Stop Stressing Over Family Travel. We'll Handle It.
TravelWithKey provides done-for-you Caribbean and legacy travel planning for families and professionals who don’t have the time, bandwidth, or desire to manage complex trips.
I specialize in multigenerational travel, milestone trips, and culturally rooted experiences where coordination, decision-making, and logistics become overwhelming.
TravelWithKey steps in when travel stops being fun and starts feeling like a job — handling strategy, booking, and execution so clients can focus on the experience, not the planning.
This service is NOT for DIY planners, price shoppers, or people looking for endless options. It’s for clients who want one clear plan, handled professionally, from start to finish.
WHO THIS IS FOR
TravelWithKey is best for travelers who:
-
Are planning a Caribbean or legacy-focused trip
-
Are coordinating more than one traveler, generation, or decision-maker
-
Want professional planning instead of DIY research
-
Are ready to move forward with a clear plan
If you’re still exploring ideas or comparing options, my content and guides are the best place to start.
HOW WE HELP
TravelWithKey steps in when travel stops being fun and starts feeling like a job — handling strategy, booking, and execution so clients can focus on the experience, not the planning.
Here's what you get:
You want to take your whole family on a trip. But planning for multiple generations feels impossible. Different budgets. Different mobility needs. Different ideas of "fun." And you're the one stuck figuring it all out. What if someone else could handle the details so you could just show up and enjoy?
HOW IT WORKS
All planning begins with a paid Vision Session. This ensures alignment, clarity, and a focused plan — before any bookings are made.
All planning begins with a paid Vision Session. This ensures alignment, clarity, and a focused plan — before any bookings are made. Starting at $125 planning fee + travel costs
The Jefferson Family
"We had four generations on our cruise and everything was seamless. TravelWithKey made it unforgettable."
Carla T.
"TravelwithKey's AllFamTM took the stress out of planning our family reunion. We just showed up and had fun."
The Martins
"The best family trip we've ever had. From the hotel to the excursions. Everything was handled."
ABOUT TRAVELWITHKEY
My name is Edkesha "Key" Anderson
I started TravelwithKey because I believe Black families deserve travel experiences that honor our roots, our elders, and our joy.
Too many of us feel disconnected... from our heritage... from each other... from the places our ancestors called home. Travel can change that.
Whether you're reconnecting in the Caribbean or gathering your family for a reunion, I'm here to make it easy, meaningful, and stress-free.
Let's plan something beautiful together.
— Key, Founder of TravelwithKey
READY TO PLAN YOUR FAMILY TRIP?
Book a Vision Session and let's talk about where you want to go.
