Olivia McKerley is the kind of travel advisor who’s been planning vacations since she could hold a pencil—literally. As a kid, she played “travel agent” for fun, and thanks to a lifetime of travel that started at a very early age, she turned that childhood hobby into a career she genuinely loves. Now, with 12 years of professional travel planning experience, Olivia brings both expert knowledge and real-life family insight to every trip she designs.
Before stepping fully into the travel world, Olivia was an elementary school teacher—an experience that sharpened her gift for listening, guiding, organizing, and (let’s be honest) keeping things running smoothly. She holds three college degrees from Augusta University and is also a homeschool mom to two kids, ages 9 and 13, which means she understands exactly what families need when traveling with tweens and teens: the right balance of fun, downtime, and unforgettable experiences.
Olivia is especially passionate about Disney destinations. She visits Walt Disney World multiple times every year and has stayed at every resort except one—making her an incredibly well-versed guide for families hoping to make the most of their Disney vacation. Her personal favorites? Disney’s BoardWalk Inn and Wilderness Lodge. She’s also visited Disneyland and Southern California multiple times (one of her family’s favorite places to explore), and fun fact: she even danced at Disneyland once as a kid—a memory that still makes her smile and probably explains why she believes Disney magic is very real.
Olivia has also visited Aulani and explored the beauty and adventure of Hawaii, and cruising is another one of her specialties, with over 20 cruises under her belt. She’s a Platinum Castaway Club member with Disney Cruise Line, which means she knows Disney cruising inside and out—from ship differences and stateroom options to the best itineraries and onboard tips. She’s also sailed with Carnival and Royal Caribbean, giving her a well-rounded understanding of what makes each cruise line a great fit for different families.
When it comes to all-inclusive vacations, Olivia has done the homework firsthand—visiting nine Sandals and Beaches Resorts and earning her status as a proud Sandals Silver Elite Travel Advisor. She’s also explored a wide range of all-inclusive resorts across Mexico and the Caribbean, always adding new destinations and experiences to her toolkit so she can keep offering fresh recommendations and the best possible matches for her clients.
Today, Olivia specializes in helping busy families—especially those with tweens and teens—plan vacations that feel exciting, easy, and completely worth the time away. And when a trip turns into a multi-generational adventure with grandparents, grandkids, and everyone in between? That’s her favorite kind of magic.
Certifications: Disney College of Knowledge, Certified Sandals Specialist, Universal Orlando Resort Specialist & Royal Caribbean