The Planner’s Passport - Wedding Planners, Travel Agents, Decades of Stories
Join Jen and Megan every week as they spill the tea on over a decade of wedding planning adventures, share their journey into the travel business, and dish out advice on living your best life. Based in the Midwest, these two professional wedding consultants and travel gurus have been kindred spirits since the late ’90s and are ready to bring you inside the crazy world of weddings sharing hilarious stories of things they have witnessed, lessons they have learned and a few tips along the way for vendors, brides, grooms, moms, dads and honeymooners alike! Tune in to hear these two peas in separate pods give you a behind-the-scenes look at their lives as wedding planners, discuss the ins and outs of being small business owners, and hopefully inspire you to break out of your routine and explore the world. Megan’s Businesses Include: Dare to Dream Travel - Booking Sandals and Beaches vacations, honeymoons and family travel / @dtdtravelwi Dare to Dream Weddings - Wedding Planning Services in Milwaukee, Wisconsin / @dtdweddingswi Jen’s Businesses Include: A Fresh Event Travel - Wedding Planning Services in Chicago, Illinois / @afresheventco We Roam Solo - Travel planning services for Solo Travelers Worldwide / @weroamsolo
Episodes

7 days ago
7 days ago
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.

Wednesday Mar 19, 2025
Wednesday Mar 19, 2025
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.

Wednesday Mar 12, 2025
Wednesday Mar 12, 2025
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

Wednesday Mar 05, 2025
Wednesday Mar 05, 2025
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.

Wednesday Feb 26, 2025
Wednesday Feb 26, 2025
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!

Wednesday Feb 19, 2025
Wednesday Feb 19, 2025
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.
Dare to Dream Travel
Sandals and Beaches Resorts

Wednesday Feb 12, 2025
Wednesday Feb 12, 2025
This week, we’re tackling one of the most controversial wedding topics—tipping. Who gets tipped? How much? Is it really optional? (Hint: No.)
If you’re getting married, this episode will help you figure out who and how to tip your wedding pro team. If you’re a wedding vendor, this is a good listen too—because we know you have thoughts.
Jen and Megan break down what they tell their couples to do, share the biggest tip they ever received (which was “look both ways before you cross the street”), and try to answer the age-old question: Can you leave a review in place of a tip? (No.)

Wednesday Feb 05, 2025
Wednesday Feb 05, 2025
This week we’re joined by Brit Grosenick, founder of Happy Joy Candy Co., a Milwaukee-based company bringing the fun with home-spun cotton candy, drink glitter bombs, and more sweet surprises.
We’re diving into the real side of being a wedding entrepreneur, the highs and lows of running a business, and why couples are loving these playful treats at their weddings. If you’re a bride, groom, or wedding planner looking to add a little extra fun to your big day, this episode is packed with ideas, inspiration, and behind-the-scenes magic.
Reach out to Brit Here! Happy Joy Candy Co.

Wednesday Jan 29, 2025
Wednesday Jan 29, 2025
This week on The Planner’s Passport, Jen takes us to the stunning Big Island of Hawaii! She explores Kona and Hilo, drives around the island, and visits incredible spots like the Krishna Cow Sanctuary in Papaikou, the Green Sand Beach at Papakōlea, and the Black Sand Beach at Punalu‘u.
Jen also indulges in a private dinner with Chef Ippy, owner of Nāpua at Mauna Lani, and shares tips for creating your own Hawaiian escape. Don’t miss this episode packed with breathtaking sights, local flavors, and travel inspiration!
Locations Highlighted:
Krishna Cow Sanctuary
Green Sand Beach at Papakōlea
Black Sand Beach at Punalu`u
Chef Ippy of Nāpua Restaurant

Wednesday Jan 22, 2025
Wednesday Jan 22, 2025
This week, we’re chatting with Dan Nowak, the owner and “Tall Guy” behind Brazen Standard, the parent company of Tall Guy and a Grill, The Crafted Tavern, and The Dessert Cart, all based in Milwaukee, Wisconsin. Dan shares how he turned his passion for food and events into a mega brand that is now a staple in the wedding and event industry. From crafting unique wedding catering experiences to creating unforgettable menus for corporate events, Dan reveals the secrets behind his growth and how he continues to raise the bar in hospitality.And, because we know you love it, he also dishes his biggest wedding pet peeves (yes, we know what you're here for).Whether you’re a planner, a vendor, or just love hearing behind-the-scenes stories from the event world, you won’t want to miss this episode! Tune in now for a mix of inspiration, laughs, and a custom drink recipe!

Jen & Megan
Wedding wizards turned travel queens.
Hang with Jen and Megan for weekly stories from their decades long careers as wedding planners and their new adventures as travel consultants. With over 600 weddings under their belts and more coming each season, they are sure to have stories that will shock even the most seasoned wedding veteran.
If you have a wedding or travel related story that you would like shared on a future episode, or if you are interested in coming on as a vendor guest to share your own stories, please email us at theplannerspassport@gmail.com.
Podcast Music Credit:
Mehul ShaRma & Limujii - Travel