Travel Advisor
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.
Kiley plans trips for travelers in Morton, IL and beyond, from cruises and all inclusive resorts to Europe, Disney, and group getaways. Most of the planning happens by phone, email, or text, so wherever you are, it fits your schedule. Working with Kiley never costs more than booking on your own, and you'll have a real person in your corner the whole way.
Kiley Smith
I specialize in crafting memorable getaways for families and couples to beautiful Caribbean destinations.
Morton, IL
Let’s get started
Pick what feels closest to your dream trip. Kiley will reply within one business day.
CRUISEOcean & river cruises across every line.
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ALL-INCLAll-inclusive resorts in the sun.
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EUROPEEuropean adventures, tailored to you.
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ROMANCEHoneymoons, anniversaries, and destination weddings.
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DCLDisney Cruise Line sailings.
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SANDALSSandals & Beaches getaways.
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TRAVELNot sure yet? Tell us what you're dreaming up.
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Here’s what’s part of every trip Kiley books. Have a special request? Just ask, Kiley loves to tailor things to your family.
Custom itinerary planning
Booking changes & advocacy
Celebration planning (birthdays, anniversaries, honeymoons)
Group / multi-family coordination
Day-of trip support
Ongoing price monitoring
Trips I love to plan
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.
Training & credentials
Royal Caribbean Master of Adventure
College of Disney Knowledge
Sandals Elite Advisor
Carnival Learn & Earn Certificate
NCLU Associate
Outrigger Expert Advisor
Prefer to chat?
Let’s talk it through!
Same questions as the quote form, just easier. Answer a few things about your dream trip and Kiley will pick it up from there.
Where I love to send people
How we’ll work together
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.
Frequently asked
Family & Couples Vacation Specialist including cruises, all-inclusive resorts, European escapes, honeymoons, and group travel.
