Travelers on a Hawaiian vacation often stay at one resort on one island, where they settle in for a week of relaxation. For travel advisor Brittany Placek, understanding Hawaii and what it offers clients required a much longer stay, multiple hotel visits and plenty of time exploring several islands.
This spring, Placek turned her first-ever visit to Hawaii into a 17-day research trip that included four islands, 46 property visits, seven hotel stays, myriad excursions and many hours behind the wheel of a rental car. Placek, who owns Those Who Wander Travel, says that by the time the trip was over, she had gained the expertise she was looking for.
Here’s why she took the trip, and what she learned.
A Strategic Plan
Each year, Placek looks at her bookings and evaluates which destinations are generating the most inquiries. Then, she weighs that data against the amount of firsthand knowledge she has about those places. While her business has historically been buoyed by all-inclusive vacations, recent trends include an uptick in interest in Europe trips and “adventure-style” vacations to destinations such as Alaska and Hawaii. Clients seeking adventure are asking for immersive experiences rather than resort-only vacations, she says.
Recently, Hawaii bookings surged enough to convince Placek that it was time to invest in gathering deeper expertise on the destination. So, she committed to a Hawaii visit and aimed to be there as long as needed to learn and bolster her business.
Placek visited four different islands.
Credit: 2026 Brittany Placek“If I’m going all that way from the Midwest, I’m going to see as much as I can,” she said.
The Planning Process
Placek says that she planned her own trip the same way she plans client trips — she started with foundational components, such as hotels she would overnight in, then plugged in flights, excursions and additional properties where she would do site inspections. She selected hotels based on the types of properties she anticipates booking most often for clients, while also ensuring she experienced properties in a range of price points. She also planned to see accommodations in locations across each island. Her trip took her to the Big Island, Kauai, Oahu and Maui.
On Kauai, for example, Placek stayed on both the North Shore and South Shore to better understand different and oft-visited parts of the island. On Maui, she split time between the communities of Hana and Kaanapali. On Oahu, she stayed at Aulani, A Disney Resort & Spa in Ko Olina, and at a property in Waikiki.
To coordinate the ambitious itinerary, Placek personally emailed every resort she planned to visit to arrange site inspections. Some properties hosted her for meals during her visits.
Her daytime hours were planned around driving routes, appointment times and excursions. Most of the excursions she chose came from recommendations by Iris Jarnesky at The Hawaii Concierge, who pointed her toward both the islands’ must-see experiences and additional activities travelers shouldn’t miss. And many days were packed with stops. On one particular day, a morning property inspection was followed by a helicopter tour, a drive across the island and multiple resort visits. Sometimes she stopped at a resort even if she didn’t have an inspection scheduled so that she could gather content and preview the option for her clients.
A helicopter tour was just one of the many experiences the advisor enjoyed during the trip.
Credit: 2026 Brittany Placek“Even without seeing a room, you can still get a feel for the property,” she said.
Beyond Property Tours
While property tours were the primary objective of Placek's trip, some of her most valuable discoveries happened beyond set appointments. Hotel representatives and locals pointed her toward favorite coffee shops and neighborhood gems — valuable insider knowledge that built her confidence as an advisor.
She also found that supporting locally owned businesses became one of the trip’s unexpected highlights. Whether stopping at a neighborhood cafe or joining an adventure tour, she appreciated getting to know the people behind those businesses, and says she’s excited to direct her clients toward experiences she’s tried herself.
“Now I can tell my clients, ‘You have to stop here and get this,’” she said.
Placek visited 46 properties and stayed at seven hotels.
Credit: 2026 Brittany PlacekAnother part of the trip that pleased Placek was the people she met and the way they welcomed her.
“It felt like the islands gave me a hug,” Placek said. “Everyone was so incredibly kind to me.”
She describes Hawaii as one of the few destinations where the feeling of the place is just as important as the scenery itself.
“That’s something I couldn’t have told my clients before,” she said. “Hawaii is a place you have to experience. It’s the feeling [you get while there] that makes it special.”
The Return on Investment
Placek says that her trip began to pay off almost immediately. She posted content on social media while she explored the islands, and related inquiries came in from those posts. Some converted to bookings, while others prompted her to review previously planned client itineraries and make adjustments based on her new knowledge.
But beyond the immediate business impact, Placek says the expertise she gained made the effort, personal investment and time she put into the trip worthwhile.
“The knowledge I have now is priceless,” she said.
Another important takeaway from her adventure is that she feels far more confident in matching travelers with the right island and resort. She also has standout properties to recommend, including Mauna Lani and The Westin Hapuna Beach Resort on the Big Island; 1 Hotel Hanalei Bay and Koloa Landing Resort on Kauai; Moana Surfrider and Aulani, A Disney Resort & Spa on Oahu; and Grand Wailea, Andaz Maui and Four Seasons Resort Maui on Maui.
“If a client wants quiet, relaxing and green, I know where to send them,” Placek said. “If they want adventure and volcanoes, I know where to send them.”
While not every advisor can spend more than two weeks researching a destination, Placek encourages her peers to be open to something similar, even on a small scale.
“Don’t be afraid of going out and doing something new,” she said. “What you invest in your business won’t ever not be worth it.”
She has her sights set on another research trip for next year — most likely to the Dominican Republic — because she believes that first-hand experience is one of the most powerful tools an advisor can have.
“You can Google anything, and you can watch videos or use AI,” she said. “But actually going and doing it gives you credibility. It gives you confidence. And there are things you can only learn by being there.”
