Custom luxury & family travel planning
Every trip is designed around your travel style, priorities, and pace—whether you’re planning a milestone celebration, a multi-generational vacation, or an effortless getaway.End-to-end itinerary design
I manage every detail, including flights, accommodations, transfers, and carefully selected experiences, creating a cohesive and well-paced journey from start to finish.Concierge-level support before and during travel
You’ll have a dedicated point of contact throughout the planning process and while you’re traveling, offering guidance, adjustments, and peace of mind whenever needed.Personalized recommendations and preferred partnerships
Trips are informed by first-hand experience and a trusted global network, with added amenities and exclusive benefits when available.
Designed for independent travelers in their 20s, this itinerary blends iconic landmarks with authentic local experiences—from watching master glassblowers in Murano and leather artisans in Florence to exploring world-famous museums, enjoying traditional Tuscan and Roman cuisine, and discovering lively neighborhoods after dark.
Designed for couples in their 50s, this itinerary offers the ideal blend of scenic exploration, authentic Hawaiian experiences, and time to simply relax. With six nights on Kauaʻi and seven nights on Maui, you'll enjoy each island at an unhurried pace, returning home with incredible memories and feeling truly refreshed.
This Costa Rica vacation perfectly combines the country's two most iconic experiences—the lush rainforests and volcanic landscapes of Arenal with the golden beaches and laid-back surf culture of Tamarindo—creating an unforgettable adventure for 4 adults and 5 teenagers.
Hi, I'm Kerry Henley, founder of K. Henley Tailored Travel Co. For nearly two decades, I ran a Montessori school in upstate New York — an experience that taught me to anticipate every detail and balance structure with creativity.
Now I bring those same skills to crafting travel: luxury family vacations, romantic escapes, European itineraries, beach getaways, and Disney trips, all designed around who you are and what you want to remember. I handle the logistics — flights, transfers, tours, insurance, special requests — so you can simply be present.
At heart, travel is about the connections made along the way, and I'm here before, during, and after your trip to make those moments possible.
With years of experience planning complex family travel and high-touch itineraries, I design trips that feel effortless, personal, and thoughtfully paced. Every journey is planned as if it were my own.
Real feedback from families and couples I've had the pleasure of planning trips for — verified reviews from Google, Travel Leaders Network, and Facebook.
"Kerry was absolutely amazing in planning our family vacation! Every place she recommended and every tour she arranged was incredible. She truly took the time to understand what our family would enjoy, and because of her, we had the best time and made so many wonderful memories. When we unexpectedly had an issue with the hotel that the couple whose wedding we were attending had selected for their guests, Kerry immediately stepped in to help. She quickly found us a beautiful, clean, and comfortable hotel and even helped other family members who needed to make the transition as well. Kerry went above and beyond throughout our entire trip. Her attention to detail, responsiveness, and genuine care made such a difference. We are so grateful for everything she did and would highly recommend her to anyone planning a vacation!"
"Kerry Henley did an outstanding job planning our trip to Italy. Her attention to detail and organization made the entire experience seamless from start to finish. She thoughtfully tailored our itinerary to match our interests, ensuring we had the perfect balance of structure and flexibility. We especially appreciated how she allocated our time across Venice, Florence, and Rome. Thanks to Kerry's expertise in event planning and scheduling, our trip was not only stress-free but truly unforgettable. I would highly recommend her to anyone looking for a well-curated and personalized travel experience."
"We had such a wonderful experience working with Kerry while planning our trip to St. Thomas. We were not sure where we wanted to spend our Spring Break with two young children and Kerry was fantastic at looking at our timing, budget and ideal vacation. She suggested a few places and helped us narrow down our destinations with educated suggestions. Everything from the hotel to the excursions and restaurant recommendations were tailor made for our family. We felt very supported throughout the process which is definitely going to keep us coming back for future trips!"
"We recently returned from a one-week family trip to Paris and London, and Kerry did an amazing job. She created an itinerary that covered all the major highlights while still keeping the pace comfortable and not too tiring. We were pleasantly surprised by how much we were able to see without ever feeling rushed. She also did a fantastic job balancing activities that kept our kids engaged while allowing us time to relax. Everything was thoughtfully organized and flowed seamlessly throughout the trip. We can't wait to plan our next vacation with her!"
"Kerry was very easy to work with. She gave us a detailed itinerary and lots of great options for entertainment and dining. Will definitely be working with her again in the future!"
"Kerry did an excellent job of organizing our trip to Costa Rica! She picked great excursions and travel accommodations. We highly recommend!"
"Kerry was extremely helpful and insightful when it came to providing options that fit our vision and budget. The itinerary package we were sent was super informative and an excellent guide to help us navigate the town we visited. So thankful!"
kerry@khenleytailoredtravel.com
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