Tommy Pescatore

Specialties

Tommy designs bespoke milestone and destination celebrations that masterfully balance adventure with serene relaxation.

With a background in engineering and corporate finance, Tommy brings a uniquely detail-oriented and analytical approach to curating travel experiences. What began as a passion for helping friends plan their honeymoons and complex multi-city itineraries soon blossomed into him following his calling as a travel advisor, building seamless, stress-free journeys for discerning clients.

Tommy’s love for travel is rooted in immersing himself in new cultures, savoring local cuisine, and connecting with people across the globe. For him, the right hotel is never just a backdrop; it is the element that transforms a trip from great to truly unforgettable, seeing out properties that go above and beyond in service and atmosphere alike, in turn, creating the kind of memories that last a lifetime. When designing a trip, Tommy’s top priority is to align each itinerary with his clients’ unique personalities and desires. He dedicates time to understanding what excites them, then crafts journeys that maximize value while weaving in thoughtful, memorable touches.

Based in South Florida, Tommy enjoys exploring luxury getaways with his wife. His personal travel style favors a perfect rhythm of sightseeing and relaxation—a philosophy that shapes every recommendation he makes, ensuring each journey feels impeccably tailored, joyful, and restorative. Ultimately, for Tommy, it’s about seeing his clients return home with extraordinary stories, meaningful connections, and moments they will cherish forever.

What has been your most memorable travel experience to date?

It’s difficult to choose just one because my most cherished memories are so different from one another. Experiencing the overwater bungalows in Bora Bora was a dream come true, waking up to a French press coffee as the sun rose over the turquoise water with Mount Otemanu in the background. The view was so breathtaking it felt like living inside a screensaver. More recently, I’ve had unforgettable moments like attending my first Champions League match in Madrid alongside my brother, and hearing Taylor Swift perform London Boy in London with my wife—we’re big-time Swifties, so that was truly special. Each of these experiences represents what I love most about travel: the chance to create once-in-a-lifetime memories that stay with you forever.

Which destinations are you looking forward to visiting? Why?

I’m especially looking forward to my upcoming trip to Japan. As a foodie, I can’t wait to dive into the country’s culinary scene, from savoring some of the world’s best sushi to exploring its rich traditions and vibrant culture. Japan’s diversity fascinates me, from bustling city life to tranquil temples and natural beauty. As an avid skier, I’m also excited to experience the legendary powder snow in Hokkaido and warm up with a bowl of steaming ramen right from the slopes. It’s the perfect destination to blend my love for food, culture, and adventure into one unforgettable journey.

Travel Tip

  • Don’t be afraid to step out of your comfort zone. Order the dish you can’t pronounce, try the experience that feels a little unfamiliar, and let the destination guide you. Travel is about more than seeing new places, it’s about tasting, living, and discovering sides of yourself you never knew were there.