Plan Multi-generational Family Vacations Without the Stress-These six families show us how it’s done.

A bucket list multi-gen honeymoon

Destination: Senegal

Number of travelers: 14

Trip organizers: Monique Waters, 37, and Norris Williams, 36

Waters: While planning our honeymoon, we thought, Why not Africa? Then we asked, What if we brought friends and family? So we invited relatives and close friends for a nine-day trip to Senegal. Lacking the expertise to plan it ourselves, we turned to Henderson Travel Service, the first Black-owned travel agency in the U.S. They customized our itinerary based on our interests, from art and dance to tribal connections.

Williams: For my mother, visiting Africa was a lifelong dream. She described it as pure joy, love, and gratitude. For me, the highlight wasn’t just the experiences—it was seeing our family grow closer. The trip strengthened our bond in ways we never expected.

Multi-gen honeymoon tips

Gauge interest. They sent a survey to gather input on preferences and concerns.

Centralize information. A trip website covered costs, itinerary, hotels, and vaccine details.

Offer payment flexibility. Instead of one large sum, they set up a four-part payment plan.