Outrageous proposals and superyachts: How the rich travel for love

Garrett Gardner


When you’re a finance tycoon, oil baron or heir to the family fortune, the standard romantic gesture won’t do. The ultrarich require ultra-opulent tokens of affection.

Enter the ultraluxury romantic vacation.

These lavish adventures celebrate love and lust at obscene costs, from million-dollar proposals to six-figure anniversary trips.

The formula is often simple: Just take a universally beloved travel experience (a trip to Rome, an African safari, a sunset cruise) and inject it with hundreds of thousands of dollars to get a version fit for the 1 percent (the Vatican to yourself, a private island off Madagascar, a superyacht for two).

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“It’s this mix of access to the inaccessible and luxury at its finest,” said Barnabas Carrega, co-founder and CEO for GR8 Group, a “global experience agency” that caters to mega-wealthy clientele.

Just how inaccessible and luxurious? Well, for starters, Carrega’s company recently shut down the Palace of Versailles to arrange a private dinner for a couple celebrating their 10-year anniversary. That’s just the beginning. In honor of Valentine’s Day, here’s a taste of how the world’s richest people travel in the name of love.

A yellow diamond in a clam shell off Madagascar

For the son of one of her wealthiest clients, Julia Carter, founder of Craft Travel, pulled out all the stops to coordinate an over-the-top proposal to his longtime girlfriend on their trip to Africa. They started with an ultra-luxe safari in Botswana, then flew private to Madagascar (just under $100,000 round trip) where they caught a helicopter ($3,200 round trip) to Miavana, a private island home to 100 species of lemurs where villas run $7,000 per night for two guests.

Carter arranged a diving excursion for the scuba-enthusiast couple, after which they returned to their private boat. There, the client asked his girlfriend to open a clam he’d “found” during their swim. Inside was a Graff yellow diamond ring. The girlfriend said yes, and the couple toasted the occasion with vintage Ruinart Champagne bottled the year the bride-to-be was born. They’re now considering renting out the entire Miavana property for their wedding, which would cost about $100,000 a night.

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A custom play performed on a private jet

When you can afford to buy anything on the planet, next comes “the desire for something that is not available on the mass market,” said Matteo Atti, chief marketing officer for the private jet company VistaJet and a luxury business development professor at the International University of Monaco. “It’s showcasing love by showcasing how much effort you put into making things happen,” he continued, “not just about buying something off the shelf.”

One such demonstration of this ethos was the client who requested a custom play to be written for his wife — and performed onboard their private jet. “His wife loves theater and he said, ‘I’ll commission a piece,’” Atti said. “We found a group that can perform in small spaces … and they designed and created a piece just for her that only the two of them ever saw.”

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$25,000 worth of fireworks for a superyacht birthday

In his 30 years in the yacht industry, one romantic trip stands out the most for Carl Sputh, ​a charter broker for Northrop and Johnson and former yacht captain (think the “Triangle of Sadness” type). While captain of the Starfire, a 178-foot superyacht, Sputh helped a client arrange a 50th birthday surprise for his wife during their trip around the Los Roques archipelago off Venezuela. “When I say it was in the middle of nowhere, I mean really in the middle of nowhere,” Sputh recalled.

The crew covertly put together a dinner on the beach of a private island, bringing in fireworks and a pyrotechnician by seaplane, transporting furniture, food and decorations to the beach by barge at night. They pulled off the surprise, which included 25 minutes worth of fireworks (about $1,000 a minute). Between the $280,000 for a week on the yacht, $75,000 for the beach dinner, plus $80,000 for general expenses, the birthday trip totaled near a half a million dollars.

Proposing midair during a skydive over Mount Everest

Why get down on one knee when you can propose while skydiving more than 5,000 feet over Mount Everest? For roughly $80,000, the luxury Asia travel company Remote Lands arranged one such proposal, followed by a Champagne breakfast at 13,000 feet.

“It’s the highest mountain in the world, there’s nothing more amazing,” said Catherine Heald, the company’s co-founder and CEO. In addition to the death-defying jump, the American couple — already seasoned skydivers, thank God — also spent three days trekking in Nepal, and time at one of Kathmandu’s most luxurious hotels, Dwarika’s.

An elopement in the Serengeti

With a limitless budget and a week to plan, Hillel Spinner, luxury travel adviser at Embark Beyond, was tasked with finding a “unique and romantic” destination for an ultra-high-net-worth client to elope. They decided on Tanzania, renting out several One Nature Nyaruswiga luxury safari lodges in the heart of the Serengeti for the couple and their two young kids.

They hired a local Maasai leader to officiate the ceremony and 20 Maasai dancers to perform after. The kids were then flown home, and the newlyweds continued to Santorini, Greece, for a week, where they fell in love. Spinner says the couple was thrilled with the trip, which totaled well over six figures.

Truffle hunting in Tuscany for a buried engagement ring

As the co-founder of Roman & Erica, a “lifestyle management company” for the ultrawealthy (annual membership dues start at $100,000), Erica Jackowitz is used to catering to a client’s every whim. Recently, she was given carte blanche to plan a proposal for a client during his upcoming trip to Italy.

She booked them a three-day, roughly $50,000 trip to Florence with a stay at a suite at the Four Seasons Hotel Firenze. Jackowitz worked with a team of stylists to plan outfits that matched each moment of the itinerary. The trip culminated with a helicopter ride to Val d’Orcia in southern Tuscany where the couple went truffle hunting at a private estate in the town of San Giovanni. The day trip was complicated: permits to land in the valley — a UNESCO Heritage Site — were “outrageously expensive,” plus Jackowitz arranged for the ring to be buried and discovered by a truffle-hunting dog. The client said yes.

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A 10-year anniversary (and proposal) expedition to Antarctica

To fulfill a bucket list dream for the girlfriend of a client, Scott Dunn travel curator Rachael Mendizabal arranged a trip to South America and Antarctica. The adventure — which cost between $250,000 and $300,000 — began in the Atacama Desert in northern Chile, where they hiked, cycled, wine-tasted and even stargazed with a renowned astronomer.

The journey continued with a flight to Antarctica’s King George Island, where they boarded a luxury expedition yacht equipped with its own helicopter and submarine. They explored with the late mountaineer and author Edward Webster — which was documented by polar photographer Paul Nicklen and a private film crew. On the couple’s 10-year anniversary, they helicoptered to the emperor penguin colony on Snow Hill Island, then to a tubular icebergwhere the client finally proposed. She said yes, and they toasted with a bottle of vintage Champagne from the year they first met.

The Louvre to themselves for a proposal

After years of his girlfriend dropping hints that Paris was her favorite city, a client came to Adrijana Basic at Kensington Tours to help him plan a proposal trip. Because the girlfriend was an artist, Basic privatized the Louvre for the occasion. Securing the museum requires a “donation” of at least 30,000 euros.

Following the Parisian portion of the trip, the couple flew by private jet to the French Riviera to stay at the Hotel du Cap-Eden-Roc’s Villa Eleana, which costs about $14,000 per night. The trip ended with a cruise around the Cote d’Azur aboard the Lionshare, a 130-foot luxury yacht.

A nearly $1 million ‘White Lotus’ trip for a double anniversary

For a pair of couples both celebrating their anniversary, GR8 Group recently arranged a three-week trip through Sardinia, Greece and Sicily on a 180-foot megayacht. While the excursion came with a nearly $1 million price tag, it blended a mix of high-end and local experiences.

For example, they shut down Sicily’s ancient Greek Theatre of Taormina so the couples could have a private dinner and opera performance. Another day, they learned to make bread with a family who’s been in business more than 100 years.

“Because at the end,” Carrega said, “we don’t want someone to walk away and say, ‘Oh, I spent a bunch of money for all these luxurious services, but was it really enriching for me?’”

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