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As May arrives, so too does the true start of the social season. Across the world’s most iconic destinations, invitations are being sent, yachts are polished, and Champagne is chilling in anticipation. Whether it’s a front-row seat at the Met Gala, a private box at the French Open, or a secret garden party in Belgravia, May is when luxury living hits its stride.
From the racing tracks of Monaco to the rose gardens of Chelsea, and from the glittering ballrooms of Florence to the waterfronts of Porto Cervo, the month offers something for every passion — sport, fashion, art, or simply the joy of beautiful places and even better company.
This luxury calendar in May is your definitive guide to the events that matter, the places that count, and how to enjoy it all with impeccable style.
High Society Gatherings
Kentucky Derby
Louisville, Kentucky, USA | 3 May
At Churchill Downs, tradition and extravagance intertwine. Expect mint juleps, hand-crafted hats, and the most exclusive private suites overlooking the finishing line.
In the heart of Louisville, historic hotels like The Brown offer old-world charm paired with modern luxury, while private jets fill the skies as racegoers descend for the weekend’s legendary soirées.
Formula 1 Miami Grand Prix
Miami, Florida, USA | 2–4 May
Miami transforms into a playground of speed, glamour, and superyacht parties. After the racing, the real celebrations happen in the city’s chicest rooftop lounges.
The marina teems with gleaming yachts, while penthouse suites at The Setai and Faena become the backdrop for glittering afterparties — all a quick ride from private planes landing at Opa-Locka Executive.
Royal Windsor Horse Show
Windsor, UK | 15–18 May
In the majestic private grounds of Windsor Castle, this equestrian showcase brings together royalty, showjumpers, and carriage drivers in a setting like no other.
Nearby, storied estates like Cliveden House and Coworth Park offer regal retreats, with many guests arriving directly by helicopter to the green lawns of the countryside.
Badminton Horse Trials
Gloucestershire, UK | 7–11 May
Set against the rolling Cotswold countryside, Badminton is a quintessentially British event where fine country style meets world-class sporting excellence.
Surrounded by postcard-perfect villages, guests tuck into champagne picnics after arriving by helicopter, before retiring to cozy but opulent country manors such as Whatley Manor.
Met Gala and Afterparties
New York City, USA | 5 May
The Met Gala at The Metropolitan Museum of Art is fashion’s crowning moment. This year’s theme, “Superfine: Tailoring Black Style”, promises bold, creative red carpet looks. After the main event, the city’s most prestigious penthouses and hotels host ultra-exclusive afterparties — often more unfiltered and dazzling than the Gala itself.
The Mark, The Carlyle, and Aman New York become secret playgrounds for the elite, who sweep in from Teterboro Airport via blacked-out SUVs and vanish into shimmering towers of Upper East Side luxury.
Cartier Queen’s Cup
Windsor, UK | 20 May
Guards Polo Club hosts one of the season’s most elegant matches, set within the parkland of Windsor Great Park and drawing the British aristocracy, celebrities, and the international elite.
Champagne flows under striped pavilions, with helicopters buzzing in from London and discreet cars ferrying guests to private dining rooms at Coworth Park after the final chukka.
Emirates Poules d’Essai
Paris, France | 11 May
Held at Longchamp Racecourse, Paris’s Emirates Poules d’Essai is France’s version of the 2000 and 1000 Guineas. A must for the thoroughbred racing set, the atmosphere here blends elegance with old-world sporting spirit.
Set in the heart of the Bois de Boulogne, just a stone’s throw from Avenue Montaigne’s couture houses and the gilded salons of The Ritz, the racing blends effortlessly into evenings of haute cuisine and rooftop revelry.
Betfred 2000 & 1000 Guineas Stakes
Newmarket, UK | 3–4 May
Held on the historic Rowley Mile course at Newmarket, the 2000 and 1000 Guineas mark the beginning of the British flat racing season with unmatched pedigree and pageantry. These two Classic races attract the racing elite and impeccably dressed crowds who appreciate tradition at its finest.
Just a short ride from Cambridge, the scene blends elegant race day style with private champagne boxes and intimate post-race dinners in Georgian country manors. Helicopters and chauffeurs whisk guests in from London for a weekend of heritage and high-stakes racing.
Art and Cultural Prestige
Frieze New York
New York City, USA | 7–11 May
Frieze takes over The Shed at Hudson Yards, bringing contemporary art’s biggest names to one of Manhattan’s most exciting new cultural hubs. Expect curated booths, private collector previews, and after-hours gallery receptions across the city.
Helicopters ferry collectors from the Hamptons to penthouses at Hudson Yards, where sleek cocktail bars and private dinners keep the art conversations alive long after sunset.
Major Spring Art Auctions
New York & Hong Kong | Early to Late May
Sotheby’s, Christie’s, and Phillips present modern and contemporary masterpieces — from a $70 million Giacometti sculpture to rare Basquiat works. Private previews are an art world must for serious collectors.
In New York, celebrations spill over into Cipriani’s golden halls, while in Hong Kong, rooftop terraces at the Rosewood offer panoramic views over Victoria Harbour for exclusive bidding afterparties.
Petworth Park Antiques & Fine Art Fair
West Sussex, UK | 16 – 18 May
Against the historic backdrop of Petworth House, this fair offers collectors a chance to acquire rare furniture, jewellery, and fine art in an elegantly understated setting.
The surrounding South Downs National Park invites country strolls between acquisitions, with grand country houses offering butlered service and roaring fires to end the evening.
Art International Zurich
Zurich, Switzerland | 23 – 25 May
Zurich’s Kongresshaus transforms into a global art salon with a distinctive Swiss precision. Expect works from emerging international talents alongside established names, and plenty of opportunities for private viewings and acquisitions.
Art collectors retreat to lakeside sanctuaries like Baur au Lac and The Dolder Grand, where Swiss hospitality meets understated glamour, often arriving straight from Zurich’s private aviation terminal.
Floral and Garden Spectacles
Belgravia in Bloom
London, UK | 19–26 May
Throughout London’s most elegant district, boutiques, galleries, and residences come alive with showstopping floral installations. A gentle, immersive stroll here captures the spirit of a London spring at its most luxurious.
Hidden courtyards, private garden squares, and elegant cafés like Peggy Porschen’s transform the week into an enchanting floral wonderland, just steps from The Lanesborough and The Berkeley’s most sought-after suites.
RHS Chelsea Flower Show
London, UK | 20–24 May
Held at the Royal Hospital Chelsea, this is the pinnacle of the horticultural world, drawing designers, celebrities, and members of the Royal Family. Gala evenings are an insider favourite for the champagne-fuelled, after-dark garden tours.
Nearby, Belgravia’s private residences host glittering garden parties, while Mayfair’s private members’ clubs become the watering holes of the horticultural elite.
Chelsea in Bloom
London, UK | 19–25 May
Running alongside the RHS Chelsea Flower Show, Chelsea in Bloom transforms the upscale boutiques, restaurants, and streets around Sloane Square into an open-air floral gallery. With themed installations, immersive displays, and prizes for the most exquisite designs, it’s a must-see extension of London’s floral fever.
The surrounding area is a playground of quiet luxury, with guests pausing for rosé at The Ivy Chelsea Garden or checking into The Cadogan for an effortlessly elegant stay. Chauffeured cars glide between events as Chelsea comes alive with scent, colour, and couture-level floristry.
Stage, Screen, and Performance
New York City Ballet Spring Gala
New York City, USA | 8 May
Held at Lincoln Center, this glittering evening showcases world premieres, bold choreography, and a guest list blending art, fashion, and philanthropy at the highest level.
Elegant black-tie dinners continue into the night at The Plaza or the Mandarin Oriental, with candlelit terraces overlooking Central Park as the city hums below.
Cannes Film Festival
Cannes, France | 13–24 May
Nothing rivals the spectacle of Cannes. Whether it’s yacht parties moored along La Croisette or late-night premieres at the Palais, Cannes in May is the very definition of cinematic glamour.
The Hôtel du Cap-Eden-Roc and Le Majestic are home base for Hollywood’s brightest, while fleets of helicopters and tender boats buzz between superyachts glittering in the bay.
Glyndebourne Festival
East Sussex, UK | 16 May – 24 August
Synonymous with summer elegance, Glyndebourne offers opera in its most romantic setting — an English country estate surrounded by manicured gardens. From Verdi to Mozart, performances are world-class, but it’s the full-dress picnics on the lawns and the long dinner intervals that define its charm.
Guests don black tie even for matinees, arriving from London by vintage cars or helicopter to dine under the Sussex skies, glass of chilled Chablis in hand, as music drifts across the gardens.
Sporting Elegance
PGA Championship
USA | 15–18 May
The PGA Championship draws the golf world’s greatest players to one of the USA’s iconic courses. Expect tailored hospitality, curated culinary offerings, and discrete VIP viewing experiences.
Players and guests glide in on Gulfstreams to nearby executive airports, with private lodges and fine-dining country clubs offering a restful retreat after the final putt.
Roland Garros – The French Open
Paris, France | 25 May – 8 June
The red clay courts of Stade Roland Garros host one of tennis’s most prestigious tournaments. Paris in late May offers a particularly irresistible blend of sport, style, and sunny afternoons.
The 16th arrondissement pulses with cocktail parties and gallery openings, while Philippe-Chatrier’s courtside seats are the ultimate badge of Grand Slam insider access.
Jet-Set Sailing and Grand Resorts
Regatta at Porto Cervo
Sardinia, Italy | 27 – 31 May
Sardinia’s Yacht Club Costa Smeralda plays host to sleek sailing yachts and glamorous dockside gatherings. From the emerald waters to the exclusive Costa Smeralda resort parties, it’s a gathering point for European high society.
The summer playground of the superyacht set, Porto Cervo, hums with aperitivos at Cala di Volpe and secret afterparties in waterfront villas accessible only by tender.
Monaco Grand Prix
Monte Carlo, Monaco | 23–25 May
Few events capture the spirit of Riviera luxury quite like the Monaco Grand Prix. The winding streets of Monte Carlo create a thrilling backdrop for Formula 1’s most iconic race, with superyachts crowding Port Hercules and terraces overflowing with Champagne and celebrities.
Suites at Hôtel de Paris overlook the action, while private helicopters swoop down from Nice, delivering guests to a weekend of unbridled Riviera hedonism.
Fashion’s Global Summits
Gucci Cruise Collection
Florence, Italy | 15 May
Gucci returns to its Tuscan roots for an extraordinary Cruise Collection runway show set against the backdrop of one of Florence’s historic palazzi. Expect a fusion of heritage, innovation, and global glamour.
Candlelit dinners in hidden Renaissance courtyards and moonlit strolls along the Arno complete the night, with guests slipping away to the grand suites of Villa Cora and Four Seasons Firenze.
Dior Cruise Collection
Rome, Italy | 27 May
Dior’s Cruise showcase unfurls across Rome’s storied landscapes, blending haute couture with la dolce vita spirit.
Historic palazzos glow under the Roman sunset as guests retire to Hotel de Russie or slip into candlelit garden parties behind ivy-draped villa walls.
Vogue Business Global Summit
Lake Como, Italy | 27–28 May
Where fashion’s biggest executives and creative visionaries convene to discuss the future of luxury. Held at a private lakeside villa, this summit is part think tank, part refined networking event.
Classic wooden Riva boats ferry guests across the sparkling water to Villa d’Este, where conversations unfold against a backdrop of silk-draped salons and manicured Italian gardens.
Final Word
May is not simply a month — it’s a celebration of refined living. Whether it’s a private box at Roland Garros, an impromptu yacht party off the Sardinian coast, or a front-row seat at Gucci’s Florence spectacular, each experience is a passport to a world where elegance, culture, and exclusivity rule.
