Transgenerational wealth transfer (TWT), the transfer of wealth from one generation to the next, is expected to grow significantly in the coming years. The longevity of wealthy families, which is far from secure, depends on its success. Although TWT poses a challenge for most families, their methods to prepare for it have remained underexplored, making this study timely and relevant. This research focuses on families with substantial wealth who own their family offices (FOs), also known as single-FOs. If FOs are said to contribute to successful TWT, so is philanthropy. Hence, by understanding how families approach philanthropy, intending to perpetuate their engagement, and how FOs support their efforts, I aimed to create a roadmap to help FOs guide families toward a successful TWT. I demonstrate that the family’s philanthropic journey consists of four sequential phases that each generation navigates. I argue that socioemotional wealth, which is deeply rooted in the philanthropic journey, connects philanthropy to TWT. My findings show that it is critical for the FO to adopt a stewardship attitude to prepare the family for a successful TWT and encourage and facilitate the engagement of the members of the next generation (NextG), which is recognised to be challenging. A three-step framework is proposed. Also, my findings suggest that in addition to recalibrating and aligning its support to the younger generation’s objectives, a sound balance between the family’s traditions and renewal brought by the NextG must be struck. The study contributes to both the fields of philanthropy and FOs. It intends to open new future research avenues and provide valuable insights for practitioners and FOs to tailor their advice and support to the family and its members.