Episode Summary
In this episode of The Cool Grandpa Podcast, I sit down with Stefanie Shackelford, founder of Odyssey Travel, to explore how travel has evolved—and why experienced travel advisors matter more than ever, especially for grandparents planning meaningful trips with their grandchildren.
With over 40 years in the travel industry, Stefanie shares how travel planning has shifted from handwritten tickets and phone-book-sized fare manuals to today’s digital-first world—while explaining what technology still can’t replace: human insight, experience, and relationships.
Together, we dive into:
- The hidden value of working with a professional travel advisor
- How multi-generational and “skip-gen” travel is reshaping family experiences
- Why grandparents are uniquely positioned to create unforgettable travel memories
- How travel agents personalize trips based on family dynamics, budgets, and kids’ ages
- The growing appeal of national parks, cruises, trains, and cultural experiences
- What to look for when choosing a travel agency—and red flags to avoid
- Why travel insurance matters more today than ever
This conversation is a must-listen for grandparents who want to travel smarter, reduce stress, and build deeper bonds with their grandchildren through shared experiences.
If you’re a grandparent dreaming about meaningful trips with your grandkids—but don’t want the stress of planning—this episode is for you.
👉 Listen now and discover how experienced travel advisors help grandparents create unforgettable, age-appropriate adventures that build lifelong memories.
Links
Click on this link to visit Odessy Travel: https://www.team-odyssey.com/
Here is Stefanie’s email address: sjs@team-odyssey.com
You can use this phone number to reach out to Stefanie and Odessy Travel: 707-343-7112
You can watch this fun conversation on YouTube by using this link: https://youtu.be/wfWvWW3Dg1o
I would appreciate it if you could support the show. You can support the show through “Buy me a Coffee” and donate a few dollars by clicking HERE. (https://buymeacoffee.com/coolgrandpa)
Here is a link to my webstore: https://cool-grandpa.com/shop/
More Than Grand 
Grandfathers have a unique and meaningful role to play in grandchildren’s development, yet they often find themselves behind the scenes, on the sidelines, or less engaged than they’d like to be. This masterclass delivers a playbook for helping grandfathers level up their influence and impact. Listeners to The Cool Grandpa Podcast can receive 40% off this course by using Cool40 at checkout.
Founded in 2011 by Aaron Larsen as a way to honor his grandparents, GrandparentsAcademy.com is the world’s first and only online academy dedicated to helping grandparents grow meaningful relationships and rich legacies with their loved ones.
