Whether they order gourmet meals at the country club or join a sailboat racing competition at the marina, your neighbors are not simply relaxing on the weekend. They are refining. Their leisure pursuits are deliberate—balancing personal fulfillment with social currency. Your neighbors are strategically expanding their knowledge, sharpening their skills, and deepening their connections.
For those newly arrived, the question is not just how to enjoy the weekend but where—and with whom. A well-chosen pastime signals an understanding of this rarefied world’s rhythms and rituals. What, then, are your neighbors doing this weekend? More importantly—where will you be?
Here’s What Your Neighbors Are Doing This Weekend
Vintage Car Collecting
Those who curate vintage car collections preserve history, elevate craftsmanship, and enjoy a community that lauds automotive excellence (a lost art, if you ask us). You might think that collecting classic cars is solely for the ultra wealthy, but any coastal homeowner with a sizeable garage can engage.
Whether a 1957 Ferrari 250 Testa Rossa or an Aston Martin DB5 speaks to you, your classic car collection will likely appreciate in value. Consider it an investment in a diversified portfolio just as much as it is an investment in social capital.
How to Start
Start with a single rare model that aligns with your taste and interests. Consider hiring a personal curator or attending elite auctions like RM Sotheby’s.
Sailboat Racing
To be sure, sailboat racing is an adrenaline boost—perhaps the most thrilling hobby on this list. It blends skill, competition, and tradition on the open water—arena where wealthy individuals test their mettle against both nature and one another.
While the super rich compete in the America’s Cup, even those new to the sport can experience the excitement of cutting through waves at regattas in Palm Beach, Newport, or St. Barts. You don’t have to own a Wally or Swan to join in. Plenty of clubs offer fractional ownership or access to seasoned crews willing to take on a promising new sailor.
How to Start
If you’ve never raced before, charter a yacht with an experienced crew and learn the fundamentals. From there, joining an exclusive yacht club like the New York Yacht Club or St. Francis Yacht Club—will connect you with the right circles.
Art Collecting
The majority of the world’s most influential individuals are serious collectors. They understand that the right painting or sculpture can elevate their social standing while bolstering their bank account.
Whether walking away from Art Basel with a blue-chip Warhol or acquiring several works by an emerging artist in an avant-garde Paris gallery, the key to art collecting is knowing where—and how—to buy. Wealthy individuals don’t just step into a gallery and purchase a new piece. They cultivate relationships with gallerists, curators, and museum directors. In doing so, they ensure that their collections reflect both personal taste and institutional prestige.
How to Start
Begin by attending major art fairs like Frieze, TEFAF, and The Armory Show. Work with an art advisor to refine your collecting strategy. Invest in high-end museum memberships like MoMA’s Director’s Council or the Tate’s International Council. Membership often grants early access to coveted works and invitations to exclusive collector events.
Horse Racing
Owning a thoroughbred costs, but it equates to legacy, strategy, and a seat at one of the most elite tables in the world. The ultra-wealthy don’t just watch the Kentucky Derby or Royal Ascot. They own the horses that either compete or contribute to incredible racing bloodlines.
How to Start
Partner with a reputable bloodstock agent to identify promising young horses. Syndicates allow first-time investors to get involved at a lower entry cost, while full ownership is the ultimate prestige.
Creating Your Own Wine or Spirit Label
Francis Ford Coppola and Brad Pitt have turned their passion for winemaking into highly successful brands, and many wealthy individuals are following suit. Whether a biodynamic vineyard in Napa or a bespoke mezcal distillery in Oaxaca, crafting a personal label is both a creative and strategic endeavor.
How to Start
Work with a respected local vintner or distiller to create your first release before investing in land. Hosting exclusive tastings ensures your brand gains recognition among collectors.
Skiing in Other Countries
Not quite a coastal hobby, but we could not leave skiing off this list. For the ultra rich, skiing is as much about where you ski as it is about the sport itself. Courchevel, St. Moritz, and Aspen are the undisputed social hubs where wealthy individuals gather. The après-ski scene is where introductions are made, alliances formed, and deals finalized.
A private chalet at the right resort is not just a winter escape—it’s a passport into a world where status is defined as much by your skiing ability as by your guest list.
How to Start
Start by either learning to ski yourself or attending events in locales beloved for their slopes. If you choose the former, a personal trainer can help refine your technique. If you prefer the latter, start with Aspen’s X Games! To fully immerse yourself, consider investing in a private chalet with access to VIP services.
Golf
Arnold Palmer once said, “Success in golf depends less on strength of body than upon strength of mind and character.” He wasn’t wrong. The majority of top business leaders play golf—not just for leisure, but because it remains one of the most effective ways to form connections that matter.
How to Start
Membership at a highly selective club is essential. If your swing needs work, private coaching will ensure you are not only present but also competitive.
Vintage Watch Collecting
Much like vintage car collecting, acquiring fine timepieces is an art—one that signals appreciation for craftsmanship, history, and heritage. A rare Patek Philippe, a limited-edition Rolex Daytona, or a vintage Audemars Piguet is absolutely iconic.
Unlike mass-produced luxury items, the finest vintage watches are rare. They often pass through generations or surface only at the most exclusive auctions. A well-chosen timepiece is a discreet yet powerful symbol of status.
How to Start
Begin by studying the histories of major watchmakers. Understand what makes certain models truly exceptional.
Work with a trusted dealer or attend elite auctions such as Phillips or Christie’s to acquire your first piece. Consider joining collector groups or private watch salons where collectors exchange insights.
Hosting a Fundraiser
A well-orchestrated fundraiser is an opportunity to shape conversations, build influence, and solidify your standing in your community—all while making a difference for causes you truly care about. Coastal homeowners don’t simply donate; they host.
From an intimate cocktail reception benefiting the local arts scene to a grand gala supporting marine conservation, a fundraiser at your coastal home should reflect both your values and your ability to bring together the right people.
How to Start
Partner with a respected nonprofit or cultural institution to align your event with a cause that resonates. Work with an event planner to ensure that every element—from the guest list to the menu curated by a Michelin-starred chef—embodies sophistication and intention. The majority of high-level social networks are forged over shared philanthropy, so this one of the most powerful ways to integrate into your new community.
Gardening Like Martha Stewart
Whether tending to rare orchids, curating a collection of heirloom roses, or cultivating a biodynamic vegetable garden, gardening is an expression of refinement, patience, and a deep appreciation for nature.
Unlike normal people who rely on a team of landscapers, the super rich often garden themselves. (Of course, they work closely with master horticulturists.) From the impeccably manicured parterres of Palm Beach to the wild, sculptural beauty of Montecito’s coastal gardens, these private landscapes reflect the taste and vision of their owners.
Just look at Martha Stewart’s stunning gardens!
How to Start
Begin with a dedicated space—whether a rooftop garden, a private greenhouse, or a sprawling estate—and work with expert landscape designers to bring your vision to life.
Attending Gallery Openings, Museum Exhibitions, and Art Fairs
Understanding (and collecting) art signals intellect, discernment, and cultural fluency. From blue-chip galleries in Chelsea to private previews at Art Basel, these events are where wealthy individuals connect, discuss investment-worthy pieces, and build relationships with artists, curators, and collectors.
How to Start
Attending panel discussions and exclusive museum salons is an excellent way to engage with thought leaders shaping the art world. Whether seated beside a major patron of the Whitney or exchanging insights with a gallery owner in Venice, these moments build the kind of social capital that money alone cannot afford.
Where, How, and With Whom Will You Spend the Weekend?
The super rich do not simply spend their weekends—they curate them. Whether collecting classic cars, sailing, or horse racing, these pursuits are indulgent and lots of fun. But do not underestimate their influence. Such hobbies could also be keys to locked doors in your community.
