For generations, the vacation home has been a mark of affluence. These properties often become a substantial part of their owners’ estates, financially and emotionally, leading to the questions: Do family members want to preserve the property as a true “family” vacation home? And if so, how?
The attraction to doing so is usually evident. The vacation home is likely in a beautiful location. The owners’ children and grand-children may have grown up spending time there each year, suffusing the property with cherished memories. To use language from The Cycle of the Gift, a family vacation home is the most concrete and perhaps most powerful form of a “gift with spirit.”
The challenges to preserving a family vacation home are also substantial. Real estate is illiquid and can be expensive to maintain. Jointly-held property brings with it legal complexity. Most complex of all are the interpersonal issues of managing such property.
Competent counsel can help owners of the property foresee and address many complexities, by identifying the entity in which to hold the property, the method for assessing costs to owners, ways to protect the property from various types of liability, and practices for making joint decisions about everything from renovations to decorations.
However, to adapt Peter Drucker’s famous saying that, “Culture eats strategy for breakfast,” I would say that culture eats structure for dinner. Not even the most creative documents will preserve a shared vacation home if the family does not attend to its human relationships—its “family culture.”
What, then, does the family culture look like that increases the likelihood of successful, enjoyable preservation of a family vacation home? And how does a family inculcate and strengthen that culture?
Culture is formed of habits and beliefs. Habits and beliefs arise, in turn, from modeling behaviors and communicating expectations. Most simply, if you want to achieve a certain result, then lead that life. If you want to preserve your vacation home, then you need to live a way of life that supports its preservation. That means practicing these habits yourself. It also means expecting others to practice them.
What does this life look like? Here I’m going to borrow from the 100-Year Families Study, a study of the cultures of families who have successfully passed on a major family enterprise through three generations of family ownership or more. These enterprises often involve operating businesses. Their practices apply directly to families who are managing other assets together, such as a vacation home. Some of the key elements of “100-Year” family culture include
Learning and sharing what you learn with your family members.
Developing the habit of regular and transparent discussion of financial matters within your family.
Trusting others and earning their trust.
Modeling the expectation that all family members will, in their own ways, contribute actively to the family.
Modeling the expectation that all family members will, in their own ways, contribute actively to the community or the world.
These are just a few of the habits that foster success in family enterprise generally. There are other habits that we have seen prove instrumental for the specific task of preserving a family vacation home:
Make sure that everyone shares in the duties of ownership, so that no one feels burdened as the sole “steward”—or entitled to an outsized voice in the property’s management.
Tell stories that connect the family members to the property. Why this place? What was here before us? What special events took place here? A great way to “tell” stories is by decorating the property with pictures of the past and present.
Cultivate a sense that the property is special, even sacred, something worth family members’ devoting their time and money to. One way to do that is through holding a reunion there each year that also recognizes important milestones in family member’s lives. Some families write their children’s names or their own names on a certain wall of the estate, creating a record of the family for decades or even centuries. Others decorate the home with special items purchased or made by family members. Likewise, some family vacation homes have guestbooks that stretch back decades, in which now-elderly family members can see records of their own visits as children.
Remind yourselves that the family and the property are not the same. Cultivating this habit of mind will allow your family to deal with the time when someone doesn’t want to visit or asks to be bought out.
Be a good host: practice the habit of being enjoyable for others to spend time with, and help them be enjoyable to each other, so that they are grateful for the time together rather than feeling it to be a burden. This habit is especially important vis-à-vis significant others or spouses. If the spouses of younger family members enjoy visiting the property, they will bring their children, laying the foundation for a shared future.
This, then, is the way to make a vacation home a true family legacy: live the sort of life that cultivates its preservation.
These efforts to preserve a family vacation home embody several paradoxes. First is the paradox in the title of this article: a family “vacation” home entails a lot of work. Second is this: a family should come to see the vacation home as special, as giving the family a sort of identity—and they should also see the family as separate from the home, and so be able to preserve relationships with family members who don’t partake in its ownership or use. Third, underlying all else, is this paradox: a family that wants to preserve its vacation home should see the property as priceless—and hence worthy of dedication—and at the same time each owner of the property should feel that his or her “share” is worthless, and so not be looking ahead to “cashing out.” Perhaps all three of these paradoxes are themselves expressions of the importance that sharing a vacation home can hold for family members—as something that transcends the realm of what money can buy.
I hope that these comments on family culture allow you to reflect on your own family and to ask whether such a culture already exists and, if not, whether it is like to take hold. If not, then the best thing you can do may be to temper your hopes about this sort of legacy and to speak directly with your children about whether eventually to sell the property. I have seen many instances in which parents’ willingness to raise this possibility has proven a great relief to the rising generation.
For most families, whether it is good to try to preserve a family vacation home is an open question. There are benefits, and there are costs. The most practical matter, then, may be first to step back from the question of what you’re trying to preserve and how to preserve it, and to reflect honestly on the question of who you and your family are and whether this challenge is right for you.
 See Hughes, Massenzio, and Whitaker, The Cycle of the Gift: Family Wealth & Wisdom (New York: Bloomberg, 2014), especially Chapters Two and Twelve.
 Readers can find more detail on operational choices families make to preserve a vacation home in Jamie Forbes’ chapter, “How Can You Preserve a Beloved Family Vacation Home or Estate,” in Wealth of Wisdom (New York: Wiley, 2018). Forbes’ article draws on his own family’s century-long experience of owning and managing the island of Naushon, off the coast of Cape Cod.
 For a description of the characteristics of enterprising families, see Dennis Jaffe, The Resilience of 100-Year Family Enterprises: How Opportunistic Innovation, Business Discipline, and a Culture of Stewardship Guide the Journey Across Generations (Boston, MA: Wise Counsel Research, 2018).