Episode 196: Smart Money Moves for Family Vacations with Skyler Fleming

For most families, the biggest obstacle to taking that dream trip isn’t time—it’s money. The good news? With a little planning and some smart financial strategies, you can make vacations happen without draining your savings or piling on debt.

In this episode, Rob talks with Skyler Fleming, Certified Financial Planner and host of the Money Talks podcast. Skyler shares practical tips to help families budget, save, and plan so travel dreams can become travel memories. From avoiding credit card traps to involving kids in the budgeting process, this conversation is packed with actionable advice for making travel financially doable—and fun.

What You’ll Learn in This Episode:

• Why “splurging comfortably” is possible with the right budget
• The first steps families should take when creating a vacation budget
• Common costs families forget to plan for (and how to avoid surprise expenses)
• How far in advance you should start saving for a big trip
• Simple savings strategies that won’t eat into everyday essentials
• The truth about credit card rewards—and how to use them wisely
• Fun ways to involve kids in vacation budgeting and decision-making
• Why planning ahead reduces pressure and makes vacations more enjoyable

About Our Guest

Skyler Fleming is a Certified Financial Planner and the host of the Money Talks podcast, where he helps people build strong money habits. His practical, down-to-earth approach helps families think differently about budgeting and saving so they can enjoy life—and travel—without financial stress. Learn more at MoneyTalk.show.

Resources & Links

• Visit Skyler’s website: MoneyTalk.show
• Listen to the Money Talks podcast on your favorite platform
• Follow The Family Vacationer on Instagram and Substack

Don’t Miss

Rob’s upcoming book, The Family Vacationer: A Parent’s Guide to Meaningful Travel, is on the way! Filled with stories and tips to help you make your trips more meaningful, it’s coming soon—stay tuned for details.