About Once Upon A Trip Travel

Our Story, Your Adventure

Meet the founder behind Once Upon A Trip Travel and the passion that fuels every itinerary.

Team Spotlight

Meet Our Founder

Once Upon A Trip Travel is built on a small team of advisors who plan from firsthand experience, not a script. Each specialist brings a distinct area of expertise, so every itinerary is guided by someone who has genuinely done the research.

Rhonda, co-founder of Once Upon A Trip Travel, wearing a red heart-print shirt
Rhonda, co-founder of Once Upon A Trip Travel, standing near a white building
Rhonda, co-founder of Once Upon A Trip Travel, next to the iron Mickey Mouse sculpture
Rhonda, co-founder of Once Upon A Trip Travel, smiling

Rhonda

Co-Founder & Travel Advisor

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Ava, co-founder of Once Upon A Trip Travel, smiling portrait

Ava

Co-Founder & Travel Advisor

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Meet the Team

The People Behind Every Itinerary

Every advisor on our team plans from firsthand experience. Get to know the people who will help design your next trip.

Chelsie, travel advisor at Once Upon A Trip Travel, smiling

Chelsie

Travel Advisor

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Lucas, travel advisor at Once Upon A Trip Travel, smiling portrait

Lucas

Travel Advisor

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Dana, travel advisor at Once Upon A Trip Travel, smiling

Dana

Travel Advisor

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CJ, travel advisor at Once Upon A Trip Travel, smiling headshot

CJ

Travel Advisor

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Rhonda, founder of Once Upon A Trip Travel, smiling and gesturing toward a scenic bridge
Our Founder

From Wanderer to Trusted Advisor

Once Upon A Trip Travel began not in an office, but on the road — across airport terminals, cruise ship decks, and winding family road trips that never quite went as planned. Our founder spent years chasing the same question every traveler eventually asks: why does planning a trip feel harder than actually taking one?

That question turned into a career. What started as a personal passion for exploring new destinations with family in tow grew into a deep understanding of how the travel industry really works — where the hidden costs live, which resorts deliver on their promises, and how the right itinerary can turn a good vacation into a lifelong memory.

Today, that firsthand experience is the foundation of every itinerary Once Upon A Trip Travel builds. Families planning their first big vacation, cruisers chasing their next horizon, and travelers who simply don't want to plan alone all benefit from the same lesson learned one trip at a time: the best journeys are guided, not googled.

Firsthand Experience

Advice Rooted in Real Travel, Not Guesswork

Understanding the core components of personalized planning starts with having lived them. Before Once Upon A Trip Travel ever books a family's itinerary, that itinerary has already been tested — at sea, at the resort, and everywhere in between.

White ship on the sea during sunset

20+ Ocean Cruises Completed

From Caribbean escapes to transatlantic crossings, our founder has personally sailed more than twenty ocean cruises — testing cabin categories, dining rooms, and shore excursions before ever recommending them to a client.

Brown and white railings near body of water aboard a family cruise

Countless Family Vacations

Planning a trip for a family is different from planning one for a couple. Years spent traveling with children of every age has shaped an approach built around real logistics, not guesswork.

White and blue ship on the sea under white clouds during daytime

Firsthand Destination Immersion

Resorts, ports, and itineraries are walked and evaluated in person before they're placed in front of a client — so every recommendation comes from experience, not a brochure.

Our Philosophy

A Philosophy Built on Personal Care

Boutique travel planning means something specific at Once Upon A Trip Travel: a small, dedicated advisory focused on families and vacation travelers, not a call center working through a script. Understanding the core components of personalized planning — from cabin category to shore excursion pacing — produces a seamless travel experience that off-the-shelf booking sites simply cannot replicate.

Father and daughter looking at an airplane together at the airport gate

Curated, Not Cookie-Cutter

Every itinerary begins with a conversation, not a template. Once Upon A Trip Travel builds each family and vacation plan around the traveler's pace, budget, and priorities — not a one-size-fits-all package.

Relationships Over Transactions

A trip doesn't end when the booking confirmation arrives. Clients work with the same trusted advisor from first inquiry through final send-off, building a relationship that carries into every future adventure.

Insider Access, Real Value

Years of firsthand cruise and resort travel, paired with established supplier relationships, translate into perks, upgrades, and pricing that families and independent travelers can't secure planning alone.

Beyond the Booking

Mentoring the Next Generation of Travel Advisors

Long before founding this agency, our founder was the friend everyone called for vacation advice. That same instinct to teach and guide now extends to aspiring travel agents who want to turn their love of travel into a meaningful career. Mentorship here isn't a side offering — it's part of how this agency was built.

Each new agent is paired with hands-on coaching rooted in real experience: firsthand cruise planning, family vacation logistics, and the relationships that make an itinerary feel effortless. It's mentorship built on lived expertise, not a script.

Hands-On Guidance

New agents learn directly from a founder who has booked hundreds of family vacations, cruises, and all-inclusive getaways — not from a generic training manual.

A Real Growth Path

From your first booking to building a steady client base, mentorship is structured to help aspiring agents grow at a pace that fits their goals.

A Supportive Community

Agents mentored under Once Upon A Trip Travel stay connected for ongoing support, shared resources, and encouragement long after onboarding.

A group of aspiring travel agents sitting together at a table during a mentoring session

Why Families Trust Our Guidance

Every itinerary starts with a relationship. Here's what clients say about working with a founder who plans travel the way she'd plan it for her own family.

"From the very first call, it was clear our advisor understood exactly what our family needed. She handled every detail of our all-inclusive booking and even caught a resort policy that would have affected our kids' room. That level of care is why we'll never plan a vacation on our own again."

Portrait of Melissa R.

Melissa R.

Charlotte, NC · Family All-Inclusive, Riviera Maya

"We had booked cruises ourselves for years and always felt like we were missing out on the best cabins and perks. Once Upon A Trip Travel secured an upgraded stateroom and onboard credit we didn't even know to ask for. Their firsthand cruise experience made all the difference."

Portrait of David T.

David T.

Columbus, OH · 7-Night Caribbean Cruise

"What stood out most was the honesty. Our advisor told us plainly which package was worth the extra cost and which wasn't, even when it meant a smaller commission for her. That kind of guidance builds real trust, and it's why our whole extended family books through her now."

Portrait of Priya K.

Priya K.

Austin, TX · Multi-Family Vacation Package

Let's Start Planning Your Story

Reach out today and let our experience guide your next unforgettable trip.