Nearly every weekend, Jay-R Kaawa boards a flight between Maui and Molokai. The trips are not usually for work; they are for family.
Kaawa, head of Summer and Extended Learning at Kamehameha Schools Maui, regularly travels home to Molokai to care for her father, who is living with dementia. At least once a month, she and her siblings help fly him to Maui or Oʻahu for appointments and support. Other times, she makes the trip to check on him, spend time with him and help manage his care. For Kaawa, transportation is not a convenience. “It is a necessity. We need reliable air transportation. Bottom line,” she said.
Her story is one shared by families across Maui Nui who routinely travel between Molokai, Lānaʻi, Maui and Oʻahu for health care, work and time with loved ones. That reality is why many residents are paying close attention to Lānaʻi Air’s plans to expand service to Molokai.
The airline, which began as a charter service connecting Honolulu and Lānaʻi, has evolved over the past several years. Originally created to transport visitors to Lānaʻi, the company expanded public ticket sales in 2024 and now markets itself as another option for island residents. Earlier this year, Lānaʻi Air announced plans to begin service to Molokai, adding a second commercial air carrier to an island that has spent years with limited transportation options.
The expansion marks the latest step in the company’s growth. The airline intends to operate four daily roundtrip flights between Molokai and Honolulu using their 19-seat Cessna SkyCourier aircraft. They have been promoting the aircraft’s larger cabin and accessibility features while emphasizing its goal of improving transportation options for residents traveling for healthcare, education, work and family obligations.
Kaawa flies home nearly every weekend and estimates she spends at least $220 on airfare each trip. Sometimes, she said, a one-way ticket can cost more than $200. “Just from an economic standpoint, having a competitor will hopefully bring down fares,” she said. While she considers herself fortunate to be able to afford those trips, she worries about residents who cannot.
“If one plane is out of commission, the whole schedule is messed up,” she said. Despite those challenges, Molokai residents continue to find ways to get where they need to go.
“We’re resourceful in that way, we always find ways to make things work,” Kaawa said. Some residents catch rides on boats operated by friends or family members. Others coordinate travel with fishermen making trips between islands. For many, finding transportation is simply part of daily life. “We’re going to make do with what we have, but that doesn’t mean it’s right,” she said.
Accessibility is another concern. Because of his dementia, Kaawa’s father often struggles boarding smaller commuter aircraft. While he remains physically capable, navigating the tight spaces of a small plane can be difficult. “I literally have to hold his head down and crawl him into the plane,” she said.
At least once a month, Kaawa and her siblings fly their father to Maui or Oʻahu so he can spend time with family and receive additional support. While neighbors and family friends often help transport him when needed, she worries about the burden placed on others.
“I would feel much better knowing it’s a plane that doesn’t seem so cramped,” she said. For families caring for kūpuna and loved ones with medical conditions, the size of the aircraft matters. Many residents travel with walkers, wheelchairs, oxygen equipment or other medical devices. Others simply find boarding small commuter planes difficult. Kaawa believes a larger aircraft could make a meaningful difference for those families.
Maui lifeguard Kaipo Garcia has seen firsthand how important reliable transportation can be during some of life’s most difficult moments. Inter-island travel is part of his family’s routine. His sister lives on Lānaʻi and regularly travels because her daughter is undergoing cancer treatment.
“She flies every week because my niece has cancer,” Garcia said. Like many families living on smaller islands, they rely on flights to access specialized healthcare services unavailable at home.
Garcia has also heard stories from residents whose travel plans were disrupted by delays and cancellations. “They were missing their appointments,” he said. “They’d make their doctor appointments based on the [flight’s] arrival time and then delays would happen.”
The importance of reliable transportation became personal earlier this year when Garcia’s father passed away on Lānaʻi.
Living on Maui, he immediately searched for a flight home. His father died shortly before 8:00 p.m. Garcia was able to book a last-minute flight and arrive in time to be with his family. “I made reservations last minute,” he said. “At least I got there.” The flight allowed him to help carry his father from his bed to the hearse.
For Garcia, that experience reinforced something many Molokai and Lānaʻi families already understand. Transportation is about much more than getting from one island to another. It is about being present when family needs you most.
Community members have also pointed to another reason they are optimistic about Lānaʻi Air’s expansion: familiar faces. During community outreach events, residents met airline employees who previously worked for Island Air, a carrier that served neighbor island communities for decades.
Many Molokai residents already knew them. That familiarity, Kaawa said, helped build trust. “It’s local folks that we know and have seen frequently while traveling,” she said.
Some residents also see the airline’s hiring of former Island Air employees as a sign that local knowledge and experience remain part of the company’s approach. While questions remain about how the expansion will ultimately affect the community, many residents say they are hopeful.
No airline is immune from weather disruptions, maintenance issues or operational challenges. But for residents accustomed to limited options, another carrier represents something many have wanted for years: a choice.
“We’re grateful for what we have,” Kaawa said. “But we’re ready for another option.”
This article is reprinted with permission from OHA's Ka Wai Ola newspaper: "Molokaʻi is Ready For Another Option" by Philamer Felicitas, in its July 2026 issue, Vol. 43 No. 7. Read more at kawaiola.news.
