Samantha Aylward

Hi there! I’m Sam, and I’m so happy you’ve found your way here.

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Since 2024, I’ve been helping families, couples, and groups create unforgettable vacations that fit both their dreams and their budgets. I truly believe that everyone deserves time to step away from the everyday, reconnect with the people they love, and make memories that last a lifetime. Helping make that happen is one of my greatest joys.

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By day, I work as a Director of Treasury, which means I understand firsthand the importance of balancing incredible experiences with real-life budgets. That perspective allows me to help clients maximize the value of their vacations without sacrificing the magic.

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My heart has always belonged to Disney destinations. As a former Cast Member in the 2007 Disney College Program, Disney has been woven into my story for many years. My family visits regularly, and each trip teaches us new ways to experience the magic while making the most of our vacation investment. Whether you’re dreaming of a value-packed family getaway or a luxury stay with views of Cinderella Castle from Disney’s Polynesian Resort, I can help create a vacation that feels uniquely yours.

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These days, I’m also loving the excitement and adventure of planning Universal vacations, helping families discover everything these incredible destinations have to offer.

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As someone who comes from a large family, I have a special appreciation for multi-generational travel. Whether you’re coordinating grandparents, cousins, friends, wedding guests, or a group getaway, I enjoy bringing together all the moving pieces to create a trip everyone can look forward to. From split-stay itineraries and family reunions to girls’ weekends, golf trips, and destination celebrations, I love finding the perfect fit for every traveler.

 

When I’m not planning vacations, you’ll usually find me spending time with my husband, Nick, and our two daughters, Bailey and Autumn. We love traveling together, discovering new destinations, road-tripping with our senior pups, Belles and Chance, and making memories wherever the journey takes us. We’re also a dance-loving family, spending many of our evenings at the studio enjoying ballet, tap, and the wonderful community we’ve found there.

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Travel has taken us to some incredible places, from the beaches of Jamaica and Turks & Caicos to countless family adventures closer to home. We’re always dreaming about the next destination, including an upcoming castle stay in Scotland to celebrate our 15th wedding anniversary.

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No matter where your next adventure leads, I would be honored to help you plan it. Together, we’ll create a vacation filled with unforgettable memories, a little extra magic, and plenty of reasons to keep wishing, wandering, and exploring.

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✨ Welcome to Wish & Wander Travel Collective — where every journey begins with a wish and becomes a story worth telling.