Five questions for Becky Tilson Squires

Becky Tilson Squires visited Walt Disney World for the first time as a middle schooler, and it was love at first trip. Today, as the founder of Tilson Travel, she gets to share that feeling of wonder by planning dream trips for her clients, not only to the house of Mickey Mouse, but to destinations worldwide. South chatted with her about the best travel outfits, her favorite weekend getaway and how to survive a family vacation.

What are the in-demand vacation destinations for summer?

Hawaii and Disney consistently, year after year, whether it’s family vacations, multigenerational vacations or grandma and grandpa are taking their kids and then their grandkids. We’ve got a lot of honeymooners, and the first place they think of is Hawaii. Both of those destinations are always at the very top of the list. And there’s plenty to do. You can go back to Hawaii and Disney and not do the same thing twice. You can have a different experience every time. 

Traveling with family is fun, but it can also be challenging. Any advice for staying sane?

Don’t over-schedule your trip down to the last second. Especially with Disney, it’s hard to do, because you have Fast Pass (ride reservations) and dining reservations. But allow for free time; schedule some late mornings or early evenings so that you’ve got free time to relax at your leisure. Go on a run, go to the spa. Allow the parents and the grandparents to do their own thing. Let the kids play at the pool while you just hang out by the pool. Especially for those introverted family members or travelers, like myself. I need that time to be by myself and not go, go, go all the time.

What about travel outfits? What can you wear that’s both comfortable and stylish?

Items that breathe and aren’t too tight, like linens. I love linen pants. Those I will live in. Something that’s not so fitted and constricting, especially on the plane, (because) your hands will get swollen or your feet will get swollen. Wear clothing that is breathable and relaxing, not too clingy and uncomfortable. And that washes well. Layers too. If you’re worried about whether it will be too chilly or too warm on the flight, then you’ve got layers to take on and off.

What is your personal approach to travel?

It’s the saying about the cobbler’s kids having no shoes. I am my own worst travel agent. I’m thinking of everyone else and planning everyone else’s travel, but then when it comes to my own I kind of forget about it. But I like to have it about 50/50. Half of my trip is planned. We know what we’re doing. We know we’re going to see the main sights. We’re going to eat at the main places, making sure that we’re getting into the destinations where the locals live, where they eat, and really experiencing that destination. And then the other half of the time I like to keep open and flexible for either spontaneity or just free time to relax. This is time to recharge the batteries. I’ve done vacations for myself that are just go, go, go, and halfway through I’m just beat. So I like to have flexibility and free time scheduled as well.

Do you have a favorite travel spot?

I love the Biltmore estate in Asheville, North Carolina. It’s such a lovely, long-weekend destination. It’s a beautiful home. Every time that we go, we see something different, we learn something different about that period in which they lived, or they’ve opened a new wing of the house. They just opened a new village there, with its own dining and winery and tasting room and shops. Their botanical garden is just gorgeous, (especially in) the spring because of the tulips and everything that’s blooming. And it’s very relaxing. Once the house closes, you go back to your hotel and grab dinner and hang out on the Adirondack chairs and read a book. It’s a nice, cozy place.

By Julie Cope Saetre // Photography by Stacy Able