Meet Erin O'Leary

Travel has always been more than a vacation for me — it’s how I reset, reconnect, and rediscover what matters. The wonder of new places bring me joy and awe.

Long before I founded O’Leary Travel, I was someone who planned trips with care and intention: thoughtfully paced itineraries, hotels that felt just right, and experiences that made a destination come alive. What began as a personal passion eventually became a profession — one rooted in listening closely, anticipating needs, and creating experiences that feel effortless from start to finish.

I began my professional career as an attorney, earning my undergraduate degree from Pennsylvania State University and my law degree from Rutgers School of Law. I went on to serve as a Deputy Attorney General, then Assistant Attorney General for the State of New Jersey, a role that sharpened my attention to detail, advocacy skills, and ability to manage complex situations with calm and clarity.

While my career path has evolved, those skills remain central to how I plan travel today — thoughtful preparation, clear communication, and always looking out for my clients’ best interests.

Why I Do This

I believe travel should feel exciting — not overwhelming. My role is to help travelers clarify their vision and match them with the right cruise, tour, or custom itinerary, while managing the details behind the scenes.

Whether it’s a milestone trip, a long-awaited getaway, or a thoughtfully planned escape, I focus on creating journeys that feel seamless, well-paced, and personal.

And I love the joy travel brings all people.

Hosted Travel Experiences

In addition to custom trip planning, I host a select number of small-group trips each year.

These journeys are designed for travelers who want the ease of having everything arranged — without feeling rushed or over-scheduled - and maybe for those looking to join a group of travelers instead of going it alone.

Examples of trips I’ve hosted include:

A winter Iceland land tour, focused on natural wonders and seasonal experiences
A European cruise from Venice to Rome, including Croatia and the Amalfi Coast
Paris small-group travel, designed as an elegant long weekend
A curated Ireland tour, blending culture, history, and local flavor
A Croatia yacht cruise, combining coastal exploration with relaxed luxury

Each hosted trip is intentionally small and personally hosted by me, with a focus on connection, comfort, and meaningful experiences.

{View upcoming hosted trips — LINK PLACEHOLDER]

Hosted Travel Experiences

In addition to custom trip planning, I host a select number of small-group trips each year. These journeys are designed for travelers who want the ease of having everything arranged — without feeling rushed or over-scheduled - and maybe for those looking to join a group of travelers instead of going it alone.

Examples of trips I’ve hosted include:

A winter Iceland land tour, focused on natural wonders and seasonal experiences
A European cruise from Venice to Rome, including Croatia and the Amalfi Coast
Paris small-group travel, designed as an elegant long weekend
A curated Ireland tour, blending culture, history, and local flavor
A Croatia yacht cruise, combining coastal exploration with relaxed luxury

Each hosted trip is intentionally small and personally hosted by me, with a focus on connection, comfort, and meaningful experiences.

{View upcoming hosted trips — LINK PLACEHOLDER]

A Few Things You May Not Know About Erin

I love solo travel — it’s often where I feel most grounded and I can be fully myself.

My favorite city in the world is Paris. I’ve returned many times, and it still feels endlessly rewarding.

My favorite trip of all time was exploring the Galápagos Islands — a truly unforgettable experience that reshaped how I think about travel and nature.

I was born in California, but I’m a Jersey girl at heart.

I live in gorgeous, historic Lambertville, New Jersey, a place that mirrors so much of what I love: walkability, character, and a strong sense of community.

Before travel became my full-time focus, I argued cases more than once before the New Jersey Supreme Court — an experience that taught me confidence, preparation, and how to stay calm under pressure.