Writer: Karla Walsh
Flash back to a 1990s mall. Steps from the Gap, Bath & Body Works and the food court, chances are high you’d find a shop or kiosk emblazoned with the words “Travel Agent.” Without access to Google or Yelp, these agents marketed itineraries from catalogs and brochures they received from their agency. The process was straightforward and reliable but also very cookie-cutter.
Even now, when we have overwhelming access to online resources, Whitney Shindelar thinks that using Google or ChatGPT to plan your next trip will give you similar results. Sure, search engines and artificial intelligence allow for more customization and draw from a much wider world of options and reviews, but “they’re missing the human component,” she said. “That means you’re planning with the masses, and you’ll never find those unique, personalized experiences that are tailored to you. Plus, ChatGPT will start making things up if you dig deep enough. How awful would it be to plan an entire day around something that isn’t completely accurate?”
Besides, she added, an AI tool or search engine will give you a checklist of must-sees and -dos, without any consideration of you or your reasons for traveling in the first place.
Enter: the modern-day travel adviser.
Shindelar lived abroad for 10 years, including a five-year stint working at Le Royal Meridien Shanghai in China, where she worked her way up to be the director of operational excellence. She traveled widely, on her own, and sharpened her skills in the hospitality business. She often planned magical experiences for the five-star hotel’s clients but wanted to help other travelers, too.
A few years ago, while she was figuring out the next steps of her career, her parents hired a travel adviser to plan their family trip to Germany. “I was honestly a little miffed. I plan our trips!” she said. “All of the decisions were already made when they presented the itinerary to me. But when I showed up, I was blown away by their attention to detail, the guides and the overall experience.”
After returning to China, Shindelar started paving the way to open her own business in Adel to be closer to her family. “I literally landed back in the States and went to City Hall to start my business, Undiscovered Sunsets,” she said. “My mission: to work more directly with clients to create some of the incredible experiences I’d witnessed in my 10 years abroad.”
I met Shindelar through a mutual friend the same week she landed back in Iowa, and my vacations have never been the same. I originally signed on as a client in 2018 and hired her to plan my first solo trip abroad. This was on my bucket list, but it was something I felt confident to do only with a pro choosing safe places to stay, coordinating drivers and being on call in case any big surprises popped up. I’m happy to report my time in Costa Rica was safe, educational and stress-free — and it changed my life. Traveling abroad on my own gave me the guts to become a full-time freelance writer.
Ever since, Shindelar has been my vacation fairy godmother, introducing me to opportunities I didn’t know existed, like hiking an out-of-the-way path to Machu Picchu, biking through breathtaking Sonoma vineyards and climbing a sky-high via ferrata in the Croatian Alps. Oh, and after that climb? A birthday cake awaited me at the hotel since the staff somehow knew I’d be turning 35 the next day.
That’s just part of my fairy godmother’s magic. “All of the guides and hotels and service providers get a full client profile brief before you arrive, so they know things about you and can welcome you as a friend and make you feel seen,” she said.
The key to unlocking unforgettable experiences starts with rethinking the planning process. Most travelers start with a place and an exact time frame. With Shindelar, she starts with the “why,” the purpose for the trip.
“Before deciding on a destination, let’s talk about the vibe of the trip and the reason you’re traveling,” she said. “Is this your husband’s 50th birthday? The last family trip before a child goes off to college? Maybe it’s just to relax after a busy time?”
Each of her clients completes a survey to explain their purpose for traveling, their personal passions — the things they enjoy most in their everyday life — and their budget. After that, they hop on a call to explain what they loved about previous trips and what they crave in the new one, so she can personalize it and sprinkle in a few doses of enchantment. This requires a bit of trust, but it also paves the way for those life-changing moments.
While some clients do request specific timelines and destinations, Shindelar encourages them to keep an open mind. She’s seen all too many families elbowing through the crowds of Athens in July, fighting for a peek at the Parthenon. Instead, she might recommend visiting in late spring or early fall or heading somewhere else for a summer history lesson.
“The best ‘you might also like’ algorithm is human connection,” she said.
So now, after my initial trip to Costa Rica in 2018, a foodie adventure in Northern Italy in 2023 and some quality time with my mom at a farm resort in Tennessee in 2024, I’m ready for her to send me somewhere new. Care to join?
Three Itineraries
Where will Karla go next?
With my purpose (conquering a new challenge), passion (food, drink, local culture), timeline (10 days) and budget (approximately $10,000), Shindelar suggested three itineraries for this fall. Which one would you choose? And which do you think I’ve chosen?
Option 1: Alaska
Unlike the supersized cruises that carry more than 5,000 guests, Shindelar thought a nature-focused Lindblad Expedition on an intimate 62-passenger ship would reel me in. I’d told her about an overwhelming mega-ship cruise when I was in junior high but said that I was ready to rewrite that narrative. “When seeking out a challenge, I often think about challenging our beliefs about something that we think we don’t like,” she told me. “Not only will an expedition cruise challenge your sentiments on cruising, but it will also show you a side of Alaska that isn’t accessible any other way.” The itinerary includes hiking through forests; sailing past glaciers; spotting wildlife like humpback whales, bears, otters and bald eagles; and learning from local conservationists about how they’re protecting the land and waters that surround our nation’s largest state.
Option 2: Spain
I’ve been to Portugal but have yet to explore its neighbor. After reflecting on my previous travels, Shindelar pointed me toward southern Spain, home to stunning architecture, flamenco, football (aka soccer) and plenty of opportunities for biking, hiking and canyoning. Those al fresco challenges are accessible just outside of prominent cities like Seville, Malaga, Granada and Ronda, so I won’t be spending precious out-of-office time on lengthy commutes. Besides the outdoor adventures, this itinerary includes a cooking class and market visit, an outing that combines flamenco and tapas, a sojourn to the homeland of Iberico pork, and a sunset visit to the iconic Alhambra palace.
Option 3: Japan
“Whereas southern Spain will challenge you physically and an expedition cruise will challenge your beliefs on certain styles of travel, Japan will challenge you mentally,” Shindelar explained. I took four years of Japanese in high school, but I’m beyond rusty, so this destination would definitely be humbling and require courage. Whitney assured me that overcoming my language insecurity would make the trip more than worth it. Temples, gardens, history, culture and nature are all part of the agenda, along with a deep dive into the local food and drink scene in Tokyo and Kyoto.
And the winner is …
All three vacation options are tempting, but the splendor of Spain is calling my name. From the albondigas (meatballs) and Albariño (white wine) to trekking El Caminito del Rey near Malaga (a hike once considered among the most dangerous hikes in the world), I chose this option from Shindelar’s terrific trio. I’ll file away the others for the future.
If you’re curious, follow me on Instagram @karlaswalsh starting Sept. 19, and I’ll take you along on that harrowing hike, into a few five-star hotels, at the table for a few of my favorite meals, and more. Afterward, I’ll recap the trip in an October edition of the dsm Weekly newsletter.
Pack your bags
If you’re feeling inspired to chart new territory, travel adviser Whitney Shindelar suggests contacting her six to 10 months before you’d like to travel. Itineraries include transportation, accommodation, activities and experiences. She’ll ask you about the purpose for your trip and your passion, timeline and budget; then she’ll take it from there. Planning fees typically range from $750 to $1,200 for a one- to two-week trip. Visit undiscoveredsunsets.com to kick things off.
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