How long have you been planning that trip of a lifetime?

Our resident travel expert, Jill Benedict, is back with us for a lively deep dive into the unpredictable world of family travel. From international cruises and unexpected illnesses to the logistics of planning multi-city adventures, Jill and I swap personal stories, travel mishaps, and insider tips you won't want to miss.

We dig into why cruises can simplify travel logistics, the value of private guides, and even compare dining across cruise lines. Jill also shares why booking excursions through the cruise company often pays off.

Our conversation goes deeper into the choices families face: balancing kids' sports schedules versus family vacations. From my daughter's swim meet to Jill's client balancing baseball with a Hawaii trip, we explore how to prioritize memories over moments that may not matter as much years from now

If you're on the fence about that "big" family trip, remember: you'll never regret time spent together, but you might regret the experiences you missed.

Please enjoy my conversation with Jill Benedict.

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Resources Featured in This Episode:

Wishes & Wonders Travel Agency

The Ultimate Guide to Stress-Free Family Vacation Planning

How to Master and Save Money on Family Vacations