Third Time's the Deepest: How Karrie Szabo Finally Unlocked Hawaii on Her Third Visit

There is a particular kind of confidence that comes with returning somewhere you love. You know the rhythms, the landmarks, the feel of the light in the late afternoon. You stop being a tourist and start being something closer to a regular. For travel advisor Karrie Szabo, Hawaii has always been that place. She has loved it, recommended it, and returned to it. But it was on her third trip, two weeks split between Oahu and Maui with her husband, that she finally felt she had truly seen it.

The secret, as it turns out, was not a new resort or a private guide. It was a rental car and an app most travelers have never heard of.

Going Deeper, Not Wider

Szabo has always known Hawaii's appeal. The scenery is extraordinary, the food is exceptional, the pace is restorative. She knew all of this before she boarded her flight. What she did not know was how much of the islands she had been missing. Renting a car on this trip changed everything. Rather than being routed through the highlights on a schedule that belonged to someone else, she and her husband moved at their own pace, stopping where curiosity took them, lingering where the view demanded it. "We went at our own pace and stopped at some great places," she says, and there is something quietly freeing in the way she describes it, as though the car itself became the real itinerary.

To navigate both islands with confidence, Szabo turned to Guide Along, an audio tour app that delivers location-triggered commentary while you drive, essentially placing a knowledgeable local narrator in the passenger seat. The result was a journey that felt both spontaneous and expertly curated. "By using this app," she says, "I'm confident I saw the top sites of Maui and Oahu." That word, confident, carries real weight coming from an advisor who has visited twice before. It is not the enthusiasm of a first-timer dazzled by everything. It is the considered verdict of a professional who now knows she left nothing important behind.

The North Shore and a Ranch That Stopped Her in Her Tracks

Among the places the open road led Szabo was the North Shore of Oahu, a stretch of coastline legendary for its surf culture and sweeping natural beauty. Despite two previous trips to Hawaii, she had never made it there before. It was the kind of discovery that reminds even the most experienced traveler that familiarity is not the same as knowledge. "We went to the North Shore of Oahu," she says, "which was a place I had never been." For a repeat visitor, those words carry a particular resonance. Here was proof that a destination as well-known as Hawaii still holds quiet revelations for those willing to look for them.

But if the North Shore was a discovery, Kualoa Ranch was the emotional peak of the entire trip. Tucked into a dramatic valley on Oahu's windward coast, Kualoa Ranch is a place of sweeping green mountains, ancient fishponds, and cinematic grandeur. It has served as the backdrop for some of Hollywood's most iconic productions, but in person, no amount of prior knowledge quite prepares you for the scale of it. Szabo, a traveler who chooses her words with the economy of someone who has described many beautiful places, reaches for the simplest and most complete of them. "I also really loved the Kualoa Ranch in Oahu," she says, "and it was amazing." The word lands without decoration and needs none. From someone on her third Hawaii trip, amazing means exactly that.

A Blueprint Built from Experience

One of the things that separates a great travel advisor from a good one is the ability to translate personal experience into practical guidance. Szabo returned from Hawaii not just with memories but with a field-tested itinerary she is ready to put to work for her clients. Her recommendation is precise and purposeful. "I will send them to Oahu for three nights," she says, "get in and see the sites, Pearl Harbor, Kualoa Ranch, North Shore, some great restaurants, and then island hop to a different place." It is the kind of advice that could only come from someone who has done it, not from a brochure or a destination overview, but from three personal trips and the hard-won knowledge of what actually fits, what actually resonates, and what actually leaves a traveler feeling they have done the place justice.

For Szabo, Hawaii is the ideal destination for travelers who love the outdoors, crave beautiful scenery, enjoy excellent food, and want a vacation that feels genuinely relaxed. The islands also offer outstanding golf courses, another draw for clients who like their downtime to come with a fairway view. Pearl Harbor remains an essential stop, a place of deep historical significance that grounds the visit in something more than leisure. Taken together, Szabo's Hawaii is a destination with extraordinary range, capable of satisfying the adventurer, the history enthusiast, the golfer, and the traveler who simply wants to feel restored.

The Insider Details That Make the Difference

Beyond the itinerary itself, Szabo came home with the kind of granular, lived-in tips that never appear in destination guides. Chief among them is her recommendation to download Guide Along before arrival. Paired with a rental car, the app effectively democratizes the experience of having a local expert on hand, without the rigidity of a scheduled tour. For clients who want freedom without the anxiety of missing something important, it is a genuinely elegant solution.

There is also a travel logistics tip that speaks to Szabo's instinct for thinking ahead. On the way to Hawaii, she and her husband built in an overnight layover in Vancouver, breaking the journey into two manageable legs. "We also had a layover in Vancouver overnight," she explains, "so it broke up the flight and we adjusted to the time change easier." It is a small thing, and that is precisely the point. The clients who arrive in Honolulu feeling refreshed and ready rather than exhausted and disoriented are the ones whose trips begin well and stay that way.

Always in the Field

For Szabo, Hawaii is not a chapter that has closed. It is a destination she will return to, recommend with conviction, and continue to refine her understanding of. And she will not be waiting long for her next adventure. Her calendar is already full. A cruise to the Caribbean aboard MSC from Galveston in Texas is on the near horizon, followed by a Princess cruise to the Caribbean departing from Orlando. Then, in June, she sets sail on a Royal Caribbean cruise to Europe, with time built in after the voyage to explore on land. It is the schedule of an advisor who is always in the field, always gathering the first-hand knowledge that makes her recommendations worth trusting.

Hawaii, for Szabo, has become something more than a favourite destination. It is proof that going back is not the same as standing still, and that the traveler who returns with fresh eyes and the right tools will always find something new waiting. Her third trip was not a repetition. It was, finally, the full picture.