Caitlin & Positano

Caitlin Humphreys in Boat in Italy
Exploring by sea
Caitlin and Wendy hiking in Positano Italy
Hiking the Almalfi Coast
Positano Italy at Night

San Pietro - Darren and Caitlin Humphreys
At Il San Pietro, 2019
View from villa in Positano
View from the villa
View of Church in Positano

Caitlin in Italy
In Positano, 2019

Caitlin & Positano…

My First Foray

by Caitlin

Circa 2007, I disembarked from the plane in Naples, Italy with a backpack of heavy legal books.  I had recently transferred from the Boston to New York office of my law firm and I had the summer off to study for the New York bar exam.  My friend Wendy came running up to greet me with a wild look in her eyes and grin plastered across her face.  “You are not going to believe this…” she began as she led me out to the waiting limousine service (Not the norm for us at this time!  We were still paying off loans and hitting two-for-one happy hours).  

Caitlin and Wendy in Positano
Caitlin and Wendy – Positano, 2007

Wendy had arrived at our shared villa in Positano a week before me.  Adept at languages, she was already speaking half English and half Italian and had befriended the locals.  The limousine was owned by her new friend Luigi of Positano Limousine Service.  Wendy frenetically told me about her adventures thus far on the winding ride to Positano and before even going to our villa (which was half way up a staircase-only accessible mountain…I left that summer with thighs of steel!) we went to the beach.  Not just the beach, but the “VIP beach”, La Scogliera, at the very end of the strip where the locals frequented.  Luigi and his friends Christian, et al., greeted us “Ciao bella!” and prosecco swiftly arrived in ice buckets.  

Caitlin and Wendy Positano
At La Scogliera

Our local friends showed us the best restaurants, told us what to order (squid aqua pazza will forever be my favorite), showed us the coast via boat, and took us dancing at the club Music on the Rocks (fondly known as “Musique”) at night.  Wendy and I found our own adventurous hikes during the day (with our share of run-ins with wild cats and dogs…) and did the “touristique” visits to surrounding towns and Capri.  We learned which beach changing rooms the local boys had peep holes into and which men were the playboys of whom to be wary.  Wendy played soccer with the locals and answered the phones at Positano Limousine Service.  Oh, and I managed to study some and pass the New York bar….

Jumping off cliff in Positano
Getting ready to jump

Fast forward from that memorable summer…the Amalfi Coast pulled Wendy and I back, both independently, together and with many friends, over and over (and still does).  Wendy ended up marrying Pasquale from Praiano (a town nearby Positano) and they have two children – Daniela and Cameron.  I returned to Positano many times alone and had rich experiences with the locals, including “accidentally” missing my flight and having gracious friends host me, attending a 50th birthday party at the Buca di Bacco where I was the only one who did not speak Italian (and thus did a lot of polite nodding!), taking many boat rides to “locals only” restaurants with my friend Giancarlo, and sharing pasta with Chef Alois Vanlangenaeker and Vito Cinque (San Pietro).  In the last decade, I have been back to Positano many times, but as a guest staying at the finest hotels rather than backpacking hundreds of steps up a mountain to my villa, although still seeing the same local friends.  Many of these friends have become supremely successful and it is a pleasure to be able to send clients their way (View our article on Zass).

I cannot decide whether Positano touched my heart more in 2007 or now, but as John Steinbeck said, “Positano lies deep.  It is a dream place that isn’t quite real when you are there and becomes beckoningly real after you have gone.”  I will forever keep going back, and I hope you do too.