You have to love a father who names his son Ulysses. My friend Sergio and his opera-singer wife christened their only child in honor of history’s most epic traveler. “They wanted to embed wanderlust in me,” laughs Ulysses. When I asked Sergio if it was true, he confirmed the family tale with a trademark mustachioed smile that his fan club of Classic Journeys guests would recognize instantly.

Almost 25 years ago, Sergio met us in his native Naples to scout our very first Classic Journeys’ trip to the Amalfi Coast. In our debut year, Amalfi was one of just six itineraries we offered. Every year since, it’s been one of the most popular trips, and Sergio has been with us all the way. As a teenager, Ulysses (his name is Ulisse in Italian, but he prefers the English pronunciation) interned in our office in California. Over the last 16 years, we were almost as proud as his father to watch him become an accomplished guide for several companies, one of which named him their European tour leader of the year multiple times. He’s been one of our most popular local guides for a decade or so, and with the upcoming birth of his first child, we like to think the third generation is on the way!

Sergio & Ulysses overlooking harbor in Naples

“It’s wrong to call this a job,” Ulysses insists. “Every day, I wake up happy for another chance to show guests around the places and the secret corners where I live and where I grew up.” As for Sergio, I suppose that at some point in history, he met a stranger. But I’ve never seen evidence that there’s anyone he doesn’t know in his native Naples, Capri or Positano. He makes it sound deceptively simple: “I’m lucky to have many friends. Many have known Ulysses his whole life. Our friends are your friends, too.”

The depth and sincerity of their ties have blown us away again and again. None of the guides that other companies shuttle in from the U.S. or Canada — no matter how gung-ho or well-versed in guidebook facts — can match their connectedness. For proof that it’s not what you know, it’s who you know, look no further than a family house that sits on a cliff above Praiano.

View from hills of the Amalfi Coast

For generations, the family that lives in that house worked the land for the monastery that’s even higher up the slope. The monks are gone now, but the family remains, tending their terraced vineyards and gardens. All Classic Journeys guests know this because — thanks to the good graces of Sergio and Ulysses — the family invites you to lunch after you meet the artisans who are restoring the monastery’s frescoes.  Signora Grazia will wave you out to the terrace where you can see Positano and all the way to Capri. Over at the barrel of “grape juice” (aka homegrown wine), you’re instructed to twist the spigot and fill your glass as often as you like. In the cave built into the cliff behind the house, there’s a disk of pizza dough for you to stretch, top to your taste, and bake in the wood-fired oven. Lunch on that terrace as you chat with the family and soak in the view is some kind of heaven — a deeply authentic moment that no tourist can experience at any price.

The greatest gift you can receive as a traveler is the rare thrill of feeling at home in a place that couldn’t be farther from your everyday life. From the first “Ciao!” you hear from Ulysses or Sergio, you’ll feel that great sense that you are right where you belong. When you visit the Amalfi Coast with Classic Journeys, you become an instant part of the extended family they have created … and add an unforgettable chapter to your own lifelong odyssey.

Group on a hike in the Amalfi Coast

LOCAL MATTERS
When you compare tours, be sure to ask if your guide will be a native of the place you’re visiting. All guides on all of our trips are locals. They have deep roots in the region that assure you a very personal, totally plugged-in view of the people and culture you’re there to discover. A lot of them have been a part of the Classic Journeys family for 10 years, 20 years and even longer. Many operators tout the guides they import from around the world on their Instagram feeds. Nice and well-intentioned they may well be, but if your goal as a traveler is to get the most immersive feel for a place, local truly matters!