This week on The Planner’s Passport we’re joined by a very special guest, Grace from Tarot D’Amore.

Grace is a soulful tarot and movement specialist who brings wisdom, intuition, and heart to everything she does. She offers tarot readings for weddings and beyond, guiding people to connect with themselves, their relationships, and the deeper meaning behind life’s milestones.

In this episode, she shares her story, how she began blending tarot with love and ceremony, and the powerful ways she helps people navigate big transitions with clarity and compassion.

It’s soulful, fascinating, and full of insight. You don’t want to miss this one.

It’s one of the questions we get asked the most, and this week we’re finally talking about it. After years of watching couples up close on one of the biggest days of their lives, we’ve seen just about everything—moments that melted our hearts, and a few that made us quietly wonder how the night (or the marriage) would end.

In this episode, we’re sharing some of the stories that stuck with us, the red flags we’ve noticed along the way, and the subtle signs that reveal how two people really work together when the pressure’s on. It’s honest, funny, and maybe a little unfiltered, but that’s what makes it good.

If you’ve ever wondered what planners really think after seeing hundreds of weddings from behind the scenes, this one’s for you.

 

This week, we talk about… well, everything and nothing at all, which is basically our specialty.

We catch up on Megan’s time up north Wisconsin, one of Jen’s former make-out sessions, and why you should always walk up the hill when your boyfriend tells you to. (Spoiler: proposals happen on hills.) We get into upcoming travel plans, pooping on vacation, Groupon purchases, Mexican food cravings, and of course, JAMAICA! Come travel with us.

SPECIAL ALERT: If you’ve been thinking about advertising with us, now’s your moment. Get in at the basement level and grow with us because this elevator is going up.

So no, it’s not nothing. It’s everything. It's hilarious. And it’s very us. Press play.

 

This week, we’re joined by Jesse Lyon of Lyon Mental Health—a therapist, dream interpreter, and hilarious human who somehow made talking about the subconscious feel like a party. We get into the weird and wonderful world of wedding dreams (yes, those anxious ones with missing dresses and runaway grooms), including Megan’s cake dream that—spoiler alert—wasn't really about cake at all. Jesse breaks down what our dreams are trying to tell us during high-stress seasons like wedding planning, how therapy can help us navigate the chaos, and why he thinks your mental health team deserves a seat at the vendor table. It’s insightful, entertaining, and one of our favorite convos yet.

 

Lyon Mental Health

@lyonmentalhealth

This week on The Planner’s Passport, we’re talking timelines—specifically, how much time you really need to plan a wedding. Whether you're stretching things out over 18 months or sprinting toward an 'I do' in six weeks, there are perks and pitfalls on both sides.

Longer planning timelines might sound like a dream (hello, options), but with time comes the temptation to overthink everything. Shorter timelines force quick decisions, streamline the process, and reduce waffling—but they also come with logistical curveballs and fewer available vendors.

We break it all down: from decision fatigue to vendor availability, budget impact to emotional whiplash. And in true fashion, we absolutely go off the rails at least once, possibly more. You already know.

Whether you're a type-A planner or a last-minute lover, this one’s for you.

 

This week on the pod, we’re joined by one of our OG listeners —  Heather Cook Elliott! To say that Megan and Jen are as mutually obsessed with her as she is with us? A massive understatement.

Heather is a Milwaukee-based wedding and portrait photographer whose work is rooted in real connection, thoughtful storytelling, and capturing people as they truly are. She’s the kind of person who shows up fully behind the camera and in life, and we absolutely adore her.

In this episode, we dive into Heather’s origin story, what it’s like building a creative business with soul, and why we all can’t stop giggling through this whole conversation. Spoiler: Heather’s coming with us to Jamaica. Are you??

 

 Tune in for major bestie energy, industry insight, and a whole lot of love.

 

This week, we’re joined by the wildly talented and hilariously cheeky Rachal A. Duggan, the creative genius behind Rad Illustrates. Known for her signature butt drawings (yes, you read that right), Rachal is an illustrator, author, and workshop leader who brings her one-of-a-kind style to everything from comics to custom wedding art.

We dive into how Rachal started drawing butts, what it’s like being a creative vendor on a wedding day, and the unexpected chaos of live event sketching.

From editorial and branding illustrations to teaching private drawing workshops, Rachal does it all and somehow makes it all hilarious. Tune in for puns, laughter, and an honest peek behind the (butt) curtain of wedding day artistry.

Follow her work on Instagram and TikTok @radillustrates.

Last week, Jen popped off about moms (and no, Megan still does not agree with her).

This week? Megan’s the one telling it like it is. And honestly? We're. Here. For. It.

She’s in her villain era, y’all. We’re talking wedding industry awards and how (surprise!) a lot of them are paid for. Not saying the people winning don’t deserve the spotlight, but it’s worth knowing there’s usually money behind that shiny badge. Transparency matters, and Megan’s not holding back.

Tune in! Why? Because it’s so fun when Megan spills the dirt.

This week’s episode is all about moms.  

To be clear, Megan does not sign off on any of this. This is 100% Jen’s story arc... from superhero to supervillain wedding planner.

Now, Jen actually loves most moms. But in her experience, a few bad apples spoiled the bunch so much that she no longer works with parents unless they’ve been fully vetted.

But this episode isn’t just about mom drama (although yes, a few wild stories are shared). It’s really meant to help moms navigate the modern wedding planning journey. A lot has changed since their own wedding days... and let’s just say, some of them struggle with that. So this one’s for you, moms. We’re here to help so that you don't become a Momzilla.

Oh! We also spend a solid 15 minutes talking about “John Smith” (name changed to protect the extremely attractive but not-so-innocent boy everyone had a crush on in high school).

You don’t want to miss it.

We’re fangirling a little harder than usual this week, because our guest isn’t just TikTok-famous—he’s also one of Jen’s former grooms… twice. (Ah, the joys of COVID-era weddings.)

Marco Braun—aka @marcosfunhouse—joins us to share the story of his two celebrations, what it was like planning during a pandemic, and how he accidentally became the internet’s vintage recipe king. Oh, and did we mention that Hilary Duff bought him and his husband their registered china after he went viral for being the world’s biggest Lizzie McGuire fan?

We talk about love, weddings, internet fame, and yes… a very passionate discussion about mayonnaise. It’s hilarious, heartwarming, and everything you didn’t know you needed today.

🎙️ This Week on the Podcast: We're Going Tropical, Baby! 🌴

Pack your sunscreen and questionable swimwear—we're taking this podcast to The Bahamas and want YOU to come with us! In this episode, we spill the (piña colada-flavored) tea on our upcoming getaway to Sandals Royal Bahamian. Think snorkeling with sea turtles (or at least aggressively friendly fish), late-night karaoke that may cause permanent secondhand embarrassment, and tropical drinks with umbrellas that are fancier than our actual wardrobes.

We're giving you the inside scoop on what it's like to party podcast-style in paradise, how to snag your spot on this sandy adventure, and why your mom, best friend, or mildly chaotic partner absolutely needs to come too. It’s happening November 30–December 3, and it’s going to be legendary… or at least mildly sunburned and extremely fun. 🌞🎤🌊

 

Want more info or to get your room on hold?

Reach out to Megan at megan@daretodreamtravelwi.com or check out our trip page at http://www.daretodreamtravelwi.com/join-us-bahamas.html

 

See you on the beach! 

Megan & Jen

This week, Jen’s in Sonoma County to facilitate a bachelorette party , but let’s be real, she also used the trip to scout the region for future travelers (because of course she did).    From sipping sparkling wine at Iron Horse Vineyards to inhaling the best vegan quiche of her life at Little Saint in Healdsburg, this episode is packed with wine country magic and mild chaos. She stopped in Bodega Bay for oysters, explored Calistoga for those cute Northern California vibes, wandered around The Barlow in Sebastopol, and managed to fit in a date—because you know how Jen rolls. This one happened with a sommelier who lives in a van (Megan would like you to know it’s technically a camper). Oh, and there was vomiting in the bathroom (not Jen, chill).    Tune in for travel inspo, planning tips, wine recs, and everything you should (and definitely shouldn’t) do on your next Sonoma County trip.

We love a confident couple who says, “We’ll totally have time!” … until they realize photos, champagne, and nerves say otherwise.

In this episode of The Planner’s Passport, we’re diving into one of the biggest wedding day struggles — the timeline. We’re breaking down why you’re probably not giving yourself nearly enough time, how long things actually take, and why your vendors aren’t being dramatic when they say that dinner is going to take 90 minutes. 

We’ll talk about how to build a timeline that keeps the day moving (without rushing it), why buffer time is your new best friend, and the secret to avoiding the dreaded “we’re running late” announcement.

If you’re planning a wedding — or you just love hearing planners rant about timelines — this one’s for you.

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.

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.

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

 

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 Do we have some hilarious, real-life stories to share? Absolutely Are 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.

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! 

 

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

 

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. 

The wedding industry is, at the end of the day, a for-profit industry. That might surprise some couples, but it’s true. This week, Megan and Jen are pulling back the curtain on how pricing works in the wedding world and why it makes sense.

Here’s the thing: just because you’re planning a wedding doesn’t mean vendors should automatically discount their services. Yes, weddings are joyful, and yes, we’re thrilled to celebrate with you — but professionals in this space are running businesses that take time, skill, and energy to deliver amazing results. And that’s something worth valuing.

The reality is simple: experience and expertise matter. The longer someone has been doing this and the better they are at it, the more their services are worth. That’s true in every profession. And just because something has a higher price tag doesn’t mean it’s unfair or inflated.

Think about it this way — would you want someone walking into your workplace and telling you to cut your paycheck in half because they “feel like it”? Probably not. Weddings are no different.

Do you agree or disagree? Tune in this week to hear more!

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!

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

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.)

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. 

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      

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!

This week, Jen and Megan are diving into all things catering—a topic every wedding planner and engaged couple needs to know about. And yes, they’re spilling a few new pet peeves along the way (you’re welcome!).    They’ll break down the pros and cons of in-house catering versus bringing in your own caterer, sharing behind-the-scenes insights on how to navigate this key decision. Plus, they’re dishing on some of the coolest, most creative catering setups they’ve pulled off with their partnered caterers—because who doesn’t love a good grazing table or a fresh oyster station? Of course, in true fashion, they’ll also veer off into some hilarious side tangents because they just can't help themselves.

This week, Megan and Jen are driving (see what we did there?) into one of the most critical (and often overlooked) aspects of wedding planning—transportation! We’re sharing all the dos and don’ts of booking and coordinating transportation for your wedding day. Whether it’s getting the wedding party to the venue on time, managing shuttles for guests, or navigating last-minute logistics, we’ve got you covered.

Packed with practical tips and real-life examples, this episode is a must-listen for couples, wedding planners, and anyone looking to ensure a smooth, stress-free day. Because let’s face it—transportation can make or break your timeline! 

Planning a wedding is like walking a tightrope—balancing the perfect day while hoping no one goes off the rails. Let’s face it: wild wedding guests are inevitable. In this episode of The Planner’s Passport, we’re spilling WTF moments—bridesmaids eating it on stairs, rogue underwear sightings, and a DJ stuck on "Panda" by Desiigner. Oh, and injuries? Plenty.

We’ll also share how wedding planners attempt to keep things under control, from handling open-bar sprinters to disaster-proofing the day. Whether you’re wedding planning or just here for the train wrecks, this episode delivers the juiciest antics, hard-earned tips, and pure chaos.

Tune in for the laughs, the cringes, and the WTF moments that’ll make you wonder how weddings even happen. (Spoiler: planners deserve awards and therapy.)

It’s that week between Christmas and New Year’s—when no one knows what day it is, wine is flowing, and schedules are out the window. We might be a little all over the place, but we’re still diving into the pros and cons of planning a holiday wedding!

If you’re recently engaged or in the early stages of wedding planning, this episode is full of helpful insights to guide you in choosing the perfect date for your big day. From planning for additional labor charges to the secret holiday you should choose if you don’t want anyone to come to your wedding, we’re covering… well, most of it (do we get a little off topic? Absolutely—but that’s part of our charm).

Whether you’re dreaming of a winter wonderland wedding or curious about the logistics of a July 4th celebration, tune in to hear our tips, thoughts, and a few laughs as we break it all down (and Jen drinks too much Viking's blood...yes, you read that right).

After years of planning weddings and events, Megan and Jen have figured out which rules matter most and they are not budging. In this episode, they dive into the non-negotiables of wedding planning: the details that make or break an event, the mistakes couples should avoid, and the standards they will always defend. If you are planning a wedding and wondering what is really worth it (and what is not), this episode is packed with honest advice, expert tips, and strong opinions.

In this episode of The Planner’s Passport, Jen takes us on a rollercoaster trip through Munich and Prague, where she wandered through magical Christmas markets like a festive queen, drank her weight in Glühwein (a true talent), attended a European hockey game—because culture comes in all forms—and went on so many educational tours she could practically give one herself. 

Of course, no trip is complete without a little chaos: she cried in the streets of Munich, found a lover in Prague (yes, you read that right), and hit up McDonald’s not once, but twice—because sometimes, comfort food just calls your name.

If you’re into solo travel, chaotic adventures, or just want to hear what happens when you mix romance, history, and that much mulled wine, this episode is for you. Pack your bags—or at least your headphones—and come along for the ride!

BTS: Rachael Steacy Events

In this episode of The Planner's Passport, we’re joined by our very first guest, Rachael Steacy, the powerhouse behind Rachael Steacy Events. If you’ve ever wondered what makes a great wedding planner worth their weight in gold, this conversation is for you.

We go behind the scenes of wedding planning, sharing stories about turning bold and creative visions into reality. From jaw-dropping successes to the “never-do-that-again” moments, we reveal the highs and lows of crafting one-of-a-kind celebrations. Along the way, we dish out invaluable tips on avoiding common wedding pitfalls and keeping the magic alive under pressure.

Whether you’re a bride, groom, wedding planner, or just someone fascinated by the wedding world, this episode is packed with laughs, insights, and inspiration. Be sure to stick around until the end—you won’t want to miss the fun!

Don't forget to subscribe and email us at theplannerspassport@gmail.com to share your own stories that could be featured on a coming episode!

 

Grab a Caribbean cocktail and come along with Megan as she relives her latest adventure in travel to Beaches Turks and Caicos! The whole family tags along on this adventure down to this salty island where she explores Beaches largest all-inclusive resort on the heart of Grace Bay Beach. We'll meet some turtles, hunt for Drake and drink more pina coladas than one woman should ever consume in six days on the beach. Join us to hear more about this beautiful island nation and it may inspire you to put your own toes in the sand here in the near future. 

Megan and Jen are airing out their biggest pet peeves in the world of wedding planning. From demanding guests to those infamous Type A bridesmaids, they're not holding back. Tune in to hear their candid rants about the little things that drive them up the wall and advice for staying on a wedding planner's good side. It's a vent session where they're glad you can't see their eyes rolling!  

Join Megan and Jen as they take you behind the scenes, sharing their wildest stories from their early days as newbie planners 14 years ago. From unexpected mishaps to losing a toenail in the line of duty, they give you an unfiltered look at the unpredictable world of event planning - laughable tales that show that everyone starts somewhere (and even as pros, they still are learning and growing as planners every day)!

Join us for our launch episode as we take a walk down memory lane and share our own stories on how we got our start in the wedding industry as wedding consultants and what has driven us to also dip our toes in the travel industry. Everyone starts somewhere and here's the back story of our story!

This week, travel talk is back as Megan takes us on a journey back to Jamaica

Join us as she shares her family vacation to Beaches Negril on the famous Seven Mile Beach, one of the top all-inclusive resorts in Jamaica. From stunning Caribbean beaches and unforgettable sunset views to unexpected travel mishaps and family adventures, this trip had it all. We talk about Beaches handled the bumps with care, why going with the flow is key when traveling, and how even a perfectly imperfect vacation can create unforgettable family memories. If you’re planning a trip to Beaches Negril or just love real stories about family travel, this episode is for you!

 

Interested in planning your own family vacation to Beaches Negril or Beaches Turks and Caicos? Reach out to Megan for free travel planning services or check out her YouTube Channel, The Sandals Insider to hear more! 

 

Dare to Dream Travel

www.daretodreamtravelwi.com

megan@daretodreamtravelwi.com

 

#beachesnegril

This week we’re diving into one of the biggest wedding guest debates: kids or no kids? We break down the pros and cons of having little ones at your wedding, how to figure out if your kids are actually invited, and what you should do (and plan for) if you decide to make your wedding kid-free. Whether you’re planning your own wedding or packing up the stroller for someone else’s big day, this episode has the tips, stories, and advice you need.

This week, we’re talking about the one thing you can’t control on your wedding day: the weather. From sudden storms to sweltering heat, we’ve seen it all—and we’re sharing our own weather disaster stories to prove it.

We’ll cover what couples often forget when planning for outdoor ceremonies and receptions, why guest comfort should always come first (hint: no one wants to sit in 90-degree heat), and the practical steps you can take to weather-proof your wedding.

Whether you’re dreaming of a summer garden party, a lakeside celebration, or a cozy winter wedding, this episode is packed with tips to help you stay prepared and keep the day running smoothly, rain or shine.

Let’s be real—your hair and makeup team can make or break your wedding morning vibe. In this episode, we’re chatting about why you shouldn’t wait to put down that deposit (yes, glam squads book up fast!), how to speak up during your trial so you actually love your look, and why the big day beauty is always, always about the bride (sorry Aunt Karen). We’ll share funny stories, real talk, and planner-approved tips so you can walk down the aisle feeling like the star of the show—because you are.

Ever wonder what really goes on behind the scenes of a wedding? In this laugh-out-loud episode, two seasoned wedding planners spill the tea (and maybe a little champagne) on some of their most outrageous confessions from the job.

From sneaking sips of prosecco during the ceremony to shamelessly devouring the couple's untouched appetizers (look, someone had to eat them), no story is off-limits. Oh — and yes, one of us definitely had to poop in the bridal suite. You'll have to listen to find out who.

It’s unfiltered, a little unhinged, and 100% real. If you’ve ever thought wedding planning was all peonies and Pinterest boards... buckle up.