Meet Matt
The story behind the itinerary
Matt Feldman
I Plan Trips That Last a Lifetime
At 21, I boarded a cruise ship as part of Semester at Sea and spent a semester circling the globe, taking classes on board and stepping into countries I had only read about. That voyage rewired how I see travel. It stopped being about checking boxes and became about disappearing into a place — finding the restaurant where only locals eat, the bar that does not have a sign, the street musician playing at midnight.
Since then, I have traveled internationally every single year. Friends started asking me to plan their trips. Then their friends did. I became the person who gets a text that says “We have 6 people, 10 days, and we want to do Japan” and comes back with a day-by-day itinerary that makes the whole group feel like VIPs.
The Day Job
Tech Executive. Operations Obsessed.
I am a founder and Chief Operating Officer in the software and tech industries. I work with AI and emerging technologies every single day — building systems, optimizing workflows, and solving complex problems at scale. That same operational mindset goes into every itinerary I build: contingency plans, timing buffers, backup reservations, seamless transfers.
I am applying this tech-forward approach to enhance what I offer as a travel agent. Using tools like Claude, I build custom, interactive itineraries that can cover as much or as little detail as you want — from high-level day plans to hour-by-hour breakdowns with restaurant menus, walking routes, and backup options for rain days. Your itinerary is not a PDF. It is a living, personalized guide.
Premium Add-On
White Glove Service
Want someone to handle absolutely everything? For an additional fee, I offer white glove concierge services — I will personally book your restaurant reservations, spa appointments, massages, special events, private tours, and anything else that makes your trip seamless. You show up and enjoy. I handle the rest.
“Just tell me what kind of experience you want. I will make it happen.”
The Soundtrack
Music & Live Events Run Through Everything
I am a musician and I average about one live event per week. Music and live events are not just hobbies; they are how I experience a city. Whether it is a blues bar in Chicago, a jazz club in Tokyo, a sold-out arena show, a multi-day festival, an industry conference, or a comedy showcase — I know how to build a trip that puts the event at the center and fills in the rest with world-class food, nightlife, and culture.
The Portfolio
Places That Shaped the Way I Travel
The Wave, Arizona
Vermilion Cliffs National Monument
Slot Canyon
American Southwest
The Narrows
Zion National Park, Utah
Pamplona, Spain
San Fermín Festival
Medellín, Colombia
The City of Eternal Spring
Officially Licensed
I recently joined HOTE Travel as a licensed travel agent, which means I can now offer these curated experiences professionally — with full booking support, exclusive rates, and the peace of mind that comes with working with a licensed advisor. This is not a side hustle. This is what happens when 15 years of obsessive travel planning meets a professional platform.