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 WE HELP
We plan Caribbean family vacations for Black families who want everyone together... without the stress.
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?
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.
Q: How much does it cost?
A: We charge $125 for your Vision Session. The fee will go toward any additional service fees that may arise from our discussion. You'll pay separately for your travel costs (flights, resort, activities). We'll give you a full breakdown before committing you to any booking. Note: Travel costs may fluctuate until a deposit has been made with the tour company.
Q: Do you only plan trips to the Caribbean?
A: Yes and No. We can book anywhere Worldwide. However, we specialize in Caribbean destinations because we know them well and can create the best experience for your family.
Q: What if we've never traveled with the whole family before?
A: That's exactly who we help! We'll walk you through everything and make sure the trip works for everyone.
Q: How far in advance do we need to book?
A: Ideally 3-6 months, but we can work with tighter timelines depending on availability.
