Hi, I'm
FAMILY & COUPLES VACATION SPECIALIST
Based in Morton, IL
I specialize in crafting memorable getaways for families and couples to beautiful Caribbean destinations.
Hi! I'm Kiley. I'm a stay-at-home mom to two sweet girls, wife to my wonderful husband of nine years, and dog mom to three pups that definitely keep life interesting. Our house is busy, loud, and full of love.
My passion for travel didn't come from taking extravagant vacations growing up. Quite the opposite, actually. Our big trips were piling into the car before sunrise for a St. Louis Cardinals game or spending a weekend in Wisconsin Dells. Looking back, those are some of my favorite memories.
When I was 11, cancer took my dad. Losing him at such a young age taught me something I wish no child had to learn: tomorrow isn't guaranteed. Those simple road trips became some of my most treasured memories because they were time we got to spend together.
That's why I love travel so much. To me, it has never been about staying in the fanciest resort or taking the most expensive vacation. It's about slowing down, putting your phone away, and making memories with the people you love.
Now that I'm a parent myself, I understand that lesson even more. Kids grow up so fast, life gets busy, and it's easy to keep saying, "We'll do it next year." My hope is to help families realize they don't have to wait for the perfect time. Whether it's a weekend getaway, a Disney vacation, or the cruise you've been dreaming about, those moments together are worth it.
At the end of the day, I'm not just helping you book a vacation. I'm helping you create memories that your family will still be talking about years from now. Because long after the trip is over, it's the time you spent together that you'll remember the most.

Let's Get Started

Every advisor has a story. Here's a look at the trips, places, and people that shaped how Kiley plans yours.




This 9-night Southern Caribbean itinerary I recommend offers a rich blend of vibrant culture and peaceful relaxation across Perfect Day At CocoCay, Bahamas, Cabo Rojo, Dominican Republic, Willemstad, Curacao, and Oranjestad, Aruba.


Here's what's part of every trip I book. Have a special request? Just ask — I love to tailor things to your family.
My goal is to handle all the details of your family or couples getaway, allowing you to simply anticipate a well-planned trip.
— Kiley


Tell Kiley who's traveling, when, and what makes a vacation feel magical for your family.

Receive personalized resort, cruise, or destination options curated to fit your style and budget.

From booking to boarding pass, you'll have an expert in your corner the entire journey.
What does Kiley specialize in?+
Does it cost extra to book with Kiley?+
How quickly will Kiley respond?+
Where is Kiley based?+
Tell Kiley about your vacation vision. Pick the path that feels easier — chat it out or fill the form.
Have a quick conversation with Kiley's assistant. Same questions as the form, but easier — and you can ask anything along the way.
Prefer to reach out directly? KILEY.SMITH@CCTCAGENT.COM
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