Penny Cooper
Meet Penny Cooper
Founder & Lead Advisor | Embrace The Magic Travel™
Disney Destination Expert · Family Travel Advocate · Concierge Planning
Hi, I’m Penny — a mom, creative entrepreneur, and passionate Disney vacation expert who believes in the power of everyday celebration and the joy of well-planned family travel.
Since 2012, I’ve helped hundreds of families plan thousands of trips to experience the magic of Walt Disney World, Disney Cruise Line, and other family-friendly destinations — without the stress. I founded Embrace The Magic Travel™ to serve busy families who crave connection but don’t have time to manage all the details. I bring calm confidence, methodical planning, and heartfelt support to every vacation we create — so your family can focus on making memories, not managing logistics.
Whether you’re organizing a trip that includes toddlers, teens, and grandparents — or treating your loved ones to fireworks, fine dining, and VIP tours — I’ll help you plan it with a little more style and a lot less overwhelm.
Professional Credentials
You’re not just working with someone who loves Disney — you’re working with someone who studies it, lives it, and partners with the industry’s best.
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Founder of Embrace The Magic Travel™, planning family vacations since 2012
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Certified in Walt Disney World, Disney Cruise Line, Universal Orlando, and more
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Member of ASTA and CLIA, with access to Virtuoso amenities through sister company C Pinnacle Travel and its affiliation with Gifted Travel Network, a Virtuoso member agency.
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Recognized speaker, panelist, and mentor in the Disney and family travel industry
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2024 Hamilton Travel Agency Best of Award, plus multiple Magellan Awards for Innovation and Business Strategy (with Magic Made Simple, for ETM’s award-winning client emails)
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Specialty focus on Disney Cruise Line Concierge, resort Club Level, Deluxe Resorts, multigenerational travel, first-time Disney families, and families with mobility or sensory needs
“I regularly complete on-site visits, advanced training, and partner education so I can offer truly up-to-date insight — from park openings to dining reservations, and everything in between.”
Traveler Reviews
100% Recommended on Virtuoso · 7 Reviews
“Penny always makes our trip planning so easy! We tell her what we want and it’s done! Great communication and follow thru.”
Virtuoso traveler review · December 2021
“Helpful, informative, and knowledgeable! Penny saved us hours of time researching everything. She answered all of our questions, made reservations, and saw to the specific details we required in our rooms.”
Sharon D. · Royal Caribbean Cruise
“She is always courteous, efficient, patient, and helpful! She pays attention and remembers details about us even when we don’t!”
Rose Ann S. · Walt Disney World and Universal Orlando
What I Love to Plan
- Disney Cruise Line Concierge sailings
- Walt Disney World Club Level and Deluxe Resort stays
- Florida and California theme parks
- Family cruises
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River cruises for families, couples, and groups
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All-inclusive resorts designed with families in mind
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Alaskan land tours and cruises
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Hawaiian island resorts and sailings
Because ‘knowledge is power’, we have dedicated hundreds of hours of online, classroom and in the field training for our portfolio of preferred partners. We educate ourselves so we can give you our expert advice and experience.
Orlando
College of Disney Knowledge
Universal Orlando Resort Specialist
Legoland Resorts Specialist
SeaWorld Parks & Entertainment Specialist
Destinations
Orlando Specialist
Hawai’i Destinations Specialist
Jamaica Specialist
Cruise Lines
Royal Caribbean University of Wow Expert+
RCCL Autism Friendly Certification
Norwegian Cruise Line Master’s Degree
Celebrity Cruise Line Five Star Travel Partner Princess Cruise Line
Resorts and All-Inclusives
Atlantis Ambassador
RIU Hotels & Resorts Specialist
Certified Sandals Specialist
Where I’m From — and Who I Serve
Born and raised in South Carolina, I now live in Lawrence, New Jersey, and serve families across the country.
I understand both Southern hospitality and Northeast hustle — and how family travel logistics vary by region. That means I’m uniquely equipped to help clients from all walks of life. Many of the families I work with come from:
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New Jersey and Pennsylvania – where I serve busy professionals and families in Mercer County and beyond
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South Carolina and the Southeast – where my Southern roots keep me connected to local families and traditions
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Nationwide – because the desire for magical, meaningful travel knows no zip code
Wherever you’re from, I’ll treat you like family.
More Than A Planner
Beyond travel planning, I’m also a writer, speaker, and creative entrepreneur. I own Pirate Mom Penny, LLC, and I’m the co-founder of Magic Made Simple™, a media brand that helps other travel advisors serve their clients more personally and efficiently.
I’ve contributed to platforms like The Disney Moms, Scouting WDW, and I Heart WDW, helped lead conversations about storytelling in travel, and created tools that simplify the experience for both clients and advisors.
A Peek Into My Life
I homeschooled my son from kindergarten through high school — and today he’s a proud Clemson graduate, an Eagle Scout, and an avid fan of all things Philly sports.
When I’m not planning trips or mentoring other advisors, you’ll find me…
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At book club with friends
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Scrapbooking memories of our family adventures
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In ministry with my local church
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Adding sprinkles to whatever’s baking in the oven
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And always — dreaming about our next vacation together
I believe every day is a day to celebrate. So yes, the good china and the fancy napkins are just part of a Tuesday.
As Seen On
Frequently Asked Questions About Planning with Penny
How do I start planning with Penny?
Request your personalized vacation proposal or schedule a call using the buttons on this page. Penny will learn about your family, your travel style, and what matters most, then design a plan around you.
Does Penny charge a planning fee?
Penny offers concierge planning packages for families who want a fully managed, personalized experience. You’ll find details on her services page, and she’ll recommend the option that fits your trip best.
Where is Penny based, and does she plan for families outside New Jersey and South Carolina?
Penny is based in Lawrence, New Jersey, with roots in South Carolina. She plans vacations for families nationwide.
What does Penny specialize in?
Disney Cruise Line Concierge, Walt Disney World Club Level and Deluxe Resorts, multigenerational trips, first-time Disney families, and families with mobility or sensory needs.