also scheduled a 3-hour boat tour for the morning.

  • Ferry schedule: Check. ✅

  • Airbnb with a ride up to the town: Check. ✅

  • Boat tour: Check. ✅

  • Planned unstructured free time: Check. ✅
    What could possibly go wrong?

We woke the next morning and loaded our backpacks with our overnight supplies eager to get to the ferry station to purchase our tickets…only to find a sign that read NO Ferries. We wouldn’t be so easily deterred. We walked to the information kiosk to see what options were available to get us to Capri.

“We need to get the ferry to Capri,” we said.

“No ferries, it’s too rough,” said the bored and irritated 20-something sitting at the desk.

“But how do we get to Capri?”

“No ferries,” she replied. “You have to take the bus.”

“But buses don’t go to Capri,” I pointed out. “We need to take a ferry.”

“No ferries,” she replied.

“I understand that there are no ferries from this location, but can we get a ferry from Positano?”

“You have to take a bus,” she said.

“A bus to Positano? Can we get the ferry from there?” I inquired.

“No ferries,” she repeated.

Eventually, we realized that the attendant meant to say that we needed to take a bus to Sorrento, 2 hours away.

“And from Sorrento, we can take a ferry to Capri?” we questioned the attendant before leaving.

“Of course,” she said (as if this was THE most obvious thing in the entire world).

At this point, my husband Peter (bless his heart) said the most sensible thing we’d hear that day, “Okay, well, we aren’t going.” WHAT? But this was the PLAN!

We got in a (very long) line for the bus to Sorrento, Peter fuming. Me fuming. Our girls were… well, they were on their phones. After a 20 minute wait, we were next to board the bus, but it was packed to the gills and closed its doors right in front of us. The next bus was 45 minutes away.

“That’s it, we’re not going,” said my sensible husband. Seriously, he clearly did not understand THE PLAN! I sent him off to get sandwiches while we held our place in line, smug that we’d get excellent seats for our two-hour bus ride.

A quick side note about bus rides on the Amalfi Coast: there is certain death at any interval. The views were breathtaking… or maybe we were just holding our breath as the bus flew around impossible corners scattering Vespas as they forged their way along the cliffs, confident in the Alpha state of size and mass.

We eventually arrived in Sorrento, albeit a bit stunned and nauseously green. We discovered that the ferry station was all the way down at the bottom of a cliffside town. As we began our descent, I couldn’t help but think If there’s no ferry, I will never hear the end of this. Luckily, we made it safely down and began waiting for our ferry to Capri.

The ferry ride was the sickest version of a roller coaster that you could possibly imagine — the reason why most of the ferries weren’t running was that the seas were too rough. Crew members began passing out plastic garbage bags to passengers in anticipation that the waters would be too much for some to bear. We held on for dear life as we began chugging through the rough waves. Suddenly, the crew started shouting at us all to move towards the back of the ferry — the safest and most stable place for us all to be. Could this get any worse?

This way to paradise! ©Body Synergy Fitcation

30 minutes later, we arrived on land and jumped into a taxi that sped up a very steep and curvy road to the top of the island, the “authentic” town of Anacapri. We then discovered what “authentic” meant: winding medieval streets, twisting and turning, designed to confuse pirates and tourists. We finally arrived at our Airbnb. Remember that panoramic terrace? Well, it was — the ocean was breathtaking. But the rest of the apartment was dark and shabby. Not that it mattered, I figured, because if we left, we’d never find our way back. I flopped down onto the bed face first, the springs shrieking in complaint. I had ruined our vacation, this was a horrible mistake! My wallowing was interrupted, by my teenage daughter, Jenny, and her best friend proclaiming that they were hungry. Seriously!?

We left our bags and foraged out, taking photos of the streets as we passed, my daughter confident in her ability to find our apartment again. We found an area with a few tired looking shops and restaurants, and after a heated discussion about how to find the best food, my daughter plopped herself down at the first place she saw and refused to move, her bestie sitting down next to her in solidarity. I noted that there was a bar and followed suit, reluctantly followed by my husband. There was a Negroni, or two. Then bruschetta and pizza — all of which tasted remarkably good. Somewhat mollified, I began to look around the town and noticed two little girls in folk costumes walk by… and then two more. All of a sudden, there was a group of 15 little girls with their families taking photos, some of whom were also dressed in costume.

I asked the owner of the little cafe about the costumes.

“You mean you don’t know?” she asked, clearly shocked.

“Um, no,” I said, embarrassed.

“Today is the first day of the Settembrata Anacaprese,” she said. “It is our festival of the grapes! It will be a huge party!”

“Wow, great. Where is it?” I asked.

“Just go outside,” she laughed.

The doors of the sleepy little town burst open, and the streets were flooded with costumed people laughing and dancing. Someone spun me around and shoved a cup of wine into my hand. I drank it, and the empty cup was replaced with a full one, again and again. There was a marching band, an unlikely mix of grizzled seniors and clean-faced high schoolers playing authentic Italian folk songs. And the Bee Gees. And Michael Jackson. And James Brown. My normally reticent husband boogied down with the locals. We applauded Mr. and Ms. Anacapri, dressed as town royalty. Teenagers outfitted in peasant attire danced on grapes in a cask, and the juices flowed. I assumed that was NOT what we had been drinking.

We wandered through the streets, swept up by the revelry, drunk on the experience (and some damn good Anacapri Red). We ate grapes and gelato. And later, much later, stumbled into a restaurant full of locals for a stunningly good dinner. Jenny was as good as her word, and we did find our Airbnb that night. The shabbiness seemed charming, the beds comfortable. And we slept, saturated with the experience of the worst-day-turned-best-day of our vacation. An utter, unexpected delight.