True Travel Talk

Can you conquer Porto’s hills, markets, and port houses before the kids (and the clock) call it quits?

For the final stop of their Portugal adventure, Jill, her husband Paul, and her travel crew head north with ambitious plans and varying levels of enthusiasm. After a forest hike, a controversial suckling pig lunch, and a family-history detour, they take on Porto one hill at a time. Fueling the adults with port, the boys with...

34. Sometimes the best part of getting somewhere is everything you refuse to rush past.

In Part 2, Jill’s multigenerational crew trades the Algarve for Lisbon, turning the road through Évora and a day trip to Sintra into two packed days of history, food, and family detours. It’s also a reminder that family travel works best when no one is expected to experience a destination in exactly the same way.

In This Episode

33. Travel rarely waits for life to feel simple.

True Travel Talk returns for Season 4 with a multigenerational spring break adventure through Portugal. Jill, her husband Paul, mom Sheri, and sons Graeme and Luke begin in the Algarve, proving that changing plans, missed reservations, and one spectacularly soggy boat launch don’t have to derail a great trip.

From a coastal drive filled with beaches, cork trees, and Portugues...

32. Can you fly halfway around the world, explore Taipei with a child and two grandmothers, and still call it a long weekend? 

For the Season 3 finale, Jill takes advantage of a Delta fare sale and turns her son Graeme’s Christmas present from his grandmothers, Donna and Sheri, into a fast-moving, food-filled family adventure in Taiwan. With only a few days on the ground, the group balances carefully planned experiences ...

31. Is Bhutan’s most famous view worth a six-hour climb?

In the final episode of True Travel Talk’s three-part journey through Bhutan, Jill, Jen, and Emily arrive in Paro for a finale filled with cultural immersion, unexpected friendships, and the trip’s most anticipated challenge: hiking to the cliffside Tiger’s Nest monastery.

With their Bhutanese guide-and-driver team, Sonam and Pee Dee, they move beyond ...

30. Can a trip be deeply spiritual, completely ridiculous, and genuinely transformative – all at once?

In Part 2 of True Travel Talk’s three-part journey through Bhutan, Jill and her travel team move from the mountains surrounding Thimphu into Punakha, the country’s lush former capital. Known for its terraced rice fields, warmer climate and majestic riverside fortress, Punakha offers a different side of the Land o...

29. Where is Bhutan – and why does traveling there feel unlike anywhere else? 

Tucked between India and China in the Himalayas, Bhutan is a small Buddhist kingdom known for towering mountains, deep traditions, and an unusually intentional approach to tourism.

This episode kicks off a three-part True Travel Talk series from Bhutan. First stop: Thimphu, the country’s capital. Jill travels with her sister-in-law Emily...

28. What can you really experience in Bangkok when you arrive late, leave before sunrise the following day, and discover that half the places on your list are closed?

More than you might think…provided you are willing to abandon the perfect itinerary.

After flight disruptions shortened their visit, Jill arrives in Bangkok for the first time with Jen and Emily - both returning visitors. Rather than force their original plan, ...

27. What happens when your first trip overseas is a last-minute journey to East Africa?

In Part 2 of Jill’s conversation with Michelle, True Travel Talk continues the story of Michelle’s very first abroad adventure - a trip she said yes to before she felt fully ready. After the travel chaos of getting to Tanzania, this episode moves into the moments that made the leap worth it: beautiful stays, shared meals, Maasai hosp...

26. What if your first trip overseas was not something you planned for years, but a last-minute leap to East Africa?

In this “Unpacked” episode of True Travel Talk, Jill sits down with friend Michelle to talk about saying yes before you feel ready - and what happens when the trip tests you before you even arrive. Michelle’s first international trip was a last-minute journey to Uganda and Tanzania, filled with the ...

25. This episode takes us to Philadelphia for a food-focused conversation with Jill’s friend and colleague, Jen Floyd, about experiencing a city through what you eat, where you wander, and the stories you collect.

Philadelphia is known for its iconic traditions, but this conversation goes beyond the obvious. Jill and Jen talk about the joy of building a trip around local flavor - from classic Philly bites to neighborhood stop...

24. This episode brings Jill’s Germany story full circle. After beginning the trip in Garmisch-Partenkirchen - the place that inspired the very first episode of True Travel Talk - the family splits off in different directions, with Jill’s travel team heading toward one of Germany’s most storybook regions: the Black Forest.

Along the way, they stop in Ulm, revisit favorite sights like the Ulm Münster and Rathaus, a...

23. In the final installment of their South Africa family adventure, Jill and her son Luke discover why the vibrant coastal town of Cape Town is considered one of the world’s most beautiful destinations.

From African penguins at Boulders Beach to sweeping views atop Table Mountain, Cape Town showcases the perfect blend of culture, adventure, and natural beauty. Along the way, the family discovers colorful neighborhoods, drama...

22. In part two of our South Africa family adventure, Jill and her family trade safari vehicles for vineyard views as they explore the spectacular wine regions of Franschhoek. 

Often called the food and wine capital of South Africa, Franschhoek combines centuries-old vineyards, dramatic mountain scenery, world-class restaurants, and charming small town streets. Over several days, they experienced everything from olive oil tast...

21. Join Jill and her family as they journey from Cape Town to Gondwana Game Reserve for an unforgettable stay at this private retreat, featuring game drives, a personal guide, and sweeping mountain views.

From early morning safaris to evenings around the braai, this episode captures the excitement, beauty, and quiet family moments that made the experience memorable.

Along the way, Jill, husband Paul, and son Graeme talk about thei...

20. Join Jill and her friend Whitney as they check off a true bucket-list moment from their girls trip: heading into and out of Machu Picchu in style aboard the iconic Belmond Hiram Bingham Train.

Named after the explorer, Hiram Bingham, this isn't just transportation, it's an experience in itself. The journey blends old-world glamour with Peruvian culture; polished wood interiors, live music, elevated dining, and cocktails that ne...

19.2 Join Jill and her crew, including friends Amy and Kelly, as they continue their journey through Peru’s Sacred Valley - where the experience goes deeper than the views and into the heart of the Andean culture.

In Part 2 of the Sacred Valley, this girls trip shifts from adventure to connection - exploring what it means to truly experience a place, not just see it. From wandering through the last living Inca village to shar...

19. Join Jill and her crew, including friends Amy and Kelly, as they head to Peru’s Sacred Valley - where the views are unreal, the culture runs deep, and yes…there are a lot of alpacas. 

As the fourth stop in our Peru series (after Cusco, Machu Picchu, and Lima), this episode proves the Sacred Valley isn’t just a pass-through - it’s the moment you exhale, settle in, and really feel the magic of Peru.

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18. Join Jill and her son Graeme as they share their spontaneous family trip to Miami, exploring beaches, iconic landmarks, and local culture. From watching manatees right outside their hotel window to walking to a Miami Heat game, the trip blended big moments with simple joys. Traveling with kids, navigating unexpected changes, and making unforgettable memories showed us that sometimes the best trips are the ones you didn’t ...