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

Vendor Spotlight: Grace of Tarot D'Amore

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.

Can you tell if a couple is going to make it?

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.
 

Wedding Day Timelines 101: Why Everything Takes Longer Than You Think

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.

The Wedding Industry: We're Here to Make Money

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!

Non-Negotiables: The Wedding Hills We'll Die On

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.

Travel to Beaches Negril: Our Perfectly Imperfect Vacation

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

Kids or No Kids? The Great Wedding Debate

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.

Weather or Not: The Big Day Must Go On

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.

A Wedding Planner’s Guide to Hair and Makeup

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.

Tea for Two: Wedding Planners Spill All

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.