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The Legacy Journey Experience

You’re not just planning a vacation — you’re preserving a legacy.
TravelWithKey presents four unforgettable 6-day journeys designed for multigenerational Black families seeking deeper connection, heritage, and healing.

 

Whether you're walking ancestral paths in St. Croix or dancing bomba in Loíza, each trip blends meaningful culture with rest, joy, and togetherness.

Legacy Journeys

Where Black Families Reconnect Through Culture, Courage & Caribbean Joy

I’m so glad that I was able to experience Echoes of Freedom with my grandson. It gave us a chance to really connect and learn together while relaxing and enjoying our vacation.

~ Mary Graves ~

Finally a vacation where my whole family is in the picture. We were welcomed with open arms as we participated in local cultural festivities. My wife and daughter were even gifted their beautiful headwraps to remember our time reconnecting as a family.

~ The Jones Family ~

Not Sure Which Journey Fits Your Family?

Take our quick Trip Fit Quiz or send us an inquiry — we’ll help you choose the legacy journey that best fits your family’s story.

Join the Legacy Circle.

Be the first to hear about new Legacy Journeys, get insider Caribbean travel tips, and receive family travel inspiration straight to your inbox.

We don't spam. We build Community.


As a Legacy Circle member, you'll get:

  • 🌴 Early access to trip announcements (before they sell out)

  • 🥘 Exclusive stories about Caribbean culture and cuisine

  • 👣 Tips for planning meaningful, stress-free family travel

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Edkesha Anderson

edkesha.anderson@yahoo.com

An Independent Agent of WorldVia Travel Network

+1 (334)-216-7166

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