Larry Jackson spent roughly three decades living in the Aloha State, but he didn't put his local's knowledge to work as a Hawaii travel advisor until he moved nearly 5,000 miles away to Melbourne, Fla.
Jackson first visited the islands while in the U.S. Air Force, and when his service ended he decided to stay. He worked as a manager with Merrill Lynch and his closest connection to travel advisor work was assisting with planning and arrangements for business events.
"When you live in Hawaii, everyone comes to see you, so my wife and I learned to become tour guides by showing friends and family around," he said. "And we saw the tourists who didn't have that -- who come on big buses and they get off the bus, snap a picture and get back on the bus. They move like cattle."
In 2000 he moved to Florida and in 2003, he and his wife, Lynda Jackson, started their travel advisor business Cruise Holidays of Viera and later launched a subsidiary focused on the islands, Hawaii Boutique Escapes.
Even though they moved to the Atlantic Coast, the Jacksons still have family in Hawaii and return at least twice a year, maintaining their knowledge of the latest activities and products.
"We fell in love with Hawaii and we wanted to share it with other people," Larry Jackson said. "A lot of tourists who are shuttled around and go to the same places are missing 80% of what Hawaii is all about. We wanted to help people experience Hawaii the way a local would."
They also quickly realized that they could dispel many common myths held on the U.S. mainland about travel to Hawaii.
"I've heard it all: Do I need a passport? Can I use U.S. money? Is there cellphone coverage?" Jackson said. "Those are just some of the misconceptions we get."
About six years ago Hawaii Boutique Escapes started offering a special annual cruise package that the Jacksons personally tailored. A group of no more than 18 travelers led by the couple spend 12 days touring Oahu, Maui, Hawaii Island and Kauai, flying in and out of Honolulu and moving between the islands aboard Norwegian Cruise Line's Pride of America.
"We like to limit the group size to that number because then we can use the minibuses. So you can go to some places the bigger buses can't go, and you also don't spend your whole day getting on and off the bus," Jackson said. "It also means you can go to the local restaurants and everyone can order off the menu, instead of being stuck with a group package and fixed menu."
Along the way, the Jacksons have refined the itinerary. Guests on the trip the first few years felt the Oahu schedule was too packed, so they added a third day on Hawaii's most populous island to give people time to relax and pick out their own activities.
"A lot of our business is older people who have dreamed about Hawaii for a long time and have never taken the plunge," Jackson said. "The cruise is a great way to see a lot of what Hawaii has to offer on four different islands."
While increased flights out of the western United States and the entry of Southwest into the market have boosted competition and pushed prices down on the Pacific side, Jackson says the East Coast has seen no such relief in airfare.
"One issue from the East Coast for travelers going to Hawaii will always be the length of flights, and costs have gone up this last year," he said.
They are constantly reassessing the package components and tours, like adjusting their Hawaii Volcanoes National Park tour after so much changed during the 2018 eruptions.
"We had to redo that tour, because some stuff is not available or disappeared." Jackson said. "The active lava is gone, but there are other sites of interest. And on Haleakala on Maui they changed the system for group tours and sunrise entry, so we had to switch vendors."
While the April 2020 cruise tour has sold out, Jackson said he can arrange a similar package (but without their in-person guidance) for anyone headed to the islands.
"They can do everything we do on their own with just some minor adjustments depending on dates and time of year," Jackson said. "In that case, we can also make changes, look at different providers, and add what they are most interested in. We give them driving instructions and other tips so they can become their own tour guides."