15.1 Travel rarely goes the way you want it to - especially with kids, grandparents, and a full itinerary.

In this episode of True Travel Talk, Jill and her husband, Paul, unpack years of real-life travel mishaps across the all-too-relatable theme: delays and disruptions.

Some moments were stressful. Some were funny in hindsight. A few were genuinely hard. But over time, they’ve learned something important: when you lean into what goes wrong instead of resisting it, those road bumps often become the stories that define the adventure.

From missed flights and wet passports to urgent care visits on vacation, this episode is a reminder that travel isn’t about perfection - it’s about flexibility, resilience, and recognizing the bright side along the way. Because sometimes the detour is the destination.

13. Sometimes the best way to experience Healdsburg is to slow down, wander, and follow your tastebuds. In this episode, Jill and colleague Jen sneak in a wine country getaway into a work trip - exploring downtown Healdsburg, the rolling Dry Creek Valley, and a few unexpected local gems along the way.

From a bucket-list dinner at three-Michelin-star SingleThread to honey tastings at La Ruche, olive oil flights at Trattore Farms, and spontaneous sips of bubbly Barbera at Portalupi Wine, this trip is Healdsburg at its best: luxurious yet approachable, full of flavor, and endlessly surprising.

Travel & Experience Highlights:

• SingleThread - Three-Michelin-star dining rooted in farm-driven excellence.
• Hotel Trio Healdsburg - A well-located Marriott property with shuttle service and breakfast included.
• Black Oak Coffee Roasters - Award-winning craft coffee with sustainability at its core.
• La Ruche - Honey tastings, mead flights, and global varietals.
• Portalupi Wine - Italian heritage wines with playful energy.
• Regiis Ova - Sustainably sourced caviar from Chef Thomas Keller’s trusted farms.
• Dry Creek General Store - Historic deli + picnic stop since 1881.
• Dutcher Crossing Winery - Estate wines and heartfelt hospitality.
• Trattore Farms - Estate olive oils and vinegar pressed on-site.
• Williamson Wines: Bill’s Cellar - Casual, community-driven wine experiences.
• Montage Healdsburg - Elevated resort dining with vineyard views.

For more stories with Winemaker Bill Williamson, check out Episode 9 of True Travel Talk, “France: Loire Valley - A Road Trip with a Winemaker.”

About Our Guest: Jen Floyd is a longtime friend and colleague, and is a curious explorer who turns every adventure - from wineries to honey tastings - into a story worth savoring.

About the Show: True Travel Talk takes you around the world with real stories, honest tips, and inspired itineraries — from family adventures to faraway escapes, always grounded in connection and curiosity.

Follow along on Instagram: @truetravelcrew & TikTok: @truetravelcrew

Executive Producer & Host: Jill Bohaboy Produced by: Collective Change Communications — Kelly Sakalas & Jeni Keeler

12.2 In Part Two, Jill and Deanna continue their conversation, reflecting on a festive trip through Germany’s Christmas Markets with lessons learned, favorite moments, and practical tips.

From Augsburg and Ulm to Würzburg and Frankfurt, this two-part conversation focuses on the feel of winter travel: navigating cold weather, moving at a multigenerational pace, and leaning into the magic (and mishaps) that come with traveling together.

Travel & Experience Highlights:

• Augsburg WeinNachtMart
• Ulm Christmas Market & Medieval Market (Neu-Ulm)
• Würzburg Christmas Market
• Frankfurt Christmas Markets & City Beach Market
• Feller Distillery (Black Forest)
• White sausage breakfast in Ulm
• Winter train travel through Germany

Hotels & Restaurants Mentioned:

• Hotel um Rathaus (Ulm)
• Dreikannen (Ulm)
• Posthorn (Ulm)
• Feller Distillery
• Wirsthaus zur Brezel (Ulm)
• AC Hotel Würzburg
• Pino Pizza (Würzburg)
• Bürgerspital Winery (Würzburg)
• Alte Mainmühle (Würzburg)
• Frankfurt Marriott Hotel

About Our Guest: Deanna Vogelsong is a longtime friend of Jill and a seasoned traveler who brings warmth, humor, and curiosity to every trip. Follow Deanna here:

• Insta: @kingbirdsings
• TikTok: @sweetTakes

About the Show: True Travel Talk takes you around the world with real stories, honest tips, and inspired itineraries — from family adventures to faraway escapes, always grounded in connection and curiosity.

Follow along on Instagram: @truetravelcrew & TikTok: @truetravelcrew

Executive Producer & Host: Jill Bohaboy Produced by: Collective Change Communications — Kelly Sakalas & Jeni Keeler

12.1 There’s something special about winter travel – especially when it’s shared across generations. In Part One of this two-part episode, Jill is joined by her longtime friend Deanna Vogelsong to reflect on a festive trip through Germany’s Christmas Markets with husbands, a “third grandmother,” and a 19-year-old son in tow.

From Augsburg and Ulm to Würzburg and Frankfurt, this conversation focuses on the feel of winter travel: navigating cold weather, moving at a multigenerational pace, and leaning into the magic (and mishaps) that come with traveling together. This episode is about presence, flexibility, and why imperfect trips often become the most meaningful. Part Two continues the journey with lessons learned, favorite moments, and practical tips.

Travel & Experience Highlights:

• Augsburg WeinNachtMart
• Ulm Christmas Market & Medieval Market (Neu-Ulm)
• Würzburg Christmas Market
• Frankfurt Christmas Markets & City Beach Market
• Feller Distillery (Black Forest)
• White sausage breakfast in Ulm
• Winter train travel through Germany

Hotels & Restaurants Mentioned:

• Hotel um Rathaus (Ulm)
• Dreikannen (Ulm)
• Posthorn (Ulm)
• Feller Distillery
• Wirsthaus zur Brezel (Ulm)
• AC Hotel Würzburg
• Pino Pizza (Würzburg)
• Bürgerspital Winery (Würzburg)
• Alte Mainmühle (Würzburg)
• Frankfurt Marriott Hotel

About Our Guest: Deanna Vogelsong is a longtime friend of Jill and a seasoned traveler who brings warmth, humor, and curiosity to every trip. Follow Deanna here:

• Insta: @kingbirdsings
• TikTok: @sweetTakes

About the Show: True Travel Talk takes you around the world with real stories, honest tips, and inspired itineraries — from family adventures to faraway escapes, always grounded in connection and curiosity.

Follow along on Instagram: @truetravelcrew & TikTok: @truetravelcrew

Executive Producer & Host: Jill Bohaboy Produced by: Collective Change Communications — Kelly Sakalas & Jeni Keeler

Travel & Experience Highlights:

• TAASA Luxury Lodges & Camps
• Global Partners For Development
• Killi Seasons
• Hoopoe Safari
• Pastoral Women’s Council
• Ngare Sero

About Our Guest: You can follow Josie Russell and see her photography here

• Insta: @josierussell10
• TikTok: @josie.r1

About the Show: True Travel Talk takes you around the world with real stories, honest tips, and inspired itineraries — from family adventures to faraway escapes, always grounded in connection and curiosity.

Follow Along on Instagram: @truetravelcrew

Executive Producer & Host: Jill Bohaboy Produced by: Collective Change Communications — Kelly Sakalas & Jeni Keeler

10. Looking to escape the big city? Head to Cusco, Peru. In this episode, Jill and her friend and neighbor, Amy, share another chapter of their Peru adventure – from a tipsy train arrival to an almost-disastrous departure.

They cover Cusco’s hidden gems and lessons learned, including the Santo Domingo Convent, the iconic 12-Angle Stone, and the vibrant San Pedro Market, along with their honest take on where to stay. Plus, hear about their Pisco tasting, dinner at the renowned Cicciolina restaurant, and favorite local bites.

Warm hospitality, stunning architecture, unforgettable culture – tune in to hear why Cusco belongs on every Peru travel itinerary. Travel & Experience Highlights:

• Stay at the uniquely beautiful Palacio Nazarenas, A Belmond Hotel
• Grab lunch at LIMO overlooking the Plaza de Armas
• Learn about, taste and try your hand at making pisco cocktails at Museo Del Pisco.
• Enjoy a delectable dinner, even when you’re already stuffed, at Cicciolina Restaurant
• And here’s the recipe for Lomo Salto

For pictures of this trip and to follow along our next adventure, follow us on Instagram: @truetravelcrew

About the Show: True Travel Talk takes you around the world with real stories, honest tips, and inspired itineraries — from family adventures to faraway escapes, always grounded in connection and curiosity.

Executive Producer & Host: Jill Bohaboy Produced by: Collective Change Communications — Kelly Sakalas & Jeni Keeler

9. Sometimes the best trips aren’t planned around big landmarks – they unfold through shared stories, good meals, and the people you travel with. In this episode, Jill joins California winemaker and friend Bill Williamson for a three-day road trip through France’s Loire Valley, filled with unforgettable winery visits, river views, perfect meals, and plenty of laughter.

From a goat-filled gas station to tastings with local winemakers and dinners overlooking the Loire, this is travel at its best: slow, joyful, and rooted in friendship.

Travel & Experience Highlights

Day One: Sancerre → Blois

• Sancerre for Savingnon Blanc at Château de Crezancy (arranged by phone with Nicolas Chevreau)

• In Blois, stay at Fleur de Loire - 44 rooms + suites, Loire views, historic hospitality
• Dinner at Amour Blanc (at the hotel)

Day Two: Vourvray → Chinon

• Vourvray: Marc Brédif Chinin Blanc tasting, intimate floral setting
• Lunch: Chinon sidewalk cafe; light salads, narrow streets
• Tastings:
  • Angelliaume - cave tasting with quirky signs
  • Bernard Baudry - formal Cab Franc tasting
• Dinner: Bro’s Restaurant - courtyard dining

Day Three: Blois

• Lunch + Shopping: Art de la Table, Cheese tasting at La Passion du Fromage
• Dinner at Le Médicis, final foie gras, fresh marshmallow dessert with sunset over the Loire

About the Guest: Bill Williamson is an Australian-born winemaker who moved to California with his wife Dawn in 1980 and went on to found Williamson Wines in Sonoma’s Dry Creek Valley. He oversees the vineyards and winemaking for more than 45 award-winning, direct-to-consumer wines and is known for making wine feel accessible, joyful, and meant to be shared. As he says, “I grow good grapes, make good wine, and I share it with friends.” Find more ways to engage with Williamson Wines here.

About the Show: True Travel Talk takes you around the world with real stories, honest tips, and inspired itineraries — from family adventures to faraway escapes, always grounded in connection and curiosity.

Follow Along on Instagram: @truetravelcrew

Executive Producer & Host: Jill Bohaboy Produced by: Collective Change Communications — Kelly Sakalas & Jeni Keeler