The People Behind Wander Well

Meet Your Travel Advisors

Your guides to the world. Two advisors who turned a passion for travel into a purpose: helping you experience it better.

Your Guides to the World

We're not just booking trips.
We're building memories.

Jennifer and Deann bring combined decades of travel experience, an extensive network of trusted suppliers, and a genuine love for the art of a perfectly crafted journey. When you work with Wander Well, you're not a booking number — you're a traveler with a story we want to help tell.

Jennifer Chernay at the Great Wall of China
Jen Travel Advisor

Jennifer Chernay

Co-Founder & Travel Advisor · Wander Well Travel

Jennifer's love of travel started long before Wander Well did — and it never stopped. With a talent for finding the hidden gems in every destination and a gift for making the complex feel effortless, Jen specializes in crafting journeys that feel tailored, not templated.

Whether she's planning a dream honeymoon in Bali, orchestrating a multi-generational family reunion in Italy, or coordinating a group of friends on a river cruise through Europe, Jen brings the same meticulous attention and personal warmth to every booking.

She's passionate about matching each traveler with experiences that genuinely reflect who they are — because she believes the best trip isn't the most expensive one, it's the one that feels most like you.

Luxury Travel Honeymoons River Cruises Europe Family Travel All-Inclusive
Deann Rios in Santorini, Greece
Deann Travel Advisor

Deann Rios

Co-Founder & Travel Advisor · Wander Well Travel

Deann is the kind of travel advisor who gets genuinely excited about your trip — sometimes even before you do. Her energy is contagious, her network is deep, and her dedication to making every journey feel special goes far beyond the booking confirmation.

Deann has a particular passion for group travel, bringing friends, families, and communities together around shared adventures. From the logistics of coordinating a dozen people to the small personal touches that make a group trip feel like a gift — she lives for it.

When she's not planning someone's next great adventure, you'll likely find her planning her own. She travels constantly, stays up to date on destinations and trends, and returns home with fresh insights that benefit every client she works with.

Group Travel Adventure Travel Ocean Cruises Celebrations Multi-Gen Families Culinary Travel
Kahala Travel

The Network Behind the Experience

Wander Well Travel is proudly affiliated with Kahala Travel — an established travel company with deep supplier relationships, preferred status with leading cruise lines, hotel groups, and tour operators, and a commitment to excellence that extends to every advisor in their network.

This affiliation means Wander Well clients benefit from negotiated rates, preferred perks, and the kind of supplier accountability that only comes from being part of a trusted travel network — without losing the personal, boutique-agency feel that makes Wander Well unique.

Learn About Kahala Travel ↗

Our Values as Your Travel Advisors

These aren't just words on a website — they're the lens through which we plan every trip and maintain every client relationship.

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Honesty

We tell you what's worth the price and what isn't — even when it means recommending a less expensive option.

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Curiosity

We stay curious about destinations, suppliers, and new travel experiences so our recommendations stay fresh and informed.

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Partnership

We see every client relationship as an ongoing partnership — not a one-time transaction. We grow better together.

Excellence

From the first inquiry to the final debrief, we hold ourselves to a standard of care that reflects the trust you place in us.

Start the Conversation

Let's Plan Your Next Adventure

Ready to travel smarter, not harder? Reach out to Jen or Deann and let's talk about where in the world you want to go next.

Let's Start Planning! Say Hello

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