Sitting on a beach staring into space just won’t cut it for many of Donna Greenspan’s clients. Owner of Travel Quest, Greenspan said although they’ll take a dose of relaxation while traveling, her clients also want to learn something and come home with new knowledge, not just a nice tan.
Learning-based vacations are growing in popularity across the globe. But don’t let the name fool you. These types of trips aren’t standard classroom-type experiences. Instead, travelers are taking cooking classes with nonnas in Sicily, learning to tie-dye silk in Japan and discovering the history of chocolate in Switzerland. Plus, some people are even up for a “skillcation,” where they learn a new skill from experts, whether that’s picking up tips from a professional golf instructor or working a cattle roundup on a dude ranch.
“Everywhere you go, there’s something to learn,” Greenspan said. “Don’t just go and sit on a beach. Try something new.”
Understanding Your Client’s Skill-Building Desire
Fueled by her own passion for learning, Greenspan likes to offer an educational experience to her clients, even those who may not have tried traveling in this way before. She recommended thinking carefully about the client and what might appeal to them, even if they’re not typically the most adventurous person. She uses a series of questions to determine the travelers’ tolerance:
- How much of an adventure are they open to? What about their travel partners?
- How much moving around are they comfortable with?
- What have they enjoyed before?
- What might they be willing to experience for the first time?
Once she understands the traveler, she’ll entice them with some creative planning.
For example, when booking a trip for grandparents taking their granddaughter to Sicily, she suggested a pasta-making class that she thought would appeal to the group. For another family staying in Lake Como, she enticed the adults to take a trip over the border into Switzerland for a chocolate factory tour she thought the kids would love.
For an adventurous group of couples heading to Greece, Greenspan expected that an olive oil making class in Crete would be a hit — and she pushed their comfort zone a bit by booking a historical tour of an area that used to be home to those with leprosy.
For a tour with a group of women, she booked them into Gelato University, where “graduation” came with sweet samples, of course.
“The women who were a part of that still talk about the ‘Professore of Gelato’ because it was so unique,” Greenspan said. “I like to always offer the client something interesting, and hopefully they take it and run with it.”
Greenspan often draws upon history and food as inspiration to guide her educational recommendations, whether that’s an exploration of the jewelry of the Medicis, a deep dive into the construction of the Ponte Vecchio or a whiskey tasting paired with a history on Scottish songs.
Sourcing Learning-Based Experiences
Advisors newer to booking educational experiences can start by asking tour operators for suggestions, then grow to more one-of-a-kind opportunities as they become more comfortable.
Greenspan relies on relationships with guides she’s met over the years to help her find off-the-beaten-path experiences. Cultivating that cooperation with on-the-ground local experts is key to discovering unique offerings for guests.
However, she noted that means larger, preferred suppliers don’t always have what she's looking for, and that can spell little to no commission. For her, making the client happy is more important than the money, and she knows she can make commission on other parts of the trip.
While the educational experience is important, Greenspan doesn’t sacrifice on the other important aspects, such as a comfortable hotel stay, a spa treatment or time to relax on the beach. There’s time for it all.
Planning a “Skillcation,” Dude-Ranch Style
For some travelers, a cultural experience isn’t enough. Instead, they’re looking to truly immerse themselves in a different life. They want to bring home not just new knowledge, but new skills they can put into practice. That’s where a “skillcation” comes in.
One of the most off-the-beaten path skillcations that’s growing in popularity is True Ranch Collection’s dude ranches, which include horseback riding, square dancing and mountain vistas in Arizona, Montana and Wyoming. The dude ranches promise an escape from the typical modern American life, along with a chance to learn new skills. Guests can help care for the herd, work a cattle roundup, practice rodeo skills and sharpen their shooting and archery techniques. After sunset, square dancing and card playing help guests unwind.
It’s a different way of life for guests, many of whom live in stressful suburban or urban lifestyles, according to Russell True, managing partner of True Ranch Collection.
“If you live in a big city, you’ve kind of got to elbow your way through life,” True said. “You get to the dude ranch, and you can put your elbows away. We see people just become relaxed and part of the experience.”
Some people come in with a specific set of skills they want to learn, while others immerse themselves in the experience, open to learning whatever they can along the way.
He hopes that, in addition to learning a new way of life, guests leave with a better understanding of the historical significance of the dude ranch in the American West.
True knows that most people who experience True Ranch Collection aren’t going to give up their lives and become ranch hands. But the skills learned at the dude ranch live on inside of them, whether it’s a little kid learning to ride a big horse or an adult going on a fast trail ride.
“Maybe they don’t ride again, but they conquered a fear and achieved something, and that has lifetime value,” he said.
Greenspan said no matter if a client is saddling up in Arizona, cooking at a grandma’s house in Italy or learning about the art of Japanese textiles, offering them a little education with their fun can take a trip from great to unforgettable.
“When you get somebody who wraps their head around it and is willing to jump with both feet, it makes the trip so much more wonderful,” said Greenspan.
5 Skill-Building Vacations To Watch for Right Now
- Dude Ranches: With locations in Arizona, Montana and Wyoming, True Ranch Collection offers horseback riding for all ages, starting at age five. Other experiences include cattle drives, grooming horses and archery courses.
- Kids’ Golf Experience: Adults may be used to the typical golf trip, but this skillcation offers little ones a chance to discover the fundamentals of the sport. Velas Vallarta, a family-friendly, all-inclusive in Puerto Vallarta, Mexico, pairs kids ages six to 15 with professional golf instructors for personalized golf instruction.
- Surf Camp: Surf camp may conjure images of Hawaii, and the Aloha State certainly delivers with a variety of surf schools, but interested travelers can learn to ride the waves everywhere from Costa Rica and Morocco to New York City.
- Rock Climbing: For those who want to do more than practice on the climbing wall at the local gym, White Stallion Ranch in Arizona offers beginner, intermediate and advanced routes on boulders and rock faces with an instructor leading the way.
- Culinary Experiences: From cooking with a nonna in Sicily to exploring the cheese-making process in Parma, Italy is packed with culinary adventures. Sites like GetYourGuide and Airbnb Experiences are a good place to start.
Orginally appeared in the Fall 2026 issue of The Compass magazine
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