Jon Herlihy

Jon has been absolutely exceptional in helping me and my family plan several of our recent trips, including stays in Ireland, Chicago, and New York City. Every experience he’s crafted for us—from finding beautiful hotels in ideal locations to securing truly stunning rooms—has exceeded our expectations.

What sets Jon apart is not just his talent for finding top‑notch accommodations, but the thoughtful, comprehensive way he approaches each trip. He goes above and beyond by helping us plan meaningful activities, whether it’s arranging Broadway show tickets, offering restaurant recommendations we end up loving, or mapping out daily itineraries that make each destination feel both enjoyable and effortless.

Because of how positive our experiences have been, we’re already working with Jon again for our upcoming October vacation to Italy. There is something incredibly reassuring about having someone who understands your travel style, anticipates your needs, and consistently delivers an unforgettable experience.

I can’t recommend Jon highly enough—his expertise, attention to detail, and genuine care make every trip feel special.

Incredible. Extremely knowledgeable, friendly, and top notch service.

Jon helps you keep travel booking simple by being highly responsive, presenting clear choices + tradeoffs, and being honest about where he can provide a value or advantage vs where you may get a better deal on certain components of your trip by booking on your own. I've come to trust Jon as an advisor for bookings big and small - he always suggests things you may not have thought about, making you feel like you're working with a pro. And in many cases, working with Jon vs booking on my own hasn't cost me a penny more. For example, as a Marriott Titanium Elite member, my Marriott rates and Jon's rates are often on par but Jon's benefits top my own (better on-property credits, priority for upgrades, welcome gifts, etc.) AND I still earn my points and night credits with Marriott when booking with Jon. This means booking with Jon has always been 100% upside for my partner and I.

Booking with Jon Herlihy for my Napa Valley trip was the best decision I could have made! Jon was attentive, responded quickly, and was very knowledgeable about the property and area I was staying in. Jon booked my accommodations, which included a ton of extra great perks such as early check-in, resort credit, and daily breakfast at the restaurant which was outstanding. Jon made sure I had everything I needed in the weeks and days of my trip. He had a welcome gift waiting for me in my room upon arrival which was such a sweet surprise, it was a great bottle of wine and a crudités platter. Jon also helped me arrange my chauffeur service, and the company he recommended was top-notch. I can’t thank Jon enough for his expertise, professionalism, and dedication to making this a great experience for me. I will be booking with Jon again for my future trips.

We had the pleasure of working with Jon to book our recent cruise with Virgin Voyages, and we couldn’t be more impressed with his service. From the moment we reached out, Jon was incredibly attentive and knowledgeable, guiding us through the entire process with ease. He answered all our questions, provided valuable recommendations, and made sure we had everything in place for a smooth booking experience.

Jon’s personalized approach made us feel confident and excited about our trip. He was always available to assist with any concerns, ensuring that we were well-prepared and well-informed every step of the way.

Thanks to Jon, our cruise with Virgin Voyages was absolutely unforgettable. We highly recommend him to anyone looking for a reliable and professional travel agent who goes above and beyond!