The Planner’s Passport - Wedding Planners, Travel Agents, Decades of Stories

This week on The Planner’s Passport, we’re heading south.

We’re joined by Kelley Kohler of Haviland Events, a boutique wedding planning and design firm based in Charlotte, North Carolina. After hearing our East Coast vs. West Coast episode, Kelley had a few thoughts, especially after Jen questioned whether North Carolina even counts as “the South.” (Spoiler: it does. And she came ready to defend it.) 

Kelley brings over a decade of experience planning stylish and meaningful weddings across the country and abroad. She started Haviland Events in Chicago before returning to her Southern roots, and now designs elegant, timeless celebrations for thoughtful couples throughout the Southeastern United States.

In this episode, Kelley shares what Southern wedding traditions couples still embrace today, how hospitality shapes wedding planning in the South, and how she helps her clients create personalized, unforgettable wedding weekends. Plus, we talk about her vintage china collection and where she thinks “the South” actually begins.

This week, we’re taking you behind the scenes at the WedMKE wedding show in Milwaukee! We had an incredible time hosting a booth, connecting with real couples (and a few very enthusiastic moms), and catching up with some of our favorite vendor friends, like Milwaukee Airwaves and Two Birds Event Group.

Of course, it wouldn’t be a Planner’s Passport episode without a bit of chaos and laughter. Jen may or may not have developed a very on-brand crush on a DJ (stay tuned—you won't want to miss it).

Throughout the event, we answered tons of real wedding planning questions about wedding planning and how to navigate all the big decisions that come with putting together your dream day.

Whether you're newly engaged, deep into wedding planning, or just gathering ideas, this episode is packed with real advice, helpful tips, and lots of that behind-the-scenes perspective we love sharing with you. If you're planning a wedding, this is a must-listen! We're giving away some of our best free wedding planning wisdom to help you feel confident, organized, and excited about your big day.

This week on The Planner’s Passport, Megan takes us to St. Vincent and the Grenadines, where work and play collided in the best way. She went for business (because Megan’s idea of time off is working from a beach), but she still found time to soak up the island magic—bat cave adventures, new friendships (channeling Jen, of course), and a Sandals resort experience that seriously impressed her.

She shares why this Sandals property just might be her favorite (and no, she doesn’t say that about all of them), how to customize your Sandals stay to your personal spice level, and the hidden gems of St. Vincent that most travelers miss.

If you're planning a honeymoon, romantic escape, or a Caribbean getaway, this episode is full of honest insight, destination inspiration, and travel tips you’ll want to take with you.

Tune in now and escape to St. Vincent and the Grenadines with us.

Want help planning your own Sandals adventure? Reach out to Megan of Dare to Dream Travel at [email protected]

Are you dreaming of saying “I do” with your toes in the sand? This week, Jen and Megan are diving into all things destination weddings—the good, the complicated, and the cocktails.

From breezy beach vows to mountain-top ceremonies, we’re breaking down the real pros and cons of planning a wedding away from home. Should you hire a local planner? When does it actually make more sense not to? And what sneaky logistics are often overlooked?

This episode is your passport to understanding the full picture—from legal requirements to travel stress, and everything in between.

So grab your sunnies, pour yourself something tropical, and press play. It’s time to find out if a destination wedding is really your perfect match.

This week, Megan and Jen dive into the only thing that can throw a perfectly planned wedding timeline into chaos: toasts.

Are we a little crabby about it? Maybe

From rogue speeches to timing disasters, we’re spilling the tea on how to give a wedding toast that’s unforgettable for all the right reasons. Tune in to hear our insider tips, pet peeves, and what makes a toast land or totally flop.

Hit play and get ready for laughs, insight, and all the behind-the-scenes goodness you didn’t know you needed.

Jen is back from Switzerland and filling Megan in on everything from skiing in Davos to sipping Aperol Spritzes in Zurich's 75 degree weather (in March!). The two dive into the magic of solo travel, the Swiss food scene, the surprise weather swings, and yes, Jen cried again.

With plenty of signature Jen and Megan banter, this episode is full of laughs, travel inspo, and behind the scenes moments from Jen’s seven day adventure through Zurich, Lucerne, and Davos.

If you have ever considered a solo trip to Europe, this might be the sign you were waiting for. Grab your headphones and a glass of wine because we are back and ready to roam.

See more about Marktgasse Hotel HERE.

It’s hard to believe, but it’s been five years since the world changed overnight. This week on The Planner’s Passport, Megan and Jen take a look back at 2020 to 2022, revisiting what it was like to navigate the industry through shutdowns, endless wedding reschedules, and the chaos of reopening.

From the early days of postponements and pivots to the overwhelming demand that followed, they share their personal journeys, how COVID impacted their businesses, their clients, and the wedding and travel industries as a whole.

What did survival look like in the events world? How did they adapt? And what lasting effects are still felt today?

Join them for a candid conversation about the challenges, resilience, and lessons learned over the past five years.

This week on The Planner’s Passport, we’re joined by Jill Freeman of Bryn Mawr Jewelry Co., a Chicago-based boutique she owns with her husband, Scott.

Jill takes us behind the scenes of custom jewelry design, spills on her biggest pet peeves, and shares how she and her team work closely with couples—not just to create the perfect engagement ring, but to build a lifelong relationship where they can keep you iced out forever. 

From engagement rings to anniversary gifts, wedding bands to push presents, Jill and her team are all about helping couples mark life’s most meaningful moments with pieces that are as special as their story.

Tune in for all the sparkle, some expert insights, and of course—a little behind-the-scenes tea! 

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