Jennifer Gilley

• Founder & Lead Travel Advisor, 

Journey Through Generations Travel

Helping families reconnect through unforgettable, stress-free travel experiences

For over eight years, I’ve helped families just like yours plan seamless, meaningful vacations around the world—from multigenerational cruises and Caribbean getaways to once-in-a-lifetime European adventures.

But my journey didn’t start with a travel agency—it started with my own family.

As a mom of two now-grown boys, I’ve spent decades planning travel that brought us closer together. We’ve explored the wilds of Alaska, relaxed on the beaches of the Caribbean, and navigated international adventures across Mexico, Canada, and beyond. I understand firsthand the power of a well-planned trip—and the stress it can cause without expert support.

That’s why I created Journey Through Generations Travel: to give busy parents, loving grandparents, and extended families a better way to travel—one that prioritizes connection, celebration, and ease.

🔹 Expertise in Multi-Generational Travel
I specialize in planning trips that meet the needs of multiple age groups—whether it’s a cruise with your adult kids and grandkids, or a milestone celebration across generations.

🔹 Full-Service Planning, Start to Finish
From flights and accommodations to excursions, travel insurance, and hidden gems, I handle every detail so you can focus on making memories—not managing logistics.

🔹 Trusted Industry Knowledge
I partner with leading cruise lines, luxury resorts, and travel suppliers to bring you exclusive perks, upgrades, and customized experiences that online platforms simply can’t offer.

🔹 A Personal Touch
No two families are the same—so no two trips should be either. Every itinerary I design is tailored to your travel style, your interests, and the unique dynamics of your group.

• 8+ years as a professional travel advisor
   
• Founder of Journey Through Generations Travel
   
• Specialization in family travel: Caribbean All-inclusive Resorts, Ocean Cruises: Disney, Royal Caribbean, Norwegian, Princess and Virgin Voyages. Theme Park Travel. Customized European Itineraries, Hawaii and Alaska.
   
• Recognized for proactive client care, thoughtful planning, and delivering exceptional travel experiences—even in unexpected circumstances.

• ASTA Member

• Brand Certifications: Disney College of Knowledge, Certified Universal Specialist, Royal Caribbean Cruise Line, Princess Cruise Line, Apple Leisure Group Pro Agent, Signature Travel Network Travel Expert.
   

To help families travel better, together—through expertly crafted vacations that inspire connection, celebrate life’s milestones, and create stories you’ll share for generations.

If you're looking for a travel advisor who truly understands what families need—because she’s lived it—I’d love to be part of your journey.

📅 Let’s plan your next family adventure together