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 ~