Planning a dream vacation is no easy feat, even for the most seasoned advisors. It takes a village of trusted suppliers, reliable service networks and savvy destination experts who know how to deliver the best experience. But more than that, successful vacations require mutual trust, understanding and clear lines of communication between the client and their advisor.
No matter what kind of travel dreams you’re helping bring to life, check out these accounts from travel advisors about how they pulled off the ultimate trips for their clients.
Delia DuPlessis Books Solo 80th Birthday Trip
Take the story of Dream Destinations Agency owner Delia DuPlessis and her client Sally, who wanted a solo trip to Africa for her 80th birthday. Sally dreamed of close encounters with her favorite wildlife animals, stays at luxury tented camps and safari resorts, meaningful interactions with local villagers and as many thrilling “Out of Africa” moments as possible.
“The resilience of this woman, determined to travel alone for the first time at her age, was inspirational,” DuPlessis said.
Sally’s birthday was only a few short months away when she reached out, but DuPlessis accepted the challenge based on her passion for and experience in planning African safaris.
DuPlessis organized a safari tour of Kenya, Zimbabwe and South Africa, where Sally enjoyed a tented camp stay at Zebra Plains Collection in the Masai Mara Reserve, a visit to Nairobi’s Sheldrick Wildlife Trust to meet giraffes and baby elephants, rejuvenating spa treatments at Thornybush Lodge in South Africa and a private art tour and penguin sightings in Cape Town and Boulder Bay.
Sally even got her wish to see Victoria Falls in Zimbabwe, which she described as “a curtain of diamonds in the sun.”
Not everything was easy, though. Challenges included an in-destination booking mix-up that cost Sally her original Victoria Falls tour choice and not getting the elephant art safari due to miscommunication with the tour guide. Still, DuPlessis was able to pivot and offer similar alternatives. The end result, DuPlessis said, was a satisfied traveler who walked away from her vacation feeling empowered, full of joy and with newfound friends.
Suzanne Haire Maps Tour for Art History Student’s Dissertation
When romance travel specialist Suzanne Haire overheard a college bartender at a local tavern one night mulling over her dissertation topic ahead of her upcoming semester abroad in the U.K., Haire’s ears perked up.
Taylor, an art history graduate student, wanted to see museums and historic sites in Europe and the U.K. — and somehow weave that experience into her dissertation. Haire suggested she visit the continent ahead of the semester to jumpstart ideas. Several planning sessions later, Haire and Taylor came up with a 200-page bound-book itinerary for a six-week trek across the U.K. and Europe, ending in Budapest just before classes began.
Spreadsheets were key, outlining everything from transportation between cities, tours, embassy locations and more, with blank sheets added in between for Taylor to take notes and document important findings for her paper.
Haire maximized her commissions by letting Taylor know upfront the hourly rate she would charge for bookings that didn’t pay commissions and accepted commissions as-is for bookings that did offer them.
There were some hiccups along the way, including Taylor temporarily losing her fanny pack in a taxicab that was later returned intact, money and all — which Haire credits to using a reputable transfer company.
“It may not have been a huge ordeal except all her money was in it,” Haire explained. “So I worked right away to find the shuttle driver who was able to locate her fanny pack and return it to her.”
Gina Porter Plans Celebratory Trip (and Surprise) of a Lifetime
Gina Porter, founder of GG Luxury Travel, is crafting a special trip to Paris next May to mark a couple’s 35th wedding anniversary and the wife’s 60th birthday — and some surprises are already unfolding.
Referred by a previous client, the husband told Porter he wanted this trip to be a testament to their love and the life they’ve built together over the last three decades.
The custom itinerary Porter delivered includes Michelin-starred dining, a private Seine cruise and an exclusive after-hours visit to Versailles. There’s also a special gift: an 80-page hardcover photo album that showcases the details of their upcoming Parisian adventure, complete with family photos and heartfelt birthday wishes from loved ones.
“On her birthday, he presented it tucked inside a new handbag she had always dreamed of,” Porter said. “The moment became as unforgettable as the trip itself.”
Planning the surprise elements was tricky, Porter said, as she had to balance secrecy with the practicalities of booking international travel. But clear communication and strong local supplier relationships have set the trip up for success.
Porter maximized her commissions by charging separate travel design fees and creative fees for producing the 80-page photo book. She also strategically partnered with hotels that offered suites with higher commission rates and provided additional amenities like daily breakfast, complimentary upgrades and VIP transfers.
“I am always transparent about pricing and fees, and in this case, the client was thrilled with the value he received — both from the seamless logistics and from the creativity that transformed the trip into an unforgettable experience,” Porter said.
Shaun Alcott Crafts Special Honeymoon
A newlywed couple that always wanted to visit South Africa and Victoria Falls got the honeymoon of their dreams from Shaun Alcott, a destination specialist at Kensington Tours with more than 20 years of experience planning trips throughout Africa.
Alcott said the key to success for pulling off this trip was qualifying her new clients and learning more about who they were and what they wanted.
“You really want to learn about the client, and what their lifestyle is like and what their expectations would be when they’re coming into their trip,” Alcott said.
The trip began in Cape Town, where the couple toured sites like Table Mountain and enjoyed privately guided tours in the Cape Winelands. Alcott booked them a number of culinary experiences and worked with resort staff to deliver surprise touches, like scattered rose petals, chocolates and freshly drawn bubble baths in their rooms, in addition to spa appointments.
“We have a partner in South Africa who is fantastic; it all comes through teamwork as we all work together on this,” Alcott said.
Surprise upgrades are an added touch Alcott likes to take advantage of, especially since they’re also a great way to earn higher commissions. To achieve that, Alcott stressed the importance of knowing your clients.
“It’s always fruitful when you understand what those clients’ expectations are,” Alcott said, adding that she likes to know how her clients live, whether accommodations or activities are more important to them and what they consider luxury.
Originally appeared in the Winter 2025 issue of The Compass magazine
Nicole Edenedo
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