An occupational hazard of planning other people’s travel is that one does occasionally become almost numb to how beautiful the actual experience can be. This was a case in point after 18 months of pandemic related cancelations, reshuffles, pivots and night terrors over clients’ testing requirements, ever changing entrance requirements, mask mandates and last minute flight delays. So I did something new, something revolutionary and something I haven’t done in over 5 years – I took a true family vacation.

Having collaborated with two colleagues to cover each and every client need while I was unplugged, after multiple conference calls and e-meetings to assure that every eventuality was covered, I put on an actual “out of office” reply and stepped into United’s amazing Polaris product for an eight hour nap. We emerged into ethereal sunlight, with lush tropical greens and cool ocean blues so vivid that it all almost seemed fake.

We began our trip with two nights at the Four Seasons Ko’Olina in Oahu. This is my recommendation for most travelers to Hawaii – having a couple of days as a springboard to adjust to the time difference in the lap of luxury just makes good sense, but more importantly, getting to experience the awe-inspiring memorial at Pearl Harbor is an important part of the Hawaiian experience. We toured with a private guide from Blue Hawaii who helped make our time at the memorial even more interactive, and followed it up with a city tour, a trip to the King’s Palace, and a sneaky stop for the best hidden shaved ice spot the city has to offer.

Our next stop was Maui, where we lived like celebrities in an over the top private residence at the Andaz Maui in Wailea. This three bedroom villa had a balcony that framed out some of the most epic sunsets any of us had ever seen. During our time in Maui we toured the Road to Hana with Kellen of Local Maui Tours and surfed the waves on black sand beaches and cliff jumped into secluded waterfall ponds, enjoyed a magnificent snorkel charter at the crater of Molokini with Trilogy and devoured exquisite dinners every single night. We fell in love with Maui!

We ended our trip on the Garden Isle of Kauai, where breathtaking cliffs overlooked the ocean at our private home (with plunge pool) on the 15th hole at Timers Kauai. Our private charter with Makana Tours blew our minds when we pulled up next to several pods of dolphins who put on quite a show just for us. We enjoyed some recreation and relaxation at the pool, spa and on the links – and couldn’t get enough of the lush tropical views from every angle.

Not to get too meta, but there’s something truly fantastic about actually experiencing a trip that you’ve planned countless times for other people, and actually vacationing (vs working furtively from my phone while the rest of my family enjoys leisure time) was a crucial reminder of why I love designing travel and being trusted with my clients most valuable memories.