[§] Where it actually runs
I own Caballeros Vacations, a full-service travel agency. Most of what we book is family travel: vacations where what matters is the kids' first beach and the in-laws' flight not getting split. When something goes wrong on a Tuesday, I'm the one on the phone with the resort.
[§ 01]
How I think about it.
Caballeros Vacations
My travel agency
Travel isn't a discipline I consult on from the sidelines. It's one I happen to operate a business in. That means the reflexes are different. I know which OTA bookings actually save money versus which ones come back to bite. I know what to do when a hotel block falls apart at 9pm. I know which all-inclusive resorts pretend to be one tier and operate like another.
Most of the work is family travel. Honeymoons, first-time-Disney parents, in-laws who need adjacent rooms, four kids who all need their own boarding pass. The trips where matching the experience to the family matters more than chasing the lowest fare. Group and corporate travel are also part of what I book. They're welcome when they fit, but family is what shows up most weeks.
Most travel agencies sell you a trip. I run an agency, so I sell you the operations behind the trip.
[§ 02] What the work actually builds
Running an agency is a logistics, sales, and vendor-management job that happens to end in a vacation. Here is the muscle it builds, the part that carries over to any operation where the details have to land and someone has to own the outcome.
01
I book direct with resorts, cruise lines, wholesalers, and tour operators, not through a faceless portal. Years of it means I know which properties deliver and which oversell, and I have the relationships to get a real person on the phone when a room block falls apart the night before arrival.
02
A multi-generation trip is a dozen travelers, a stack of flight itineraries, room blocks, transfers, excursions, and dietary notes that all have to land on the same day in the right order. I plan it with a fallback for every piece, because the cost of a dropped detail is someone's once-a-year vacation.
03
Closing the booking is the easy half. The harder half is matching the right trip to the right people, pricing it honestly, and being the one who picks up when something goes sideways mid-trip. Every sale is a promise I keep personally.
04
The same muscle with more on the line: more travelers, tighter timelines, a client accountable to their own team. Conferences, offsites, incentive trips, milestone group travel. Family work is most of the volume, but the corporate door is open, and it runs on the same vendor relationships and the same reflexes.
[§] Trusted to teach it
Platforms in the travel industry bring me in to train other agents. For Travefy I led a sales webinar on using upsells to build a better trip, the kind a client actually thanks you for. Through mExperts I've run resort training webinars, including for the Iberostar Paraiso complex. When a platform wants someone to teach its own agents, that is the read on where I sit in this industry.
[§ 03] What I actually book
From
NYC
To
CUN
[§] Class · Family Vacations
All-inclusives, beach weeks, first-trip-with-a-toddler logistics, multi-gen with grandparents and grandkids on the same property. Most of what Caballeros books, and what we know best.
From
NYC
To
MCO
[§] Class · Theme Parks & Cruises
The trips with a lot of moving parts: park tickets and dining reservations, cruise excursions, accessible rooms when needed. Booked through agency channels that get perks and protections most direct bookings don’t.
From
NYC
To
PUJ
[§] Class · Group & Corporate
Multi-family group trips, milestone vacations (anniversaries, big birthdays), and the occasional corporate engagement when the team is small and the trip matters. Welcome but not the primary lane.
Issued by · Caballeros Vacations · NYC · MMXXVI
[§ 04] Where families actually go
[§ 05] How it connects
Caballeros runs on a stack I built and operate. Web forms feed leads into automation. AI handles afterhours inquiries. Marketing campaigns drive bookings. When I work with another business on those layers, I'm not theorizing. I'm doing it on my own books, every day, where the cost of being wrong is my own revenue.
[§] Plan a trip
Send a short note: who's traveling, when, rough destination, and what the trip needs to feel like. We'll come back with options and honest pricing. Corporate or group trip? Same email works.