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You are at:Home » What does the ultimate dream vacation look like? Seamless travel and experiences that defy imagination | Canada Voices
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What does the ultimate dream vacation look like? Seamless travel and experiences that defy imagination | Canada Voices

8 September 20255 Mins Read

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For many high-net-worth individuals, the ultimate luxury is funding all-expenses-paid vacations with friends and family.GETTY IMAGES

We’ve all had that moment: staring out the office window on a dreary Monday, wishing we were anywhere but here. Not a weekend at a friend’s cottage or a visit to the in-laws, but a real escape that feels almost too good to be true.

So what would the ultimate vacation look like if money, time and logistics weren’t barriers to your wildest travel dreams?

Price-is-no-object travellers want amazing trips with no hiccups, says Kemi Wells-Conrad, founder and president of Wells Luxury Travel in Vancouver. After 11 years planning ultra-luxe getaways, she knows that efficiency and ease aren’t just perks – for these travellers, they’re non-negotiable.

“They’re prepared to pay to make sure that everything is as convenient and seamless as it can be,” she says.

For high-net-worth individuals, the red carpet starts with being met at the terminal gate. Private cars, helicopters and jets are standard fare. These travellers also want the best accommodations, more space, private butler service and full personalization. It’s the individualized attention that sets these trips apart, Wells-Conrad says.

The ultimate dream trips aren’t just about five-star service, though, and they often involve exclusive access to places most others simply cannot go. For example, take White Desert Antarctica, a South African ultra-luxury expedition operator that offers overnight week-long stays for around $150,000 CAD per person.

White Desert builds modular fiberglass domes on the ice for guests to stay in, specifically designed to be removable at the end of the Antarctic summer. “There’s something magical about Antarctica, the stillness, the cleanliness. It’s so pure,” Wells-Conrad explains. “It’s special not seeing any other people where you are landing that day.”

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Dream trips may involve exclusive access to places most others simply cannot go, such as Antarctica.GETTY IMAGES

Wells-Conrad recently planned a $1-million, 18-day trip for clients who stayed on Jumeirah Thanda Island, a private island off Tanzania. “They helicoptered into their own tropical island where it was just them and the staff. The island sleeps 10 and costs $42,500 USD [$58,700 CAD] a night.”

Other exclusive access trips include the Vatican Key Master’s Tour, where one guest per day can join the guards to unlock the Sistine Chapel in the morning before the tourists arrive. The privilege costs between $1,500 and $1,800 depending on the time of year.

“I’ve got clients on [the] wait list for next year,” Wells-Conrad says.

Sometimes, the most luxurious experiences happen in places that feel removed from the rest of the world. Cindy Yu, a Vancouver-based travel content creator and founder of food and travel blog The Vancouverite, enjoyed a trip to Great Exuma Island in the Bahamas a few years ago and hasn’t forgotten it since.

“I had never even heard of the Exuma Islands, but it’s evidently a sailing capital of the world, and it has these big regattas,” Yu says. “Shallow turquoise water and white, white sand. You can walk for miles and barely get past waist-deep water.”

The magic was in the Island’s secluded beaches and deserted cays, she adds. “It was so far from civilization and the fact that it’s in North America just made me go, okay, you actually don’t have to go that far.”

Alexandra Grant, a Vancouver-based travel content creator and founder of To Vogue or Bust, says retreats are in hot demand for high-net-worth travellers.

“They want deep travel, they want retreats or they want tours that deepen their experience with the culture,” she says. For example, there are retreats in Tuscany where people can spend multiple weeks learning to cook. One U.S.-based boutique tour operator, The International Kitchen, offers week-long luxury cooking vacations for just under $8,000 per person.

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High-net-worth travellers often want experiential adventures, such as learning to cook in Tuscany over multiple weeks.GETTY IMAGES

“Experiential travel is really where things are trending,” she says, noting that these kinds of vacations are typically much more expensive than regular tips because they include everything a traveller might need to have that perfect, immersive experience.

There’s a huge range of authentic experiences available outside of the typical tourist destinations, Grant adds. Travellers are moving beyond surface-level tourism to meaningful cultural immersion and authentic local experiences. That might mean trekking through the Gobi Desert in Mongolia or learning martial arts from a sensei in Japan.

“People want to come back with something tangible, [like] a real understanding of a culture or history,” Grant says. “They really want that deep travel experience.”

For many people, the ultimate luxury is funding extraordinary, all-expenses-paid vacations with friends and family for celebrations and milestone birthdays, says Wells-Conrad.

She points to yacht buyouts in the Galapagos Islands, where ultra-luxe travellers buy out the entire vessel to enjoy with their loved ones.

“If you get enough people together, you could have your own private chef. The itinerary, the whole deck space is just for you and your friends,” she says. Some companies offer a dedicated naturalist guide who will lead up-close-and-personal tours of the area’s unique flora and fauna.

Wells-Conrad’s most ambitious project as a luxury travel advisor? That would be a 36-day private jet journey to 10 countries including Japan, Australia, United Arab Emirates and France. That astonishing expedition was crafted for a self-made, 44-year-old entrepreneur and his parents, costing upwards of $1.5-million.

“He treated his parents and his parents’ best friends,” she says. “Every night, they got the three top suites in every hotel, the best restaurants in the world, the best spa treatments.”

Wells-Conrad, Grant and Yu agree that this kind of top-tier luxury is exactly what unlimited budgets can buy: the impossible made real and memories that truly are unforgettable.

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