Trusted Partners
These are travel partners I trust and regularly recommend — companies that align with my approach to planning: quality experiences, reliable execution, and thoughtful design. Each partner below plays a different role in creating a seamless trip.
Tours & Shore Excursions
Viator
Global Tours & Activities
A worldwide marketplace of guided tours, activities, and shore excursions — from private walking tours to skip-the-line museum access and food experiences. Viator is ideal for adding flexible, well-reviewed experiences to independent travel or cruise itineraries.
Project Expedition
Curated Local Experiences
Project Expedition specializes in high-quality, vetted tours led by local operators. Their experiences often feature smaller groups and more immersive options, making them a great choice for travelers looking to go beyond the basics.
Tauck
Premium Guided Tours & River Cruises
Tauck is known for expertly guided land tours and river cruises with strong storytelling, seamless logistics, and special access. A great choice for travelers who want depth, comfort, and consistently high standards.
Cruise Partners
Explora Journeys
Modern Luxury Ocean Cruising
A refined, all-suite ocean cruise experience focused on space, design, and well-being. Explora Journeys is ideal for travelers who want the ease of cruising with a calm, elevated onboard atmosphere and immersive destinations.
Silversea
Luxury & Expedition Cruising
Silversea is known for intimate, all-inclusive luxury cruising, with spacious suites, personalized service, and destination-focused itineraries. From classic ocean voyages to expedition cruises in places like Antarctica and the Galápagos, Silversea is ideal for travelers who value comfort, enrichment, and immersive exploration.
Norwegian Cruise Line
Flexible & Contemporary Cruising
Known for its relaxed “Freestyle Cruising” style, Norwegian Cruise Line offers flexibility in dining, entertainment, and itineraries. A strong option for travelers who value choice, variety, and a more casual onboard experience.
Expedition Cruises
National Geographic Expeditions
Expedition & Expert-Led Travel
National Geographic Expeditions offers immersive, expertly guided journeys led by scientists, naturalists, and subject-matter experts. These trips emphasize education, conservation, and deep destination insight — ideal for travelers who want to understand the places they visit, not just see them.
Viking River Cruises
Destination-Focused River Cruising
Viking River Cruises offers culturally immersive journeys along Europe’s most iconic rivers, with thoughtfully designed itineraries, included shore excursions, and an adults-focused onboard atmosphere. It’s ideal for travelers who enjoy history, learning, and a relaxed, well-paced river cruise experience.
Travel Insurance & Protection
Travel insurance is an important part of protecting your investment — and your peace of mind — before and during your trip.
Coverage can help safeguard you against unexpected events such as trip cancellations or interruptions, medical emergencies, travel delays, lost or delayed baggage, and more.
Many plans also offer options for cancel-for-any-reason, medical evacuation, and pre-existing condition waivers, depending on timing and coverage level.
While insurance is never required, it is strongly recommended, especially for international travel, cruises, and custom itineraries where deposits and supplier penalties may apply.
Below are trusted travel insurance providers I recommend. Clicking an icon will take you directly to each company’s site to review plans and request a quote.
You are always welcome to ask for guidance on choosing coverage that fits your specific trip.
(Travel insurance is offered through third-party providers. O’Leary Travel does not sell or underwrite insurance but is happy to provide guidance based on your itinerary.)
Medical Transport & Evacuation Membership
Medjet is not traditional travel insurance — it is a medical evacuation membership designed for travelers who want control over where they are treated if a serious medical event occurs while traveling.
If you are hospitalized more than 150 miles from home, Medjet arranges and covers transport to the hospital of your choice — whether that’s closer to home or a preferred medical facility — once you are stable to travel. This service complements (but does not replace) travel insurance or medical coverage.
Medjet is especially valued by travelers taking international trips, cruises, long stays, or remote itineraries, and by those who want peace of mind knowing they won’t be required to stay in a foreign hospital.
