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

Wardrobe Malfunctions: The Dress Did Her Dirty

Let’s talk wardrobe malfunctions because if it can go wrong, it will go wrong. We’re talking red wine spills, last-minute crotch sew-ups, duct tape...(yes, actual duct tape), and everything in between. We’ve seen it all. We’ve fixed it all. And now we’re telling the stories.
 
If you’re planning a wedding, deep in the Pinterest spiral, or just need a laugh at someone else’s bridal fashion emergency, this one’s for you. Real weddings, real behind-the-scenes stories from planners who’ve kept the dresses and the day from falling apart. Literally.

Megan Explores Sandals St. Vincent

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 megan@daretodreamtravelwi.com
 

Destination I Do’s & Don’ts

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.

It's a Toast, Not a Roast

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? MaybeDo we have some hilarious, real-life stories to share? AbsolutelyAre those stories packed with actually helpful advice? You already know
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.

Swiss Alps & Spritzes: Jen in Switzerland

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.

From Shutdowns to Chaos: The COVID Wedding Era

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.
 
 
 

Put a Ring on It with Bryn Mawr Jewelry Co

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! 
 
#ThePlannersPassport #WeddingPodcast #JewelryDesign #CustomEngagementRing #BrynMawrJewelryCo #ChicagoJeweler #PushPresent #AnniversaryGifts #LuxuryJewelry
 

Welcome Sean Denny of Luxe Productions

Ever wonder what it means to work in wedding production? This week, our podcast welcomes Sean Denny, the Director of Events and Production Designer for Luxe Productions which is based in Chicago. From his humble beginnings working as a DJ during college to traveling the country and producing high-profile, star-studded events, Sean's journey has us wishing he hadn't signed so many NDAs and could share more dirt. 
Listen now to hear Sean's story, from his early passion for music to his transition into the wedding production industry in NYC. He reveals the challenges and excitement of creating unforgettable experiences for clients, including the intricacies of producing glamorous events and we'll even try to manifest his dream of organizing a culturally rich Lebanese wedding. And in true Jen and Megan fashion, we'll try to encourage some celebrity shout-outs – will Ryan Reynolds show us some love?
Tune in for an engaging conversation with Sean Denny as we dive into the fascinating world of wedding production.
 
Learn more about using Luxe Productions for your next event HERE. 

East Coast vs. Midwest Weddings: Jen v. Megan

East Coast vs. Midwest Weddings: Jen v. Meg
In this episode of The Planner’s Passport, it’s the first-ever Jen v. Megan showdown—though, let’s be real, no one's actually swinging. Megan loves the classic East Coast wedding format, while Jen—well, she’ll happily plan a Midwest wedding, but deep down, she’s ready to flip the whole wedding day schedule on its head. From dancing between courses to rigid timelines, we’re breaking down traditions and questioning the status quo. Tune in for a fun, slightly competitive, but mostly just entertaining debate on East Coast vs. Midwest weddings!

Megan Travels to Sandals Montego Bay - with Kathy!

This week on The Planner’s Passport, Megan heads back to Jamaica and visits Sandals Montego Bay! Along for the ride is her mom Kathy who's always up for a piña colada and some antics on the beach. 
 
Will Jen's favorite OWM make it back to shore after his ill-advised windsurfing adventure? And how do Megan and Kathy take advantage of the baller butler service they received from their new best friend Marvin? 
But most importantly, do they get in the tub?
 
You have to listen to find out so grab a Red Stripe and push play to hear all about their great times in Jamaica!
 
Interested in learning more about Sandals Resorts? Contact Megan for free travel planning service to any of these beautiful Caribbean destinations. 
 
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