My Capri Itinerary was pretty much left up to my good Italian friend Vito who lives in Naples and summers in Capri. In very Italian fashion, he instructed me to book my flight and let him know which dates I was coming. I was to stay at his villa and that was pretty much all the information I had.

The only time I was available to go was the last week of August, which is the ideal time to go away for Americans. Vito warned me that Capri would be flooded with tourists from mid-August to September. With that mild warning, I had no idea how extremely populated this small island would be.

I’ve always wanted to visit Capri. As a young kid, my father even had a restaurant named Villa Capri, but funny enough - neither of us had been there until now. From New York, Capri is definitely not easy to get to, but is definitely worth it once you step off that ferry.

After discussing with Vito the fastest, most efficient and most affordable way to get there from New York, was to take a direct, overnight flight to Rome (8.5 hours), followed by a short flight to Naples (1 hour), and a cab from Naples airport to the ferry ports (30 minutes). Now for the ticketing systems for the ferry, it’s not the most advanced. There’s no smartphone tickets you can purchase beforehand, and if you purchase them beforehand online, they need to be printed. Me not knowing this, I arrived to the port that was completely mobbed with people and at least 10 different lines to ticketing booths and no information center. It took us over an hour to wait in line to purchase tickets to get to the ferry. The ferry from Naples to Capri was 45 minutes.

***When taking cabs in Naples, be extremely cautious of being ripped off by the cab driver. Always ask pricing ahead of time and Google Route beforehand so you’re not oblivious of how long it should take.

Just about 11 hours later, we stepped off the ferry in Capri. Honestly, I was completely exhausted from all the travel and really couldn’t wait to get up to the villa. Vito telling me it was their busy season was an understatement as in this very small port, there were at least a thousand people exiting ferries. Vito’s home was situated at the very top of the mountain, seconds from Piazza Umberto.

There’s only 2 ways to get up to the Piazza. One is the Funicular Rail Cart, which tickets must be purchased in advanced of course (and no digital tickets are available). And of course, the line looked like it was at least an hour long. At this point, the New Yorker in me came out and I rolled my luggage out to the road and forced a cab to take me up to the Piazza for 20 Euros. Once in the cab, we were home free. A 10 minute cab ride winding up very narrow roads, with of course, the Italian cab driver cursing at every other driver that passed us.

Low and behold, once we arrived to Vito’s villa, I took a shower and then we went down to the piazza, ordered some coffee and some snacks, and was instantly in Capri heaven. Once I got my bearings and realized what a breathtaking place I was in, Vito took us to his friends hotel where we lounged in the pool, ordered more food, and drank prosecco.

Later on that evening right before sunset, Vito arranged to have his friend take us out on his boat. Just about 15 hours after leaving NYC, I was laying on the front of the boat and drinking Italian beer as we sailed through the famous arches of Capri, Faraglioni. We anchored the boat near the Blue Grotto and swam in the warm Mediterranean water until it was close to sunset while blasting Italian pop music and drinking.

As dinner time in Italy approached (9pm), I was completely exhausted so we just found a small local restaurant, very close to the piazza, that had incredible views and good house-made pastas, seafood and pizza.

After a great night’s sleep, the following day we did the basic touristy stuff: had breakfast in the piazza, did some shopping, lounged by the pool, wandered aimlessly and made a reservation for a 1 Michelin Star dinner at Le Monzù in Hotel Tragara. The only downfall of this dinner is that I made the reservation too late. I highly recommend having dinner here while it is still sunlight as it’s one of the most incredible views of Capri. I would say the service was amongst the best you will find in Capri, it was a very romantic setting, and somewhat reasonably priced for the experience. Instead of ordering one of the Chef Tasting menus, I made a tasting myself by ordering multiple courses off the a-la carte menu. Warning, the portions are much bigger than you would expect, typically of this style of restaurant. To say the least - I definitely over ordered. After a three hour dinner, the 25 minute walk back down to the Piazza through the dimly lit cobblestone pathways was exactly what Nicole and I needed after a huge meal.
**Highlight dishes: Bread Course, Black Truffle Custard, Octopus and Apple, & Zucchini Pasta and Razor Clams.

Against Vito’s recommendations of spending a week in Capri, our trip was a little short. The following morning, Nicole & I were headed to Mykonos. However, Vito was definitely not allowing us to leave the island without a night of partying at the discotheques in Capri. Vito seemed like the mayor of Capri and knew everyone there (and it seemed that he was definitely a regular at the club). We started the night at his favorite cocktail bar where many of his friends joined us, and like typical Italians, it seemed like we all knew each other for years just after a couple of drinks. The club we went to afterwards, was a little different than New York City clubs. One level had a live cover band that put their own spin on American classics. After spending a couple of hours of nonstop dancing on that level, we headed downstairs to check out the house music scene (not exactly my genre of music), but also extremely fun.

At 4am, I had to pull an Irish exit in Italy, get back to the villa, pack my bags, take a short nap, wake up and try to figure out how to get Funicular Rail tickets, followed by ferry tickets to make our flight from Naples to Mykonos. That early in the morning in Capri, most of the island was still dreaming about delicious food and prosecco so it was very easy getting onto the rail cart and ferry. I promised Vito I will be back to Capri and spend at least five days there to see the rest of the island before heading off to explore the rest of the Amalfi Coast.

Grazie per l’ospitalita Vito, ci vediamo a lavo!