For billionaires who have seen the world and own homes on multiple continents, the definition of the “best” vacation spot goes beyond scenic beauty. It must combine privacy, exclusivity, have great experiences, and the kind of luxuries money can buy but few can access.
From private islands in the Caribbean to alpine retreats in the Swiss Alps, these incredible destinations I have been to with my Billionaire Boyfriend offer unmatched experiences for those with abundant means and a billionaire’s tastes.
1. St. Barts, Caribbean – Sun, Sea, and Seclusion
St. Barts (Saint Barthélemy) is a compact Caribbean jewel that has become the quintessential getaway for the ultra-rich. Its combination of French flair, white sand beaches, and discreet luxury has long made it the playground of celebrities and billionaires.
Be sure to Charter a Superyacht Around Île Fourchue. We stepped off my Billionaire Boyfriend’s private jet and onto a sleek superyacht for a circumnavigation of the island chain. We anchored in crystal-blue coves. We dove into pristine waters. Plus, we enjoyed champagne sunsets with zero crowds.
Check Out the Fine Dining at Exclusive Beachfront Restaurants. St. Barts hosts an array of gourmet restaurants where Michelin-level chefs craft tasty menus using fresh Caribbean produce. Private beachside tables and sommelier-curated wine pairings ensure an unforgettable dining experience.
One of our favorites was La Cabane at the Cheval Blanc Hôtel. The staff was exceptional and the food the best.
My billionaire boyfriend and his friends told me they like St. Barts because privacy and exclusivity are built into the island’s DNA. From its luxury villas hidden on high promontories to its quiet coves only reachable by private boat, St. Barts checks all the billionaire boxes required of an exceptional vacation spot.
2. Aspen, Colorado – A Winter Wonderland with First-Class Flair
Aspen embodies the modern winter luxury experience: towering Rockies, pristine slopes, and a vibrant, engaging ski scene that rivals its natural beauty. It is the resort of choice for those who want both athletic challenge and refined indulgence.
We hired a Private Ski Guide to Enjoy Untracked Snowfields. Our expert guide and his snowcat gave us access to untouched terrain beyond the public lifts. Think fresh powder all to ourselves and the glow of high-altitude adventure without waiting in lines.
We also hired a drone video service to record us from above the slope. If you have ever imagined seeing yourself skiing through fresh powder like some movie scene, this is a must-have addition.
Aspen’s social season includes invite-only charity balls, art exhibitions, and celebrity-studded fundraisers, allowing guests to ski by day and socialize in priceless elegance by night.
My Billionaire Boyfriend Rates Aspen a 10/10. He loves the world-class skiing with its undercurrent of exclusivity. We booked an exquisite private chalet with its own helicopter pad (although we left the helicopter at home). It even had personal concierge services.
3. The Maldives – Overwater Luxury on the Indian Ocean
For an ultimate tropical escape, few places rival the Maldives. This country of more than a thousand coral islands boasts some of the world’s most private over-the-water resorts. One of my Billionaire Boyfriend’s friends told me it’s “great for billionaires seeking peace and extraordinary marine beauty”.
We Loved Private Atoll Hopping by Seaplane. There’s nothing like gliding above aquamarine seas to private atolls that host just a handful of villas. We landed on our own stretch of beach, snorkeled with mantas, and unwound in an infinity pool overlooking the ocean.
You Can’t Beat Underwater Dining and Marine Encounters. The Ithaa Undersea Restaurant on Rangali was our favorite. It seemed like we were 10 or 15 feet below the ocean level with stingrays, sharks, and all kinds of unique fish swimming next to the walls. The Légine fillet with saffron champagne risotto was amazing.
We had left our cell phones in our bungalow. I had to look up what a “Légine” was and it’s “the French culinary name for toothfish”. Who would’ve thunk it?
We also took a personalized submarine tour of one of the amazing coral reefs. I was nervous about being in a “can” surrounded by water. Drowning has always been one of my biggest fears. But, our pilot, Masveriyaa, spoke enough soothing English to put me at ease.
Isolation and customization reign supreme in the Maldives and those are magical words for billionaires. My Billionaire Boyfriend enjoyed relaxing spa treatments with ocean views and a villa where we stayed with a private slide into the lagoon. I enjoyed that too! Every part of a trip to the Maldives can be tailored to your billionaire’s desires.
See also: https://sablemerricktoo.com/7-best-conversation-starters-for-a-first-date-with-a-billionaire/
4. Lake Como, Italy – Timeless Elegance Amid an Alpine Lakeshore
Lake Como has enticed royalty, artists, and tycoons for centuries with its sweeping lake views, grand villas, and charming villages. This storied Italian retreat offers a sophisticated blend of gentle landscape and high-end culture.
We Cruised the Lake in a Vintage Riva Boat. There is nothing like gliding across the water in style aboard a classic mahogany Riva Boat. Ours was faster than I thought it would be. We stopped at lakeside villas, cafes, and even a secluded beach for a surprise picnic my Billionaire Boyfriend had planned. We concluded the afternoon with some… ahem, naked swimming breaks.
We Took a Private Wine Tour Through Lombardy’s Vineyards. We didn’t drink much wine in Montana. Still, my Billionaire Boyfriend has worked to change my tastes. The region around Lake Como produces exquisite wines. We enjoyed private tastings, vineyard tours, and cellar dinners with master sommeliers guiding the experience.
After living the fast-paced New York lifestyle, Lake Como balances peaceful, slow-paced beauty with access to exquisite Italian food, shopping, and history. My Billionaire Boyfriend called it “an IV for his soul”. Plus, you can’t beat a backdrop worthy of a Renaissance painting.
5. Queenstown, New Zealand – Adventure Capitol Meets Luxury
For the billionaire who doesn’t just want to relax but to do, (that’s my Billionaire Boyfriend) Queenstown, New Zealand, is a playground where nature and high performance come together. Set against the dramatic Southern Alps and beside Lake Wakatipu, Queenstown delivers adrenaline by the bucketload. Plus, it offers sophisticated lodges and private experiences.
You Have to Try Heli-Skiing in New Zealand. We took a helicopter deep into the mountains for untouched snow. But what sets New Zealand apart are the amazing views. We even landed on a remote glacier for a snow camp and a gourmet alpine picnic.
Our Ultra-Exclusive Lodge Included Tailored Itineraries. The staff curated our days around our interests. While I hated to do something without my Billionaire Boyfriend, I took a private vineyard tour while he enjoyed a fishing expedition on a secluded river.
In New Zealand, adventure doesn’t mean roughing it. Every journey is led by professionals with upscale touches. You have private chefs, tailored guides, and logistical perfection. That’s just what Billionaires look for on a trip.
6. Dubai, UAE – Futuristic Splendor and Desert Glamour
Dubai is an urban vision of the future built in the desert, where billionaire visitors can experience an exhilarating mix of luxury shopping, cutting-edge architecture, and cultural splendor.
My Billionaire Boyfriend and I were more interested in the luxury shopping than the cultural splendor. I don’t know how much we spent or how much it cost to ship home, but it had to be A LOT!
Indulge Yourself with a VIP Desert Safari and Dune-Bashing. We took a private fleet of 4×4 vehicles with expert drivers across the sweeping sands for an exhilarating ride. That was followed by a luxury desert camp with fine dining and stargazing. You cannot imagine the number of stars you can see in the desert far from city lights.
Get VIP Access to the World’s Tallest Building. We enjoyed views from the world’s tallest building, the Burj Khalifa, with VIP access to observation decks. Plus, there was nothing like enjoying a multi-course meal atop the city with a private table and panoramic vistas.
My Billionaire Boyfriend says what he loves about Dubai is the scale and grandeur. From Rolls-Royce-lined valet lanes to private helicopter tours of the Palm Jumeirah, the city exudes being exceptional.
7. French Polynesia – Bora Bora and Beyond
French Polynesia offers wide blue skies, volcanic peaks, coral atolls, and some of the planet’s most stunning seascapes. If your billionaire seeks natural beauty paired with top-tier service and ultimate peacefulness, he will love French Polynesia.
We Took Private Lagoon Tours by Luxury Catamaran. We were able to explore hidden beaches, coral gardens, and remote motus (tiny islets) on our catamaran trip. Snorkeling in unexplored waters was amazing. Our exceptional chef prepared made-to-order picnics comprised of local dishes.
Our Overwater Bungalow was Both Functional and Unique. The bungalows came complete with glass-floor panels for watching the sea life. We especially enjoyed sunset dinners put together by private chefs on our personal deck.
French Polynesia turns the raw beauty of the South Pacific into a personal sanctuary. It’s remote, exclusive, and intimate. That makes it the perfect canvas for billionaires to rest, reflect, or pursue romance.
What unites these seven destinations is not just luxury, but endless possibilities. Every location offers experiences that can be tailored, whether your billionaire wants solitude, adventure, culture, party, or peace.
True luxury travel for billionaires isn’t just about having a private jet. It’s about crafting journeys where every moment feels curated, every sight feels exclusive, and every experience feels singular. These destinations embody those ideals. Each offers a unique flavor of the world’s best that life has to offer and will be sure to scratch your Billionaire’s vacation itch.
