Before You Book St. Barths… Read This: Inside This Year’s Billionaire Holiday Wish List
From a $19.8M Upperville haven and a month at The Ritz Paris to Tuscan truffles, a $49M Bahamian beachfront escape, and a 2025 Rolls‑Royce Cullinan, this is a playful wish list.
The “Inside This Year’s Billionaire Holiday List” reads like Santa traded his sleigh for a Gulfstream and his North Pole workshop for a global property portfolio. This is fantasy shopping at its finest: part vision board, part passport, all champagne.
Upperville: Love at First Listing
Every great wish list starts at home, and this year’s crown jewel is a $19.8 million Upperville estate that barely had time to hang a wreath before it went under contract in a week. This is not a house; this is a statement. Picture long stone drive, historic Virginia horse country, and the kind of mature trees that have silently watched more history than most museums. The kind of place where the Christmas tree doesn’t just go in the living room—it has its own room.
You can almost hear the crunch of gravel as guests arrive in black SUVs, greeted by twinkling lights wrapped around ancient oaks, lanterns lining the walk, and the soft glow of candles in every window. In the kitchen, copper pots hang over a marble island as someone opens a very serious bottle of Bordeaux, and out back, pastures roll away like a green cashmere blanket. Somewhere a horse snorts in the cold, and you remember: this is what it looks like when “farmhouse chic” actually has a farm.
Christmas at The Ritz, Paris
When Virginia feels too local, the next stop on the wish list is Paris—specifically, The Ritz. Not just a room, of course; that would never do. This is a month ensconced in a suite where the drapes are heavier than your winter coat and the bathroom lighting could launch a second career as a movie star. December in Paris means glittering lights along the Place Vendôme, the smell of butter and sugar drifting out of patisseries, and the quiet, smug knowledge that you can wander back “home” through the same doors Coco Chanel once used.
Here, the holidays are not rushed; they are curated. Breakfast appears as if by magic: silver domes, still-warm croissants, and coffee that could probably negotiate a better interest rate. Afternoons mean shopping for just-one-more-scarf on Rue Saint-Honoré, followed by an apéritif at the bar, where the martini is cold, the napkin is monogrammed, and you suddenly understand why no one in this building ever seems to be in a hurry.
A Private Chef for the Season
Of course, even the best address needs the right company, and on this list, that means a private chef for the month. Not just “someone who cooks,” but a culinary co-conspirator. The kind of chef who looks at your refrigerator, your pantry, and your friends’ dietary restrictions and smiles like it’s a creative challenge, not a problem.
Imagine holiday evenings where no one is anxiously checking the oven or pretending not to worry about the turkey. Instead:
One night is caviar, champagne, and perfect blinis before a formal candlelit dinner.
Another is “pajamas and truffle grilled cheese” by the fire, because luxury is as much about comfort as it is about crystal.
Christmas Eve becomes a procession of family recipes you don’t have to execute yourself—every childhood flavor, none of the cleanup.
The greatest luxury here isn’t the foie gras or the handmade pasta; it’s the time you get back. Time to linger at the table, time to actually talk to your guests, time to enjoy your own home as if you were the guest of honor.
Tuscan Dreams: Biella, Truffles, and Christmas Pasta
From Paris, the wish list drifts south to Italy, where an estate in the hills near Biella or across Tuscany becomes the December chapter you tell stories about for years. Think stone farmhouse turned villa, terracotta tiles, fireplaces so wide you could sit in them, and a long farmhouse table begging for a long, loud lunch.
The fantasy schedule writes itself:
Morning: a walk through misty hills, stopping for espresso that somehow tastes better just because you’re in Italy.
Midday: truffle hunting with a local guide and an overachieving dog, followed by a lunch where those same truffles are shaved—lavishly—over soft scrambled eggs or fresh tagliatelle.
Evening: Christmas pasta. Not the quick weeknight version, but the kind that takes all afternoon, with slow-cooked ragù, stories, and a glass of Barolo always within reach.
Here, Christmas isn’t about a pile of gifts as much as a sense of place: the smell of woodsmoke, the weight of a wool blanket, the satisfaction of a long meal that ends only when someone finally laughs, “Basta,” and pushes the plate away.
Bahamas: 5 Oceans of Holiday- $49 Million
Of course, not everyone dreams in snow and fireplaces. For those whose ideal Christmas color palette is turquoise and white, the wish list includes 5 Oceans in the Bahamas—an oceanfront estate with a price tag flirting with $49 million and a view that casually erases stress.
Here, the holiday lights are the reflection of the sunset on the water, and the tree might be a slender, elegant number in the great room while palm trees sway outside. You trade wool coats for linen and stockings for bare feet on cool stone floors. Days slip by:
Morning swims in a pool that seems to dissolve into the ocean beyond.
Long, lazy lunches in the shade of a covered terrace, sea breeze doing the heavy lifting in the ambience department.
Evenings in an outdoor lounge, where the soundtrack is waves and laughter, not car horns.
It is the opposite of hectic. A place where everything is designed so you don’t have to think about anything at all—except whether sunset is better from the pool, the beach, or the balcony.
2025 Rolls-Royce Cullinan: The Sleigh Upgrade
Santa may have reindeer, but this list has a 2025 Rolls-Royce Cullinan, and that feels like a fair trade. This isn’t just a car; it’s a rolling living room with better stitching. The perfect companion for every setting on this list:
In Upperville, it glides up a frost-kissed drive, the sound of gravel politely muted.
In Paris, it waits outside the Ritz like it owns a piece of the sidewalk.
In Tuscany, it hums through winding country roads, unbothered by distance or time.
In the Bahamas, it pulls up to a private jet or marina as seamlessly as to a front door.
Inside, the Cullinan is all hush and understatement: starlight headliner overhead, impossibly soft leather, and that floating feeling that makes even a grocery run feel like an arrival. It is the one constant in a holiday season spent moving between worlds.
The Real Gift
The true magic of this “Ultimate Luxury Real Estate Christmas Holiday Wish List” isn’t just the properties, the hotel, the chef, the islands, or the Rolls-Royce. It’s the through-line: time, atmosphere, and intention. Spaces that let you exhale. Experiences that feel tailor-made. A season where every setting—whether stone manor, Parisian suite, Tuscan estate, Bahamian beachfront, or the back seat of a Cullinan—whispers the same message: this is your life, not just your vacation.
And if, for now, some of this lives in the realm of playful fantasy, that’s perfectly fine. Every great acquisition, every big move, every bold purchase starts in the same place: an audacious wish list and the willingness to say, “Why not me”?
As always, if any of these homes, destinations, or experiences spark an idea for you, I’m only a call away. Through my global real estate partners, I can quietly open the right doors and manage every detail for you. My Personal Cell is 202-607-4000.
