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A family that's been obsessed with travel for 35 years
It started when Jack and Sharon were 15
They met as teenagers and have been traveling together ever since. What started as a shared passion became a career.
In the early 2000s,Jack built and sold one of the first online destination wedding and honeymoon booking platforms to The Knot, where he went on to become president of a division. He's been shaping the way couples plan destination weddings for over two decades. But they never wanted to run a platform. They wanted to run a travel agency, one where the advice comes from someone who has actually been there. Today, Jack and Sharon travel nearly three weeks every month, visiting resorts, meeting wedding coordinators, and checking on venues in person. When they recommend a resort, they've stood in the ceremony space themselves.
Their son Jared joined the team and carries the same ethos forward. This is a family business in the truest sense, and when you work with them, you can feel the difference.
What makes us genuinely different
Not virtually. Not via a brochure. Jack and Sharon are on the road nearly three weeks a month, visiting destinations, inspecting ceremony venues, and building relationships with resort wedding coordinators. When they say a venue is right for you, they've stood in it themselves.
We're compensated directly by the resorts we book, which means you get a dedicated team managing your room block, coordinating your guests, and handling every detail from contract to checkout, at no cost to you. There's no catch. That's just how the industry works when you're with an agency resort partners trust.
Most couples don't realise how much of a destination wedding is managing 50 other people's travel logistics. We take that entirely off your plate — handling individual guest bookings, room block management, late-night questions, and last-minute changes — so you can focus on the parts that actually matter.
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Jack & Sharon Benoff
Jack and Sharon built their careers around a simple belief:the best travel advice comes from someone who has actually been there. Before recommending a resort, they visit it. Before suggesting a ceremony venue, they've stood in it. Before telling you which wedding coordinator to trust, they've worked with them in person.
Jack's background spans the full evolution of destination travel — from founding one of the internet's first destination wedding platforms (later acquired by The Knot, where he became a division president) to building Vacationeeze into an award-winning family agency with recognition from The Knot, WeddingWire, and major resort partners across Mexico and the Caribbean.
Sharon brings warmth and obsessive attention to detail that every couple who's worked with her notices immediately. She's the person who calls you from her own son's wedding to make sure your resort issue is being handled.
Jared Benoff
Jared didn't just grow up around this business — he grew up inside it. Family dinners were resort reviews. School holidays were site visits. He watched Jack and Sharon build something that worked because it was built on relationships and real knowledge, not algorithms and affiliate links.
When he took over, he didn't change that. He rebuilt the infrastructure around it. Better tools for couples to research resorts before they call. A planning process that works the way people actually think today. Content that treats you like an intelligent adult who deserves real information, not a sales funnel.
The advice still comes from someone who has actually been there. The resort relationships are still 35 years deep. What's different is everything around it — the reach, the resources, and the platform that makes all of that easier to access. That's Vacationeeze 2.0.
The experts behind your trip
Awards & certifications
What our clients are saying
We were looking at destination weddings in Cancun and saw a lot of great reviews about Vacationeeze so we scheduled an initial call, which went really great with Jared. Highly recommend Vacationeeze for destination weddings!
5/5We had 45 guests fly in from across the country and every single one of them said it was the best wedding they had ever attended. The team at Vacationeeze handled every detail from room blocks to transfers to the ceremony itself. I did not stress once during the entire planning process. Cannot recommend them enough.
5/5Although I am an avid traveler and feel comfortable navigating the travel world, Penny took away the need for me to do any thinking! She communicated promptly, sent confirmations timely, and even answered all of my silly questions. We had a great time at the wedding and had absolutely no issues with accommodations or transfers to and from the airport. If you want a smooth vacation, she's your gal!
5/5
We quickly decided we didn't want to do a local wedding, so we started looking up YouTube videos of destination weddings. We found Jack and fell in love with him. We loved how he was a no nonsense type of guy that wasn't trying to sell anyone on anything, he was just stating facts and his knowledge. We quickly decided that we wanted Jack to be the one to help us figure out a destination wedding for us.
5/5Zandra Valenti has been incredible to work with and has made the entire process easy and smooth. Highly recommend using her for future vacation planning. Quick responses, helps you through the process and answers any questions promptly along the way. Can't recommend enough!
5/5
I cannot recommend Jared highly enough. The trip surpassed my expectations, and I am grateful for the meticulous planning and personalized attention provided by Jared. If you're looking for a travel planner who combines expertise with a genuine passion for creating memorable experiences, look no further! Thank you, Jared, for making my trip truly unforgettable. I look forward to planning my next adventure with your expertise!
5/5Everyone told us sunsets in Negril were special but nothing prepared us for what the ceremony actually looked like. The photos are incredible. Our advisor at Vacationeeze specifically recommended a 5pm ceremony timing to catch the golden hour over the water and it made all the difference. Every guest was speechless.
5/5Vacationeeze is amazing. From the moment we contacted them, they provided exceptional service and expertise that made our destination wedding truly unforgettable. Jeff recommended and helped us pick the perfect resort for our special day. His attention to our vision and budget ensured we chose a resort that would fit our wedding expectations.
5/5Jack Benoff did a great job negotiating our contract with the Dreams Playa Mujeres Resort and explaining all the pros and cons of selecting the rooms to offer our group! Likewise, our concierge Leslie was exceptional at coordinating the booking of rooms for our guests, arranging all the travel to and from the resort, and handling the last-minute changes to our booking. Everyone at Vacationeeze was highly responsive and a pleasure to deal with!
5/5Our advisor suggested spending half the week eating our way through Grand Case on the French side and it was the best suggestion anyone made during our entire planning process. The wedding at Sonesta Ocean Point was beautiful and then we had this whole second chapter of the trip that felt completely different. Vacationeeze understood exactly the kind of experience we were looking for.
5/5
What a gorgeous resort! From the swings at the bar to the numerous pools… Many thanks to Zandra and Vacationeeze for planning such a dream vacation to El Dorado Maroma in Playa del Carmen last November! It was a beautiful location and the organized events were perfect! We had a delicious dinner on the beach that was beautifully decorated with flowers and lights… just magical! Thank you Zandra, for picking such an amazing resort - we loved the Mexican night, the tequila tasting, and the mariachis! We will be returning for more advice from you in the future!!
5/5We chose Playa Mujeres on Jack's recommendation and it was the best decision of our entire wedding planning process. The beach was pristine, the resort team was exceptional, and our guests felt like they had the whole place to themselves. Nothing like the crowded hotel zone we had been looking at before we called Vacationeeze.
5/5We had 60 guests come to Punta Cana and the logistics of that alone felt overwhelming before we found Vacationeeze. Our advisor managed the entire room block, coordinated all the transfers, and worked directly with the resort wedding team so we never had to play middleman. The ceremony on the beach at Secrets Cap Cana was perfect.
5/5
4.9/5Where to next?
We are here to help with any wedding and travel plans.
