How to Travel Like an Insider: Jeremy Mendelsohn’s Guide to Authentic Experiences

Jeremy Mendelsohn is a seasoned professional in the travel industry with a passion for creating memorable experiences for students. As the Director of Strategic Accounts at All Roads Travel, he has overseen travel programs that have allowed over 500,000 students to explore destinations across the globe. Jeremy’s work centers on making travel accessible and impactful for young people, providing them with opportunities to learn and grow outside the classroom.

Originally from Calabasas, California, Jeremy grew up active in sports and community life. He attended San Diego State University, where he earned a degree in Integrated Marketing Communications and was heavily involved in campus organizations. While studying abroad in China, he gained hands-on experience in international business and travel, sparking his interest in the industry.

At age 24, Jeremy founded TravelZeeky, a company focused on group travel for students and corporate clients. Over five years, he led the company to impressive growth, organizing over 1,000 events and generating more than $40 million in revenue. In 2018, TravelZeeky was acquired by a London-based events firm, a milestone that opened new doors for Jeremy’s career.

Today, Jeremy brings his experience and dedication to All Roads Travel, where he develops partnerships, plans large-scale trips, and ensures each experience offers cultural and educational value. He’s known for his collaborative approach and adaptability, particularly during challenges like the COVID-19 pandemic, when he helped shift the company’s focus to virtual and at-home travel experiences.

Outside of work, Jeremy is active in his community, regularly participating in charity events and staying involved with his local synagogue. He’s visited 41 countries so far and aims to experience every continent, continuing to feed his love for exploration and cultural connection.

What do you usually look for in a holiday destination? 
I love a destination that offers a mix of relaxation and adventure. For me, it’s about having options—I want a place where I can relax by the water one day and explore something unique or cultural the next. A great holiday destination has a little of everything: beautiful scenery, interesting local culture, and, of course, good food!

Do you prefer big cities or off-the-beaten-path spots? 
Both have their appeal! Big cities can be incredible—there’s always something happening, and I enjoy the energy and diversity. But I’m also drawn to quieter, less-traveled places. I love getting to know a destination that feels untouched, where you can take your time exploring without the crowds.

What’s one destination you would visit over and over? 
Japan, hands down. It has everything—a unique mix of ancient culture and modern innovation, beautiful landscapes, and some of the best food I’ve ever tasted. Each region is so different, and I feel like I discover something new every time I go.

Do you have a favorite beach or nature destination? 
I’d say the Amalfi Coast in Italy. The scenery is unbelievable, and there’s nothing like spending a day exploring the cliffs and small towns along the coast. Plus, there’s something about the Mediterranean lifestyle that just makes you slow down and enjoy the moment.

Any underrated destinations you’d recommend? 
Portugal is incredible but often overlooked. It has beautiful coastlines, amazing food, and the people are so welcoming. Lisbon and Porto are fantastic cities to explore, and there are countless small towns and beaches that give you a feel for the country’s character.

What’s your ideal travel day like? 
I’d start with a big breakfast—food is definitely a highlight for me when I travel. Then, I’d spend part of the day exploring something cultural, like a historic site or local market, before finding a quiet place to relax. Ideally, I’d end with a great dinner and maybe a walk around the city or by the water. It’s all about balance!

Do you have a type of accommodation you prefer when traveling? 
I actually enjoy a mix! Sometimes a hotel with good amenities is exactly what I want, but other times I prefer a local guesthouse or even a homestay. It’s all about connecting with the place I’m visiting, and sometimes a smaller, locally run spot gives you more of that authentic feel.

How much do you plan your trips in advance? Are you a planner or do you go with the flow? 
I like to have a few things planned, especially the must-see spots or any unique experiences, but I leave a lot of room for spontaneity. Some of the best travel moments happen when you follow a suggestion from a local or stumble upon something by chance. So, I guess I’d say I’m a “hybrid” traveler—part planner, part explorer!

What’s one memorable experience you’ve had while traveling? 
One that stands out was when I was traveling in Thailand and got invited to a local festival by some people I met there. I had no idea what to expect, but it turned out to be an incredible experience. There was so much energy, and it felt amazing to be welcomed into something so personal to their culture. It reminded me how travel really brings people together.

How important is food to you when you choose a destination? 
Food is huge! I feel like you can learn so much about a place just through its food. I’m always on the lookout for local dishes and traditional restaurants, and I love trying things that aren’t typical back home. Food is one of the easiest ways to connect with people and their culture, and it’s always an adventure!

What’s one travel item you never leave home without? 
I never go anywhere without a good pair of walking shoes. I’m usually on my feet a lot when I travel—whether I’m exploring a city, hiking, or just wandering through markets. Comfortable shoes make all the difference!

What’s one travel lesson you’ve learned over the years? 
I’d say patience and flexibility are key. Travel doesn’t always go as planned, and that’s okay. Sometimes those unexpected changes lead to the best stories or experiences. I’ve learned to relax and go with the flow when things don’t go perfectly—it’s all part of the adventure.

Finally, if you could give one piece of travel advice, what would it be? 
Don’t just focus on seeing all the “top spots.” Slow down and get to know the local side of a place. Talk to people, visit the less-known areas, and give yourself time to just enjoy being there. The memories you’ll create that way are always the most meaningful.

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