For most, the gentle rhythm of a ship sailing across the Caribbean or the sounds of the coastal breeze through the sunlit streets in Greece are passing daydreams of escape. But for Jeffrey Leonardi, they’re a part of his life’s calling. A career shaped by curiosity, perseverance, and the belief that crafting experiences is a profession to be honored, all wrapped together in his travel agency, Travel Time Vacations.
Leonardi has spent decades mastering the craft of creating seamless, soul-stirring journeys for his clients. His passion began as a teenager in the 1970s, living across the street from a small travel agency. “It was run by a mother-daughter duo. They took me under their wing and trained me extensively,” he recalls. “I worked with them through high school, and they taught me computer reservation systems. I was hooked.”
That early exposure became the impetus for what would become his lifelong pursuit, though his path would take many detours first. Leonardi studied at a renowned acting school in New York and later at a musical academy in London before moving to Hollywood, where he became a talent agent. After developing a rare blood disease, the fast-paced stress of show business took its toll on him. “It was time to step away,” he shares. “My family nursed me back to health, and in that time, I rediscovered my passion for travel.”
Within six months of making a simple booking for his mother’s birthday, Leonardi purchased the agency that helped him plan the trip, and eventually, acquired four more agencies in the area. Today, Travel Time Vacations is a testament to resilience and passion, offering everything from bespoke family vacations to luxury cruises that sail through Europe and North America’s most enchanting oceans and waterways.
Leonardi doesn’t call himself just a travel agent. “For me, this is a profession. I’m an advocate for my clients. I cross every ‘T’ and dot every ‘I.’ I handle everything from the moment they book until they return home,” he shares. This meticulous approach begins with a detailed itinerary he crafts as soon as clients book with him, whether it’s a Mediterranean cruise or an Italian countryside tour. It is created with a keen eye for detail and an ear for what the traveler truly wants.
Encompassing flights, hotels, escorted tours, and cruises, Leonardi ensures that every element within the itinerary fits together synergistically. “There’s no service charge when everything is booked through me,” he reveals. “We do it all simply because we want to enhance the experience comprehensively for our clientele.”
Leonardi’s reach is global, but his roots run deep between North America and Europe. With dual citizenship in the US and Italy, he’s built a network of connections that allow him to curate authentic experiences and secure exclusive arrangements. “When it comes to Europe, I have so many contacts, it’s unbelievable,” he shares. “But my biggest priority remains on making sure my clients feel they’re in good hands, no matter where they go.”
Leonardi’s credibility in the industry is further cemented by his affiliations with respected travel organizations. These partnerships are designed to give him access to global networks and ongoing educational programs, ensuring that both Leonardi and his agency remain at the forefront of travel industry standards.
His commitment extends to every vacation he plans, strengthened by his specialty not only in both ocean and river cruises, but vacations of any kind. He favors luxury liners that prioritize experience over excess. “I want travelers who value the journey as much as the destination,” he shares.
During the pandemic, Leonardi’s adaptability kept Travel Time Vacations afloat. “My clients still wanted to travel,” he recalls. “They just needed options closer to home.” Instead of stopping his operations, he pivoted to domestic river cruises within the US, many sailing from Portland, Oregon, to Lewiston, Idaho. During this time, Leonardi also arranged domestic vacations. “That flexibility saved us,” Leonardi adds.
Travel Time Vacations continues to craft journeys that are rooted in transformation, from stepping into the glow of Santorini’s cliffs to sailing in the serene canals of Venice. Leonardi shares, “It’s a joyful business, but at its core, it’s about something deeper: bringing happiness, creating memories that linger long after the journey ends. And when that happens, there’s no feeling quite like it.”
