The story behind Vacationeeze
Vacationeeze was created many years ago by Jack and Sharon Benoff with one sole purpose in mind: helping you “eeze” into your next adventure.
We’re client-centric and travel-obsessed with the goal of sharing our passion for travel with you as we partner together to plan your trip.
Over the past 15+ years, we’ve grown our family-owned business into one of the top award-winning independent travel agencies.
Even as we’ve grown, we kept the same ethos to ensure we pair our unrivaled travel knowledge with the niche travel experiences that matter most to our clients.
Over the years, our passion for wine and food has brought us to countless destinations, from Sonoma to Spain, from Portugal to Australia.
We love sharing our knowledge, experience, and joy with our clients to bring them authentic wine experiences.
Jack and Sharon’s son, Jared, now manages Vacationeeze full time so that Jack and Sharon can spend more time doing what they love…traveling and enjoying!
Our Travel Code of Ethics
At Vacationeeze, we believe the way you travel and the choices you make along the way are just as important as where you go.
At Vacationeeze, we believe that wine travel should be immersive, responsible, and enriching. Our small-group experiences are designed with care, ensuring a meaningful connection to the places we visit and the people who make them special.
- Authenticity Over Mass Tourism – We seek out under-the-radar vineyards, family-run wineries, and intimate experiences that capture the true essence of a region. When visiting popular destinations, we aim for off-peak times to support sustainable tourism.
- Respect for the Land & Its People – Every glass of wine tells a story of the land, the climate, and the people who nurture it. We travel with deep respect for the environment and local traditions, ensuring our experiences contribute positively to the communities we visit.
- Supporting Small Producers & Artisans – We prioritize partnerships with boutique wineries, local chefs, and artisans, ensuring that our visits benefit independent businesses rather than large corporations.
- Cultural Immersion Through Food & Wine – Wine is more than a drink—it’s a reflection of culture, history, and tradition. We take the time to truly experience each region through curated tastings, vineyard walks, and meals shared with winemakers.
- Small Groups, Big Connections – We believe the best travel experiences happen in intimate settings, where guests can form genuine connections with one another and with the locals who welcome us into their world.
- Sustainability & Stewardship – We minimize our footprint by supporting eco-conscious wineries, reducing waste during our tours, and making responsible travel choices, including offsetting carbon emissions where possible.
- Staying in Unique, Locally Owned Lodging – We avoid large, impersonal hotels and instead choose charming, boutique accommodations that reflect the character of the region, from countryside estates to historic inns.
- Keeping an Open Mind & Heart – Every destination has something to teach us. We embrace the unknown, try new flavors, and listen to the stories of the people we meet along the way.
- Travel as a Privilege – We recognize that the ability to explore the world through wine and culture is a gift, and we travel with gratitude, always striving to leave a place better than we found it.
At Vacationeeze, we don’t just visit wine country—we experience it with intention. Cheers to traveling responsibly, authentically, and deliciously!
Meet Our CEO
Who is Jared Benoff?
For Jared, travel isn’t just a job—it’s in his DNA. Growing up in a travel-loving family meant skipping school to for business meetings in new destinations with his dad (Vacationeeze’s founder) and celebrating his third birthday in Jamaica. These early experiences sparked a lifelong passion for discovering the world.
Before taking the reins at Vacationeeze, Jared built a career in government service and later in the private sector at a leading technology company. But his love for travel never faded.
Over time, he became more involved in the family business, eventually acquiring Vacationeeze when his parents retired.
Today, he blends his expertise with his deep appreciation for food, wine, and meaningful experiences to create unforgettable journeys for his clients.
Jared now calls Connecticut home, where he lives with his wife and son. Whether he’s uncovering hidden vineyards or curating immersive small-group tours, he’s passionate about helping others explore the world in a way that feels personal, seamless, and unforgettable.
Current favorite destination: Tokyo, Japan
Current favorite vineyard: Madson Wines, Santa Cruz, CA