Jon Herlihy
He/Him
Based in Bay Area & Boston
Jon Herlihy
Ask me about
My Story
If travel planning were an olympic sport, I’d be going for gold. For 15+ years I obsessed over the details as a Marketing Director in Tech, and now I’m taking my passion for travel full-time.
My Travel Style
Once I have a destination in mind, I map out the top sites and activities, best hotels, and of course, restaurants. I choose hotels based on central location, value (price & perks) and unique experiences they offer. My ultimate city travel day: free breakfast at the hotel — then off to explore museums, cafes, and...the unexpected. Meet up with old friends for dinner or a show, and top it off with a nightcap in the lobby bar. Ultimate beach vacation? Watching the waves with a coconut drink in one hand and a mystery book in another.
Contact me if you have an upcoming trip and want to explore how to travel like a pro.
Stay connected
My reviews (14)
Sidney B.
19 days ago
Incredible. Extremely knowledgeable, friendly, and top notch service.
Jonathan C.
3 months ago
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.
Kai K.
8 months ago
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.
Melissa L.
9 months ago
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!
Maria M.
9 months ago
There is no one better than Jon Herlihy when it comes to helping our family determine our travel plans. He takes the time to get to know his clients both personally and professionally and provides us with several luxurious (or more reasonable) options depending on our preferences! His love of travel proves to also be a huge help to me when thinking of destinations for myself and my husband as well because we can always trust his recommendations and beautiful photos he posts and shares with his followers. We head to Europe this summer and can’t wait to visit the hotels he has booked for us! Jon is one of a kind and we are so lucky to have found him.
Sidney B.
19 days ago
Incredible. Extremely knowledgeable, friendly, and top notch service.
Jonathan C.
3 months ago
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.
Kai K.
8 months ago
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.
Melissa L.
9 months ago
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!
My travel ideas (3)
Planning a Destination Wedding on Cape Cod
Cape Cod is a summertime hot spot for locals and tourists alike, but it’s also a booming wedding destination for couples from all over the world. Known for its historic cottages and picturesque shoreline, a destination wedding on the Cape provides endless options for fun activities for your wedding weekend.
Planning a Destination Wedding on Cape Cod
Cape Cod is a summertime hot spot for locals and tourists alike, but it’s also a booming wedding destination for couples from all over the world. Known for its historic cottages and picturesque shoreline, a destination wedding on the Cape provides endless options for fun activities for your wedding weekend.
Summer in Boston
Boston is one of the most dynamic and exciting cities to visit in summer. Steeped in history and culture, Boston is walkable and tourist friendly. From world-class museums and sports teams to sunset cruises on Boston Harbor, there is so much to do in Boston in the summer, you might not even make it out for day trips to Cape Cod, Rhode Island, Vermont, New Hampshire or Maine.
Summer in Boston
Boston is one of the most dynamic and exciting cities to visit in summer. Steeped in history and culture, Boston is walkable and tourist friendly. From world-class museums and sports teams to sunset cruises on Boston Harbor, there is so much to do in Boston in the summer, you might not even make it out for day trips to Cape Cod, Rhode Island, Vermont, New Hampshire or Maine.
Complete Three Day London Itinerary
No matter how many times you’ve been to London, there is always something new to see, do or experience. The city is steeped in rich cultural history, but is also paired with a modernity and ease of getting around (e.g., tap-to-pay is ubiquitous) that few cities have achieved. Despite being a massive metropolis, it’s incredibly walkable and still maintains a human scale with the historic architecture. London has broken free of its past reputation for bad food and has become a wildly diverse and creative food scene. There’s something for everyone in London, and there’s never a bad time to go.
Complete Three Day London Itinerary
No matter how many times you’ve been to London, there is always something new to see, do or experience. The city is steeped in rich cultural history, but is also paired with a modernity and ease of getting around (e.g., tap-to-pay is ubiquitous) that few cities have achieved. Despite being a massive metropolis, it’s incredibly walkable and still maintains a human scale with the historic architecture. London has broken free of its past reputation for bad food and has become a wildly diverse and creative food scene. There’s something for everyone in London, and there’s never a bad time to go.
Planning a Destination Wedding on Cape Cod
Cape Cod is a summertime hot spot for locals and tourists alike, but it’s also a booming wedding destination for couples from all over the world. Known for its historic cottages and picturesque shoreline, a destination wedding on the Cape provides endless options for fun activities for your wedding weekend.
Planning a Destination Wedding on Cape Cod
Cape Cod is a summertime hot spot for locals and tourists alike, but it’s also a booming wedding destination for couples from all over the world. Known for its historic cottages and picturesque shoreline, a destination wedding on the Cape provides endless options for fun activities for your wedding weekend.
Summer in Boston
Boston is one of the most dynamic and exciting cities to visit in summer. Steeped in history and culture, Boston is walkable and tourist friendly. From world-class museums and sports teams to sunset cruises on Boston Harbor, there is so much to do in Boston in the summer, you might not even make it out for day trips to Cape Cod, Rhode Island, Vermont, New Hampshire or Maine.
Summer in Boston
Boston is one of the most dynamic and exciting cities to visit in summer. Steeped in history and culture, Boston is walkable and tourist friendly. From world-class museums and sports teams to sunset cruises on Boston Harbor, there is so much to do in Boston in the summer, you might not even make it out for day trips to Cape Cod, Rhode Island, Vermont, New Hampshire or Maine.
Complete Three Day London Itinerary
No matter how many times you’ve been to London, there is always something new to see, do or experience. The city is steeped in rich cultural history, but is also paired with a modernity and ease of getting around (e.g., tap-to-pay is ubiquitous) that few cities have achieved. Despite being a massive metropolis, it’s incredibly walkable and still maintains a human scale with the historic architecture. London has broken free of its past reputation for bad food and has become a wildly diverse and creative food scene. There’s something for everyone in London, and there’s never a bad time to go.
Complete Three Day London Itinerary
No matter how many times you’ve been to London, there is always something new to see, do or experience. The city is steeped in rich cultural history, but is also paired with a modernity and ease of getting around (e.g., tap-to-pay is ubiquitous) that few cities have achieved. Despite being a massive metropolis, it’s incredibly walkable and still maintains a human scale with the historic architecture. London has broken free of its past reputation for bad food and has become a wildly diverse and creative food scene. There’s something for everyone in London, and there’s never a bad time to go.
My travel photos
