O'Leary Travel
Expert Planning
Exceptional Journeys
Thoughtfully Designed European Journeys, Luxury Cruises & Curated Global Travel
Not ready to schedule? Start with a quick inquiry
Why Work With O'Leary Travel
Straightforward planning, honest guidance, and trips that actually feel good to take.
Real Experience
Vetted Partners
Personalized Trips
Honest Guidance
1:1 Planning
Travel Doesn’t Have to feel overwhelming
Travel Doesn’t Have to feel overwhelming
If you’re feeling unsure where to begin, you’re not alone. With so many options, conflicting advice, and endless scrolling, planning a meaningful trip can quickly feel like a second job. That’s where I come in.
I help you clarify your vision, match you with the right cruise, tour, or custom itinerary, and manage every detail from start to finish so your experience feels effortless from the very beginning.
You’ll have a single point of contact, thoughtful guidance, and a plan designed around you not a template.
Not ready to schedule? Start with a quick inquiry
How I Design Your Journey
Every journey begins with understanding and is refined through experience, trusted partners, and intentional design.
1.
Discovery & Direction
We begin with a personal conversation to understand your travel style, priorities, timing, and the experiences that matter most to you. This is where your vision takes shape. If you prefer, you can fill out the basic information on a detailed but each form prior to the meeting.
2.
Curated Design
Using vetted global partners and professional resources, I research and thoughtfully design your itinerary. I work carefully to start placing the outline of your trip, based on your feedback and budget.
3.
Seamless Booking
Once your plan is refined, we book the travel in the way that best serves you. I coordinate all reservations, confirmations, special requests, and documentation on your behalf.
4.
Travel with Confidence
You’re supported before departure and while you’re away. If anything shifts, you have an experienced advocate managing the details for you.
5.
Refine for the Future
After you return, your feedback helps shape future journeys — ensuring each trip becomes even better than the last.
Expert planning. Exceptional journeys
Not ready to schedule? Start with a quick inquiry
O'Leary Travel Services
Custom Travel Planning
Thoughtfully designed itineraries built entirely around your preferences.
Cruises
Ocean, river, expedition, and private yacht experiences
Guided Tours
Carefully selected and curated journeys worldwide
Hosted & Curated Travel
Group trips I personally escort or organize.
Hotel & Resort Bookings
Preferred partner perks, upgrades, and VIP amenities
Group Travel Planning
One organized point of contact for multiple bookings in group
Not sure what type of trip is right for you? That’s exactly what the consultation is for.
Not ready to schedule? Start with a quick inquiry
Expert Planning
Exceptional Journeys
