50 Best Ways to Entertain Yourself When You Are Rich
Money does not buy happiness — but it does buy options. And when the options available to you extend well beyond the ordinary, the question of how to spend your time becomes genuinely interesting. The wealthy have always found ways to fill their hours that go beyond the everyday, from private islands to bespoke experiences that most people will never encounter. This list is a celebration of exactly that — fifty ways to entertain yourself when the budget is not a constraint, ranging from the quietly luxurious to the genuinely extraordinary.
1. Charter a Private Yacht
There is no more complete form of freedom than being at sea with nowhere particular to be. Chartering a private yacht — whether a sleek motor yacht for a weekend in the Mediterranean or a tall ship for a transatlantic crossing — puts the ocean entirely at your disposal. You choose the route, the pace, the ports of call. The crew handles everything else. Days spent this way have a quality of suspended time that is almost impossible to replicate on land, and the combination of movement, water, and genuine remoteness produces a kind of mental clarity that money spent almost any other way rarely achieves.
2. Commission a Work of Art
Art collecting is one of the oldest and most satisfying ways wealthy people have occupied themselves, but commissioning a work takes the experience to another level entirely. Working directly with an artist — discussing the concept, watching the piece develop, seeing your own ideas and aesthetic sensibility translated into something permanent and beautiful — is a deeply personal process. The result is not just an object but a relationship, a collaboration, a piece of your own story made visible. Whether you commission a portrait, an abstract canvas, a sculpture for your garden, or a site-specific installation, the experience of bringing a work of art into existence is one that money makes possible and very few people pursue.
3. Hire a Professional Companion in London
London is one of the world’s great cities, and experiencing it with the right company transforms it entirely. For those visiting the capital or simply looking for exceptional companionship for an evening, CharlotteAction offers some of the finest companion services in London. Their companions are sophisticated, engaging, and genuinely knowledgeable about the city — equally at home at a Michelin-starred dinner in Mayfair, a private members’ club in Soho, or a quiet evening in a beautiful hotel suite. For the wealthy traveller who wants to experience London at its most memorable, engaging a professional companion through a reputable agency like CharlotteAction is an option that delivers returns far beyond its cost. Visit charlotteaction.org to explore what is available.
4. Buy a Table at a Private Members’ Club
The world’s finest private members’ clubs — from Annabel’s in London to Soho House’s global network to the legendary Roppongi Hills Club in Tokyo — offer something that money alone cannot always secure: genuine exclusivity. Membership at the right club is a passport to a social world that operates by its own rules, at its own pace, with a quality of service and a calibre of fellow member that open venues simply cannot match. The best clubs are not just places to eat and drink — they are communities, and the relationships formed within them often become among the most valuable a wealthy person possesses.
5. Take a Helicopter to Dinner
The logistics of getting somewhere have always been a constraint on experience. Remove them, and the possibilities expand considerably. Taking a helicopter to dinner — whether to a remote coastal restaurant accessible only by air, a vineyard in the hills above a city, or simply to avoid the traffic of a busy metropolis — is the kind of casual extravagance that transforms an evening from pleasant to genuinely memorable. The approach by air, the landing, the sense of having arrived somewhere in a way that most people simply don’t — these things add a dimension to an evening that the food alone, however exceptional, rarely provides.
6. Build a Private Cinema
The home cinema has become almost commonplace among the wealthy, but a truly exceptional private cinema is something else entirely. Think a dedicated room designed from the ground up for the best possible viewing experience — acoustically treated walls, a screen that fills your field of vision, seating that makes commercial business class look modest, and a projection and sound system that rivals or exceeds the best commercial venues. Add a programmable lighting system, a bar, and a professional-grade projector, and you have an entertainment space that makes every evening at home feel like a premiere.
7. Attend the World’s Greatest Sporting Events
There is a significant difference between watching a sporting event and experiencing it. The Monaco Grand Prix from a terrace above the Rascasse corner. The Masters at Augusta from the fifteenth fairway. Wimbledon from the Royal Box. The Super Bowl from a premium suite. These experiences require not just money but access — the right connections, the right hospitality partner, the right moment to ask. For those who have both the resources and the relationships, the world’s great sporting events offer a level of spectacle and atmosphere that television, however good it has become, cannot approach.
8. Take a Polar Expedition
The polar regions — Antarctica and the Arctic — remain among the few places on earth that genuinely feel remote, genuinely feel untouched, genuinely feel like somewhere that has nothing to do with the modern world. Expedition cruises to these regions have become the preserve of the serious wealthy traveller, combining genuine exploration with extraordinary wildlife encounters and a scale of landscape that recalibrates your sense of what the world is. Seeing a tabular iceberg the size of a city, or watching a polar bear hunt on the sea ice, or standing at the edge of the Antarctic continent at midnight under a sky that never quite darkens — these are experiences that change how you see everything else.
9. Design and Build Your Dream Home
Few projects are as all-consuming, as creatively satisfying, or as genuinely expressive of who you are as designing and building a home from the ground up. Working with an architect of genuine talent — someone who listens as well as creates — to produce a house that is entirely yours, entirely original, and entirely suited to how you want to live is an experience that occupies years and produces something permanent. The process itself — the drawings, the models, the decisions, the inevitable complications, the slow emergence of the finished thing — is one of the great creative adventures available to those with the resources to pursue it.
10. Create a Wine Cellar Worth Exploring
Wine collecting at the highest level is part investment, part passion, part lifestyle. Building a cellar that contains the great vintages of Bordeaux and Burgundy, the finest bottles from Napa and Tuscany, the rare expressions from emerging regions that most people will never encounter — this is a project that takes years and rewards patience. The cellar itself, if designed well, becomes a destination: a temperature-controlled room lined with bottles that represent history, geography, and the patience of nature distilled into glass. The evenings spent exploring it, with the right people and the right food, are among the most civilised pleasures available to the wealthy.
11. Travel by Private Jet
Commercial aviation, even at its most luxurious, involves compromise. The private jet removes the compromise entirely. You depart when you choose, from whichever airport is most convenient, to whichever destination suits you, with the cabin configured exactly as you prefer and the company limited to people you have actually chosen to be with. The time savings are significant. The reduction in friction — no security queues, no terminals, no waiting — is transformative. But the deepest pleasure of private aviation is simpler than any of this: the sense that the machine is working for you, rather than the other way around.
12. Host a Private Concert
The concert experience — however good the artist, however fine the venue — involves a crowd. Remove the crowd, and something intimate and extraordinary becomes possible. Commissioning a private concert, whether a classical quartet in your drawing room, a jazz trio for a dinner party, or a full band performance for a significant birthday celebration, transforms music from something consumed to something shared. The artists perform differently without the distance of a large venue. The audience listens differently without the distraction of strangers. The evening becomes, in the truest sense, yours.
13. Go on a Safari in a Private Reserve
The great safari destinations of Africa — the Serengeti, the Okavango Delta, the Maasai Mara, the private reserves of the South African bushveld — offer wildlife experiences that have no equivalent anywhere else on earth. At the luxury end, private reserves with exclusive camps mean that your game drives are unshared, your sightings undiluted by the presence of other vehicles, and your experience of the bush genuinely immersive rather than curated. Waking before dawn to the sounds of the African bush, watching a leopard from twenty metres in the golden morning light, eating dinner under a sky of impossible stars — these are experiences that wealthy travellers consistently rate among the most significant of their lives.
14. Collect Rare Watches
Horology at its finest is a form of miniature engineering that borders on art, and collecting serious watches — the great complications from Patek Philippe, the sports references from Rolex’s vintage catalogue, the independent watchmakers producing extraordinary pieces in tiny numbers — is a pursuit that combines aesthetic pleasure, intellectual engagement, and investment potential in roughly equal measure. The community of serious collectors is international, passionate, and deeply knowledgeable, and the conversations that happen around exceptional watches often lead to friendships of unusual depth and quality.
15. Take Cooking Lessons from a Michelin-Starred Chef
The gap between eating well and cooking well is one that most people never cross, and with good reason — learning to cook at the highest level requires time, focus, and access to the right teachers. For the wealthy food enthusiast, private cooking lessons with a chef of genuine distinction offer an experience that is simultaneously humbling and exhilarating. Working in a professional kitchen, understanding the techniques and thinking behind dishes you have admired from the other side of the pass, developing skills that translate directly into your own cooking at home — this is an investment in pleasure that pays dividends for the rest of your life.
16. Sponsor an Archaeological Dig
The wealthy have always been patrons of discovery, and sponsoring an archaeological excavation is one of the more unusual and genuinely exciting ways to exercise that tradition. The right project — in Greece, Egypt, Turkey, Central America, or any of dozens of other locations where the ground still holds significant secrets — offers the possibility of genuine involvement, regular updates from the field, and occasionally the extraordinary experience of being present when something is found. The sense of connection to history that comes from funding its recovery is difficult to replicate through any other form of patronage.
17. Build a World-Class Home Library
Books are among the cheapest pleasures available to anyone, but a serious library — a room designed specifically for the purpose, with floor-to-ceiling shelves, a rolling ladder, a reading chair of exceptional quality, and a collection assembled with genuine taste and purpose — is something that only the wealthy can fully realise. The process of building such a collection, working with specialist booksellers, attending auctions, hunting for specific first editions and presentation copies, is itself a form of entertainment that can occupy years. The room it produces is among the most civilised spaces a house can contain.
18. Take a Masterclass in a Subject That Fascinates You
The wealthy have always had access to the best teachers, and …
