Ep. 213 – Jill Benedict – Family Travel: Adventures and Challenges in Building Lasting Memories
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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ADDITIONAL RESOURCES YOU MAY LIKE
1 Big Idea to Think About
While juggling family activities, busy schedules, and travel logistics can be overwhelming, intentionally planning memorable trips—especially early—helps create lasting experiences that often matter more in the long run than day-to-day commitments or youth sports tournaments. Prioritizing these shared moments not only strengthens family bonds but also builds a legacy of meaningful memories.
1 Way You Can Apply This
To simplify and enrich your travel experiences, consider booking private guided tours—while they may be more expensive, having a local expert tailor your itinerary and navigate logistics can make each day memorable, maximize your limited vacation time, and ensure you fully enjoy once-in-a-lifetime destinations without unnecessary stress or missed opportunities.
1 Question to Ask
What memories and experiences do I want to prioritize with my family, and how can I make the most of the limited time I have with them before major life transitions occur?
Key Moments From the Show
00:00 Jill recounts getting sick on multiple cruises, urgent care visits, and the unpredictability of travel illnesses.
01:52 Tom shares advice for cruise travelers: always pack a pharmacy, as getting medicine abroad can be challenging.
03:53 Highlights meeting new friends on cruises, and the benefit of being prepared with medicine on trips.
05:00 Jill describes a Mediterranean cruise to Rome, Santorini, Mykonos, Ephesus, and Naples—trip highlights and magical dinner moments.
07:16 The value of private guides in Rome—how personalized tours made the experience unforgettable and efficient.
08:57 Tom discusses networking with trusted local guides in Italy and the importance of well-organized transfers and tours for smooth travel.
12:06 Comparing cruises to land-based travel—cruises remove much of the logistical stress, allow for more destinations, and provide a relaxing “home base.”
14:18 Exploring Naples-style excursions: Pompeii, Amalfi Coast, Capri, and discovering hidden gems like Sorrento.
16:46 Maximizing pre- and post-cruise time—front-loading major sightseeing allows for a more relaxing end to the trip.
17:35 Staggering excursions on longer cruises to avoid travel fatigue and taking advantage of cruise line flexibility with excursions.
19:21 Importance of booking excursions through the cruise line: the ship will wait if you're delayed, providing vital peace of mind.
20:56 Dining package comparison—Royal Caribbean versus Disney Cruise Line food, and the impact of local sourcing in Europe.
23:01 Tom suggests Celebrity Cruises for best food—more adult-focused with renowned chefs and higher-quality offerings.
25:15 Planning family travel amid kids’ activities—navigating sports, school schedules, and the benefit of booking early for price and selection.
27:19 Real-life dilemma: moving a Hawaii trip due to a child’s baseball tournament, weighing once-in-a-lifetime vacations versus youth sports.
31:02 Jill and Tom discuss priorities—balancing family experiences, sports, finances, and the importance of memory-making vacations.
38:53 The perspective that kids won’t remember how much a trip cost, but will remember the memories made.
41:04 Benefits of working with a travel advisor for unexpected issues and cancellations—insider access to customer service and policy exceptions.
42:09 Jill’s “calendar of memorable moments”—visualizing summers left with kids, and the emotional impact of seeing limited time together.
44:31 The significance of fostering family bonds; hoping children return as adults to create new memories.
45:29 Trends in multigenerational travel—adult children now treating their parents to elaborate family vacations.
48:11 Jill shares where to find her agency, Wishes and Wonders Travel, and the challenge of juggling business with social media presence.
51:02 Closing advice: book family trips early—school and sports schedules fill up fast, popular destinations sell out years in advance.
Resources Featured in This Episode:
Wishes & Wonders Travel Agency